Injectable pharmaceutical formulations

Abstract

Provided herein are injectable pharmaceutical formulations, methods for their production, kits, and uses thereof in the treatment of diseases or disorders. The injectable pharmaceutical formulations include a psychopharmaceutical agent, a release modifier, and an aqueous vehicle. The pharmaceutical formulations allow for a time-restricted temporal controlled-release of the psychopharmaceutical agent upon administration by injection such as subcutaneous injection. The diseases or disorders treatable with the pharmaceutical formulations include, for example, neuropsychiatric diseases or disorders or inflammatory diseases or disorders, such as a central nervous system (CNS) disorder and / or psychological disorder, including those associated with a 5-HT2 receptor.

Description

[0001] INJECTABLE PHARMACEUTICAL FORMULATIONS CROSS-REFERENCE This application claims priority to U.S. Provisional Application No. 63 / 464,265, filed on 5 May 5, 2023, U.S. Provisional Application No. 63 / 507,062, filed on June 8, 2023, and U.S. Provisional Application No. 63 / 599,483, filed on November 15, 2023, each incorporated herein by reference in their entireties. FIELD 10 The present disclosure relates generally to injectable pharmaceutical formulations comprising a psychopharmaceutical agent and uses in the treatment of neuropsychiatric diseases or disorders or inflammatory diseases or disorders, such as a central nervous system (CNS) disorder and / or psychological disorder, including those associated with a 5-HT2receptor. 15 BACKGROUND The pharmacological treatment of mood, anxiety, trauma-related, and substance use disorders with currently available drugs is characterized by (partial) ineffectiveness. A substantial proportion of patients fail to recover despite treatment with therapeutic doses and various augmentation agents, and patients who do achieve symptomatic relief often experience 20 burdensome adverse effects and run a serious risk of suicidal behavior or completed suicide. In the last three decades, there has been a resurgence of interest in psychedelic, dissociative, and entactogenic drug research. Various such drugs when combined with psychotherapy, have shown early, but robust effectiveness following a limited number of administrations (typically 1-3 drug assisted psychotherapy sessions). For instance, the entactogen 25 methylenedioxymethamphetamine (MDMA) has recently passed the first phase-III trial in patients with PTSD [Mitchell JM, et al. MDMA-assisted therapy for severe PTSD: a randomized, double- blind, placebo-controlled phase 3 study. Nat Med. 2021;27: 1025–1033]. Lysergic acid diethylamide (LSD) has shown clinical promise in alcohol use disorder [Chi T, Gold JA. A review of emerging therapeutic potential of psychedelic drugs in the treatment of psychiatric illnesses. J 30 Neurol Sci. 2020, 411: 116715; Fuentes JJ, et al. Therapeutic Use of LSD in Psychiatry: A Systematic Review of Randomized-Controlled Clinical Trials. Front Psychiatry.2020;10: 1–14]. In the tryptamine class of serotonergic psychedelics, psilocybin (the active ingredient in ‘magic 1

[0002] mushrooms’) has shown promise in a phase II trial for MDD, end of life anxiety [Griffiths RR, et al. Psilocybin produces substantial and sustained decreases in depression and anxiety in patients with life-threatening cancer: A randomized double-blind trial. J Psychopharmacol.2016;30: 1181– 1197], and smoking cessation [Garcia-Romeu A, Griffiths RR, Johnson MW. Psilocybin- 5 occasioned mystical experiences in the treatment of tobacco addiction. Curr Drug Abuse Rev. 2014;7: 157–164; de Veen BTH, et al. Psilocybin for treating substance use disorders? Expert Rev Neurother.2017;17: 203–212; Johnson MW, et al. Pilot study of the 5-HT2AR agonist psilocybin in the treatment of tobacco addiction. J Psychopharmacol.2014;28: 983–992; and Johnson MW, Garcia-Romeu A, Griffiths RR. Long-term follow-up of psilocybin-facilitated smoking cessation. 10 Am J Drug Alcohol Abuse. 2017;43: 55–60]; and N,N-dimethyltryptamine (DMT; also referred to as 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine) (usually as an active ingredient in ayahuasca) has shown promising effects on mood [Vollenweider FX, Preller KH. Psychedelic drugs: neurobiology and potential for treatment of psychiatric disorders. Nat Rev Neurosci. 2020;21: 611–624; Barker SA. N,N-dimethyltryptamine (DMT), an endogenous hallucinogen:15 Past, present, and future research to determine its role and function. Front Neurosci.2018;12: 1– 17; and Strassman RJ, et al. Dose-response study of N,N-Dimethyltryptamine in humans II: Subjective effects and preliminary results of a new rating scale. Arch Gen Psychiatry. 1994;51: 98–108] and potentially, addictions [Thomas G, et al. Ayahuasca-assisted therapy for addiction: Results from a preliminary observational study in Canada. Curr Drug Abuse Rev.2013; Oliveira- 20 Lima AJ, et al. Effects of ayahuasca on the development of ethanol-induced behavioral sensitization and on a post-sensitization treatment in mice. Physiol Behav.2015;142: 28–36; Nolli LM, et al. Effects of the hallucinogenic beverage ayahuasca on voluntary ethanol intake by rats and on cFos expression in brain areas relevant to drug addiction. Alcohol.2019; Fábregas JM, et al. Assessment of addiction severity among ritual users of ayahuasca. Drug Alcohol Depend. 25 2010;111: 257–261; Argento E, et al. Exploring ayahuasca-assisted therapy for addiction: A qualitative analysis of preliminary findings among an Indigenous community in Canada. Drug Alcohol Rev.2019;38: 781–789; and Noorani T, et al. Psychedelic therapy for smoking cessation: Qualitative analysis of participant accounts. J Psychopharmacol.2018;32: 756–769]. DMT’s binding profile is well characterized. DMT acts on numerous ionotropic and 30 metabotropic receptors. It binds with affinity to 5-hydroxytryptamine-(5-HT)1A, 5-HT2A, 5-HT2C, and serotonin transporter (SERT) receptors from the 5-HT / serotonin family [Cameron LP, Olson DE. Dark Classics in Chemical Neuroscience: N,N-Dimethyltryptamine (DMT). ACS Chem 2

[0003] Neurosci. 2018;9: 2344–2357]. DMT is a potent agonist at the 5-HT2A receptor, through which (not unlike other serotonergic psychedelics) it exerts many subjective, visual, and potentially therapeutic effects [Cameron LP, Olson DE. Dark Classics in Chemical Neuroscience: N, N- Dimethyltryptamine (DMT). ACS Chem Neurosci. 2018;9: 2344–2357; Carbonaro TM, Gatch 5 MB. Neuropharmacology of N,N-dimethyltryptamine. Brain Res Bull.2016;126: 74–88].5-HT2A activation has also been linked with increased synaptic plasticity [Ly C, et al. Psychedelics Promote Structural and Functional Neural Plasticity. Cell Rep.2018;23: 3170–3182; Ly C, et al. Transient Stimulation with Psychoplastogens Is Sufficient to Initiate Neuronal Growth. ACS Pharmacol Transl Sci.2020; and Inserra A, De Gregorio D, Gobbi G. Psychedelics in Psychiatry: 10 Neuroplastic, Immunomodulatory, and Neurotransmitter Mechanisms. Pharmacol Rev. 2021;73: 202–277]. Additionally, DMT binds to other receptors, including trace amine-associated receptors (TAARs) and the sigma-1 receptor, potentially contributing to its neuroprotective plasticity enhancing effects [Carbonaro TM, Gatch MB. Neuropharmacology of N,N-dimethyltryptamine. Brain Res Bull. 2016;126: 74–88; Barker SA. N, N-dimethyltryptamine (DMT), an endogenous 15 hallucinogen: Past, present, and future research to determine its role and function. Front Neurosci. 2018;12: 1–17]. Despite high potencies at serotonin 5-HT2Rs, the therapeutic value of certain tryptamine psychedelics has been hampered by their accelerated metabolism in the liver and gastrointestinal tract most notably by monoamine oxidase (MAO) enzymes. For example, DMT is not orally 20 active—it is converted to inactive metabolites before sufficient brain penetration can occur. For this reason, DMT is typically dosed with a monoamine oxidase inhibitor (as is the case in ayahuasca) to prolong its duration of action. Likewise, 5-methoxy-N,N-dimethyltryptamine (5- MeO-DMT) lacks oral bioavailability and is instead ordinarily vaporized and inhaled to produce psychedelic effects. Such MAO-mediated metabolism is also believed to contribute to high 25 variability in the pharmacokinetic (PK) profiles of various tryptamines in humans, including significant patient-to-patient pharmacokinetic variability after oral psilocybin administration and intravenous (IV) administration of DMT. Additionally, in marked contrast to the hours-long subjective effects of other serotonergic psychedelics such as LSD (8 to 20 hour duration of action) and psilocybin (6 to 8 hour duration of 30 action), the duration of action time course of short-acting tryptamine psychedelics such as DMT and 5-MeO-DMT administered as a bolus to humans via inhalation or intravenous or intramuscular injection is brief—so short as to limit their use in effective therapies. For DMT, the onset of 3

[0004] subjective effects on perception and consciousness (sometimes referred to as the “psychedelic state”) are rapid and overwhelming, with profound and intense visual peak experiences noted within 2 minutes of administration. The psychedelic state dissipates rapidly, with subjective effects returning to baseline (or close to) following roughly 20 to 30 minutes post administration 5 [Strassman RJ, Qualls CR, Uhlenhuth EH, Kellner R. Dose-response study of N,N- Dimethyltryptamine in humans II: Subjective effects and preliminary results of a new rating scale. Arch Gen Psychiatry. 1994;51: 98–108]. On one hand, the short time course spent in the psychedelic state is seen as therapeutically limiting and makes sophisticated granular assessment of pharmacodynamic (PD) effects and safety profiles inherently difficult. On the other hand, short- 10 acting tryptamine psychedelics are potentially more controllable and clinically scalable compared to longer-acting psychedelic compounds such as LSD and psilocybin, which often require 7 to 8 hours or more of supervised clinical observation of a patient before discharge. To improve treatment profiles of DMT by avoiding excessive drug levels associated with bolus IV injections or inhalation administration, and to provide more scalable duration of effects 15 (e.g., peak effects of about 30 to 120 minutes), continuous-controlled IV infusions have been studied [Gallimore AR, Strassman RJ. A model for the application of target-controlled intravenous infusion for a prolonged immersive DMT psychedelic experience. Front Pharmacol. 2016;7: 1– 11]. DMT infusions administered over about 90 minutes allowed for expanding, in a time- controlled manner, the exposure while maximizing the effects of the drug. However, infusion 20 protocols (e.g., where the patient is administered the drug over prolonged periods such as over an hour or longer) are not generally clinically practical, as they require significant clinical resources and personnel that represent major challenges in scaling up the treatment for larger populations of patients. Consequently, there is a need for new formulations and delivery approaches which retain 25 the pharmacokinetic and pharmacologic benefits of intravenous infusion administration (i.e., provide a target-controlled duration of peak effects lasting about 30 to 120 minutes), yet offer an alternative that is clinically practical, convenient for the patients, and economical for sponsors and service providers. 30 SUMMARY Accordingly, the present disclosure is based at least in part on the identification of novel injectable pharmaceutical formulations, kits, and treatment methods which allow for a time- 4

[0005] restricted temporal controlled-release of a psychopharmaceutical agent. In the case of short-acting tryptamine psychedelics such as DMT, 5-MeO-DMT, and their analogs (e.g., deuterated analogs), this controlled-release would provide a duration of peak effects of about 30 to 120 minutes to maximize therapeutic benefits and reduce side effects. By doing so, the injectable pharmaceutical 5 formulations extend the time the patient spends in the psychedelic state compared to bolus IV injection of the same tryptamine psychedelic, without overextending the release and the resulting duration of peak effects beyond about 120 minutes to avoid the prolonged supervised clinical observation requirements imposed by longer-acting psychopharmaceutical agents such as LSD and psilocybin. 10 These and other objects, which will become apparent during the following detailed description, have been achieved by the inventors’ discovery of novel injectable pharmaceutical formulations containing a psychopharmaceutical agent in combination with specific release modifiers which can be administered as a bolus injection, including as a subcutaneous bolus injection, that display a tunable and linear release of the psychopharmaceutical agent. In the case 15 of tryptamine psychedelics such as DMT, 5-MeO-DMT, and their analogs (e.g., deuterated analogs), a desirable controlled-release can be achieved to mimic the clinically advantageous 30 to 120 minute peak effect profile that has only been achieved by IV infusion of such psychopharmaceutical agents. Thus, the present disclosure provides: 20 (1) An injectable pharmaceutical formulation, comprising: a psychopharmaceutical agent; a hyaluronate salt; and an aqueous vehicle; wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of a 25 compound of Formula (I) or a stereoisomer, solvate, or prodrug thereof, 5

[0006] wherein: X1and X2are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted 5 alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; Y1 and Y2 are independently selected from the group consisting of hydrogen and deuterium; R2is selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or 10 substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; R4and R5are independently selected from the group consisting of hydrogen, deuterium, hydroxyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy, unsubstituted or 15 substituted alkylthio, and unsubstituted or substituted acyloxy; R6and R7are independently selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; and 20 R8 and R9 are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, or alternatively R8 and R9 together with the nitrogen atom attached thereto are optionally 6

[0007] joined to form an unsubstituted or substituted heterocycloalkyl. (2) The injectable pharmaceutical formulation of (1), wherein the compound has a structure of Formula (II), or a stereoisomer, solvate, or prodrug thereof 5 wherein: X1 and X2 are independently hydrogen or deuterium, Y1 and Y2 are independently hydrogen or deuterium, each Z1is independently hydrogen or deuterium, 10 each Z2 is independently hydrogen or deuterium, and R2, R4, R5, R6, and R7 are independently hydrogen or deuterium. (3) The injectable pharmaceutical formulation of (1) or (2), wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of at least one compound 15 selected from the group consisting of (I-1), (I-2), 7

[0008] (I-11), and (I-12), or a stereoisomer, solvate, or prodrug thereof. (4) The injectable pharmaceutical formulation of any one of (1) to (3), wherein the 5 psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8). (5) The injectable pharmaceutical formulation of any one of (1) to (3), wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- 10 bis(methyl-d3)ethan-1-amine-1,1-d2(I-6). (6) The injectable pharmaceutical formulation of any one of (1) to (3), wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- dimethylethan-1-amine-1,1-d2 (I-2). 15 (7) The injectable pharmaceutical formulation of any one of (1) to (3), wherein the psychopharmaceutical agent is an active salt mixture comprising: (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I-8); and (ii) a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- 20 amine-1,2,2-d3(I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11). (8) The injectable pharmaceutical formulation of (7), wherein the active salt mixture comprises (i) from 60% to 99% by weight of the pharmaceutically acceptable salt of 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I-8), based on a total weight of the active salt 25 mixture; and (ii) from 1% to 40% by weight, in sum, of the pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2-(1H- 9

[0009] indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11), based on a total weight of the active salt mixture. (9) The injectable pharmaceutical formulation of (1), wherein the compound has a structure 5 of Formula (III), or a stereoisomer, solvate, or prodrug thereof wherein: X1 and X2 are independently hydrogen or deuterium, Y1and Y2are independently hydrogen or deuterium, 10 each Z1 is independently hydrogen or deuterium, each Z2 is independently hydrogen or deuterium, each Z3is independently hydrogen or deuterium, and R2, R4, R6, and R7 are independently hydrogen or deuterium. 15 (10) The injectable pharmaceutical formulation of (1) or (9), wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of at least one compound selected from the group consisting of 10

[0010] (I-37), (I-38), or a stereoisomer, solvate, or prodrug thereof. (11) The injectable pharmaceutical formulation of any one of (1), (9), or (10) wherein the 5 psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(5-methoxy-1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-20). (12) The injectable pharmaceutical formulation of any one of (1) or (9) to (11), wherein the psychopharmaceutical agent is an active salt mixture comprising: (i) a pharmaceutically10 acceptable salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I- 20); and (ii) a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol-3-yl)- N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-22) and / or 2-(5-methoxy-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-23). 15 (13) The injectable pharmaceutical formulation of any one of (1) to (12), wherein the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt. (14) The injectable pharmaceutical formulation of any one of (1) to (13), wherein the 20 pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, or a succinate salt. (15) The injectable pharmaceutical formulation of any one of (1) to (14), wherein a concentration of the psychopharmaceutical agent by weight (in terms of free base equivalence) per total volume of the pharmaceutical formulation is about 1 mg / mL to about 100 mg / mL. 25 (16) The injectable pharmaceutical formulation of any one of (1) to (15), wherein a concentration of the psychopharmaceutical agent by weight (in terms of free base equivalence) per 14

[0011] total volume of the pharmaceutical formulation is about 10 mg / mL to about 50 mg / mL. (17) The injectable pharmaceutical formulation of any one of (1) to (16), wherein the hyaluronate salt is sodium hyaluronate. 5 (18) The injectable pharmaceutical formulation of any one of (1) to (17), wherein the hyaluronate salt has a weight average molecular weight of about 500 kDa to about 2,000 kDa. (19) The injectable pharmaceutical formulation of any one of (1) to (18), wherein the 10 hyaluronate salt has a weight average molecular weight of about 1,000 kDa to about 1,800 kDa. (20) The injectable pharmaceutical formulation of any one of (1) to (19), wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 2% (w / v). 15 (21) The injectable pharmaceutical formulation of any one of (1) to (20), wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 1% (w / v). 20 (22) The injectable pharmaceutical formulation of any one of (1) to (21), wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 0.75% (w / v). (23) The injectable pharmaceutical formulation of any one of (1) to (22), wherein a 25 concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 0.5% (w / v). (24) The injectable pharmaceutical formulation of any one of (1) to (23), wherein the aqueous vehicle comprises water and sodium chloride. 30 (25) The injectable pharmaceutical formulation of (24), wherein the pharmaceutical formulation comprises sodium chloride at a concentration, in terms of weight per total volume of 15

[0012] the pharmaceutical formulation, of about 0.1% to about 0.8% (w / v). (26) The injectable pharmaceutical formulation of any one of (1) to (25), which has a pH of about 3 to about 7. 5 (27) The injectable pharmaceutical formulation of any one of (1) to (26), which has an osmolality of about 150 mOsm / kg to about 600 mOsm / kg. (28) The injectable pharmaceutical formulation of any one of (1) to (27), which has a 10 viscosity of less than about 3,000 cP. (29) The injectable pharmaceutical formulation of any one of (1) to (28), which is suitable for subcutaneous injection. 15 (30) The injectable pharmaceutical formulation of any one of (1) to (29), which is suitable for bolus subcutaneous injection. (31) The injectable pharmaceutical formulation of any one of (1) to (30), wherein the injectable pharmaceutical formulation provides a duration of peak effects of about 30 minutes to 20 about 120 minutes after being administered to a human subject via bolus subcutaneous injection. (32) A kit suitable for preparing the injectable pharmaceutical formulation of any one of (1) to (31), the kit comprising: (a1) a first solution comprising the psychopharmaceutical agent and the aqueous vehicle; 25 and (b1) a second solution comprising the hyaluronate salt and the aqueous vehicle. (33) A method of treating a central nervous system (CNS) disorder and / or psychological disorder in a subject in need thereof, comprising administering to the subject a therapeutically 30 effective amount the injectable pharmaceutical formulation of any one of (1) to (31). (34) The method of (33), wherein the CNS disorder and / or psychological disorder is a 16

[0013] substance use disorder. (35) The method of (34), wherein the substance use disorder is alcohol use disorder. 5 (36) The method of (33), wherein the CNS disorder and / or psychological disorder is an anxiety disorder. (37) The method of (36), wherein the anxiety disorder is generalized anxiety disorder (GAD). 10 (38) The method of (37), wherein the generalized anxiety disorder is comorbid with depression. (39) The method of (36), wherein the anxiety disorder is social anxiety disorder. 15 (40) The method of (33), wherein the CNS disorder and / or psychological disorder is a depressive disorder. (41) The method of (40), wherein the depressive disorder is major depressive disorder 20 (MDD) or treatment-resistant depression (TRD). (42) The method of (33), wherein the CNS disorder and / or psychological disorder is at least one selected from the group consisting of post-traumatic stress disorder (PTSD), major depressive disorder (MDD), treatment-resistant depression (TRD), suicidal ideation, suicidal 25 behavior, melancholic depression, atypical depression, dysthymia, non-suicidal self-injury disorder (NSSID), bipolar and related disorders, obsessive-compulsive disorder (OCD), generalized anxiety disorder (GAD), acute psychedelic crisis, social anxiety disorder, alcohol use disorder, opioid use disorder, amphetamine use disorder, nicotine use disorder, cocaine use disorder, Alzheimer’s disease, cluster headache and migraine, attention deficit hyperactivity 30 disorder (ADHD), pain, aphantasia, childhood-onset fluency disorder, major neurocognitive disorder, mild neurocognitive disorder, chronic fatigue syndrome, Lyme disease, gambling disorder, anorexia nervosa, bulimia nervosa, binge-eating disorder, pedophilic disorder, 17

[0014] exhibitionistic disorder, voyeuristic disorder, fetishistic disorder, sexual masochism or sadism disorder, transvestic disorder, sexual dysfunction, and obesity. (43) The method of any one of (33) to (42), wherein the injectable pharmaceutical 5 formulation is administered via injection. (44) The method of any one of (33) to (43), wherein the injectable pharmaceutical formulation is administered via subcutaneous injection. 10 (45) The method of any one of (33) to (44), wherein the injectable pharmaceutical formulation is administered via bolus subcutaneous injection. (46) The method of (45), wherein the bolus subcutaneous injection provides a duration of peak effects of about 30 minutes to about 120 minutes after being administered. 15 (47) An injectable pharmaceutical formulation, comprising: a psychopharmaceutical agent; a carboxymethyl cellulose salt; and an aqueous vehicle; 20 wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of a compound of Formula (I) or a stereoisomer, solvate, or prodrug thereof, wherein: X1 and X2 are independently selected from the group consisting of hydrogen, deuterium, 18

[0015] unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; Y1 and Y2 are independently selected from the group consisting of hydrogen and 5 deuterium; R2is selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; 10 R4 and R5 are independently selected from the group consisting of hydrogen, deuterium, hydroxyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, and unsubstituted or substituted acyloxy; R6and R7are independently selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or 15 substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; and R8 and R9 are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, 20 unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, or alternatively R8 and R9 together with the nitrogen atom attached thereto are optionally joined to form an unsubstituted or substituted heterocycloalkyl. (48) The injectable pharmaceutical formulation of (47), wherein the carboxymethyl 25 cellulose salt is sodium carboxymethyl cellulose. (49) The injectable pharmaceutical formulation of (47) or (48), wherein the carboxymethyl cellulose salt has a weight average molecular weight of about 50 kDa to about 450 kDa. 30 (50) The injectable pharmaceutical formulation of any one of (47) to (49), wherein a concentration of the carboxymethyl cellulose salt by weight per total volume of the pharmaceutical formulation is from about 0.55% to about 1% (w / v). 19

[0016] (51) A kit suitable for preparing the injectable pharmaceutical formulation of any one of (47) to (50), the kit comprising: (a1) a first solution comprising the psychopharmaceutical agent and the aqueous vehicle; 5 and (b1) a second solution comprising the carboxymethyl cellulose salt and the aqueous vehicle. (52) A method of treating a central nervous system (CNS) disorder and / or psychological 10 disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount the injectable pharmaceutical formulation of any one of (47) to (50). (53) The method of (52), wherein the CNS disorder and / or psychological disorder is a substance use disorder. 15 (54) The method of (53), wherein the substance use disorder is alcohol use disorder. (55) The method of (52), wherein the CNS disorder and / or psychological disorder is an anxiety disorder. 20 (56) The method of (55), wherein the anxiety disorder is generalized anxiety disorder (GAD). (57) The method of (56), wherein the generalized anxiety disorder is comorbid with 25 depression. (58) The method of (55), wherein the anxiety disorder is social anxiety disorder. (59) The method of (52), wherein the CNS disorder and / or psychological disorder is a 30 depressive disorder. (60) The method of (59), wherein the depressive disorder is major depressive disorder 20

[0017] (MDD) or treatment-resistant depression (TRD). (61) The method of (52), wherein the CNS disorder and / or psychological disorder is at least one selected from the group consisting of post-traumatic stress disorder (PTSD), major 5 depressive disorder (MDD), treatment-resistant depression (TRD), suicidal ideation, suicidal behavior, melancholic depression, atypical depression, dysthymia, non-suicidal self-injury disorder (NSSID), bipolar and related disorders, obsessive-compulsive disorder (OCD), generalized anxiety disorder (GAD), acute psychedelic crisis, social anxiety disorder, alcohol use disorder, opioid use disorder, amphetamine use disorder, nicotine use disorder, cocaine use 10 disorder, Alzheimer’s disease, cluster headache and migraine, attention deficit hyperactivity disorder (ADHD), pain, aphantasia, childhood-onset fluency disorder, major neurocognitive disorder, mild neurocognitive disorder, chronic fatigue syndrome, Lyme disease, gambling disorder, anorexia nervosa, bulimia nervosa, binge-eating disorder, pedophilic disorder, exhibitionistic disorder, voyeuristic disorder, fetishistic disorder, sexual masochism or sadism 15 disorder, transvestic disorder, sexual dysfunction, and obesity. (62) The method of any one of (52) to (61), wherein the injectable pharmaceutical formulation is administered via injection. 20 (63) The method of any one of (52) to (62), wherein the injectable pharmaceutical formulation is administered via subcutaneous injection. (64) The method of any one of (52) to (63), wherein the injectable pharmaceutical formulation is administered via bolus subcutaneous injection. 25 (65) The method of any one of (52) to (64), wherein the bolus subcutaneous injection provides a duration of peak effects of about 30 minutes to about 120 minutes after being administered. 30 (66) An injectable pharmaceutical formulation, comprising: a psychopharmaceutical agent; a hyaluronate salt; and 21

[0018] an aqueous vehicle; wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of ketamine, or a stereoisomer, solvate, or prodrug thereof. 5 (67) The injectable pharmaceutical formulation of (66), wherein the pharmaceutically acceptable salt is an inorganic salt. (68) The injectable pharmaceutical formulation of (66) or (67), wherein the pharmaceutically acceptable salt is a hydrochloride salt. 10 (69) The injectable pharmaceutical formulation of any one of (66) to (68), wherein a concentration of the psychopharmaceutical agent by weight (in terms of free base equivalence) per total volume of the pharmaceutical formulation is about 1 mg / mL to about 100 mg / mL. 15 (70) The injectable pharmaceutical formulation of any one of (66) to (69), wherein a concentration of the psychopharmaceutical agent by weight (in terms of free base equivalence) per total volume of the pharmaceutical formulation is about 10 mg / mL to about 50 mg / mL. (71) The injectable pharmaceutical formulation of any one of (66) to (70), wherein the 20 hyaluronate salt is sodium hyaluronate. (72) The injectable pharmaceutical formulation of any one of (66) to (71), wherein the hyaluronate salt has a weight average molecular weight of about 500 kDa to about 2,000 kDa. 25 (73) The injectable pharmaceutical formulation of any one of (66) to (72), wherein the hyaluronate salt has a weight average molecular weight of about 1,000 kDa to about 1,800 kDa. (74) The injectable pharmaceutical formulation of any one of (66) to (73), wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation 30 is from about 0.1% to about 2% (w / v). (75) The injectable pharmaceutical formulation of any one of (66) to (74), wherein a 22

[0019] concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 1% (w / v). (76) The injectable pharmaceutical formulation of any one of (66) to (75), wherein a 5 concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 0.75% (w / v). (77) The injectable pharmaceutical formulation of any one of (66) to (76), wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation 10 is from about 0.1% to about 0.5% (w / v). (78) The injectable pharmaceutical formulation of any one of (66) to (77), wherein the aqueous vehicle comprises water and sodium chloride. 15 (79) The injectable pharmaceutical formulation of (78), wherein the pharmaceutical formulation comprises sodium chloride at a concentration, in terms of weight per total volume of the pharmaceutical formulation, of about 0.1% to about 0.8% (w / v). (80) The injectable pharmaceutical formulation of any one of (66) to (79), which has a pH 20 of about 3 to about 7. (81) The injectable pharmaceutical formulation of any one of (66) to (80), which has an osmolality of about 150 mOsm / kg to about 600 mOsm / kg. 25 (82) The injectable pharmaceutical formulation of any one of (66) to (81), which has a viscosity of less than about 3,000 cP. (83) The injectable pharmaceutical formulation of any one of (66) to (82), which is suitable for subcutaneous injection. 30 (84) The injectable pharmaceutical formulation of any one of (66) to (83), which is suitable for bolus subcutaneous injection. 23

[0020] (85) The injectable pharmaceutical formulation of any one of (66) to (84), wherein the injectable pharmaceutical formulation provides a duration of peak effects of about 30 minutes to about 120 minutes after being administered to a human subject via bolus subcutaneous injection. 5 (86) A kit suitable for preparing the injectable pharmaceutical formulation of any one of (66) to (85), the kit comprising: (a1) a first solution comprising the psychopharmaceutical agent and the aqueous vehicle; and 10 (b1) a second solution comprising the hyaluronate salt and the aqueous vehicle. (87) A method of treating a central nervous system (CNS) disorder and / or psychological disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the injectable pharmaceutical formulation of any one of (66) to (85). 15 (88) Use of the injectable pharmaceutical formulation of any one of (1) to (31) for treating a patient with a central nervous system (CNS) disorder and / or psychological disorder. (89) The injectable pharmaceutical formulation of any one of (1) to (31) for use in therapy. 20 (90) Use of the injectable pharmaceutical formulation of any one of (47) to (50) for treating a patient with a central nervous system (CNS) disorder and / or psychological disorder. (91) The injectable pharmaceutical formulation of any one of (47) to (50) for use in therapy. 25 (92) Use of the injectable pharmaceutical formulation of any one of (66) to (85) for treating a patient with a central nervous system (CNS) disorder and / or psychological disorder. (93) The injectable pharmaceutical formulation of any one of (66) to (85) for use in therapy. 30 BRIEF DESCRIPTION OF THE DRAWINGS 24

[0021] The forgoing paragraphs have been provided by way of general introduction and are not intended to limit the scope of the following claims. The described embodiments, together with further advantages, will be best understood by reference to the following detailed description when considered in conjunction with the accompanying drawings, wherein: 5 Fig. 1 illustrates a general synthetic route for making Compounds of Formula (I), e.g., compounds I-2 and I-6; Fig. 2 illustrates a general synthetic route for making Compounds of Formula (I), e.g., compounds I-1, I-4, I-5, and I-8; Fig.3 shows the percent drug release versus time profile of Formulations 1-6 compared to 10 control when subjected to the Dialysis—Drug Release Test; Fig. 4 shows the percent drug release versus time profile of Formulation 7 compared to control when subjected to the Dialysis—Drug Release Test; Fig. 5 shows the percent drug release versus time profile of Formulation 8 compared to control when subjected to the Dialysis—Drug Release Test; 15 Fig. 6 shows the percent drug release versus time profile of Formulation 9 compared to control when subjected to the Dialysis—Drug Release Test; Figs.7A and 7B show the percent drug release versus time profile of Formulations 10-12 compared to control when subjected to the Dialysis—Drug Release Test (Fig. 7A) and the corresponding first order release kinetic plot (Fig.7B); 20 Figs.8A and 8B show the percent drug release versus time profile of Formulations 13-15 compared to control when subjected to the Dialysis—Drug Release Test (Fig. 8A) and the corresponding first order release kinetic plot (Fig.8B); Figs.9A and 9B show the percent drug release versus time profile of Formulations 16-18 compared to control when subjected to the Dialysis—Drug Release Test (Fig. 9A) and the 25 corresponding first order release kinetic plot (Fig.9B); Figs.10A and 10B show the percent drug release versus time profile of Formulations 19- 21 compared to control when subjected to the Dialysis—Drug Release Test (Fig. 10A) and the corresponding first order release kinetic plot (Fig.10B); Fig.11 shows the percent drug release versus time profile of Formulations 22-27 compared 30 to control when subjected to the Dialysis—Drug Release Test; Figs. 12A and 12B show individual DMT-d10 plasma concentration-time curves in male Beagle dogs (animal IDs: 068M, 069M, 070M) after subcutaneous administration of DMT-d10at25

[0022] 0.1 mg / kg from control (Fig.12A) and Formulation 28 (Fig.12B); Figs.13A and 13B show mean DMT-d10plasma concentration-time curves in male Beagle dogs after subcutaneous administration of DMT-d10at 0.1, 0.5, and 1 mg / kg from Formulations 28-30, respectively, in linear scale (Fig.13A) and log scale (Fig.13B); 5 Fig.14 shows the dose proportionality of Cmax and AUCinf from the mean DMT-d10 plasma concentration-time curves in male Beagle dogs after subcutaneous administration of DMT-d10at 0.1, 0.5, and 1 mg / kg from Formulations 28-30, respectively; Fig.15 shows the effect of sodium hyaluronate concentration on mean concentration-time profiles of DMT-d10after SC administration of DMT-d10at a dose of 1 mg / kg from Formulations 10 30-33; *Formulation 31 dosed at 0.5 mg / kg free base was dose adjusted to 1 mg / kg; Fig. 16 shows the effect of sodium hyaluronate concentration on mean residence time (MRTinf) of DMT-d10after SC administration of DMT-d10at a dose of 1 mg / kg from Formulations 30-33; *Formulation 31 dosed at 0.5 mg / kg free base was dose adjusted to 1 mg / kg; Fig. 17 shows the effect of sodium hyaluronate concentration on plasma half-life (t1 / 2) of 15 DMT-d10 after SC administration of DMT-d10 at a dose of 1 mg / kg from Formulations 30-33; *Formulation 31 dosed at 0.5 mg / kg free base was dose adjusted to 1 mg / kg; Fig. 18 shows the effect of sodium hyaluronate concentration on maximum plasma concentration (Cmax) of DMT-d10 after SC administration of DMT-d10 at a dose of 1 mg / kg from Formulations 30-33; *Formulation 31 dosed at 0.5 mg / kg free base was dose adjusted to 1 mg / kg; 20 Fig. 19 shows the effect of sodium hyaluronate concentration on total exposure (AUCinf) of DMT-d10 after SC administration of DMT-d10 at a dose of 1 mg / kg from Formulations 30-33; *Formulation 31 dosed at 0.5 mg / kg free base was dose adjusted to 1 mg / kg; Figs.20A and 20B show mean DMT-d10plasma concentration-time curves in male Beagle dogs after subcutaneous administration of DMT-d10 at 1 mg / kg free base from Formulation 34 25 (dose solution concentration of 20 mg / mL nominal delivered at dosing volume of 0.05 mL / kg) compared to control (dose solution concentration of 4 mg / mL nominal delivered at dosing volume of 0.25 mL / kg) in linear scale (Fig.20A) and log scale (Fig.20B); Figs. 21A and 21B show mean DMT and DMT-d10 plasma concentration-time curves in male Beagle dogs after subcutaneous co-dose administration of DMT and DMT-d10at 0.5 30 mg / kg / analyte free base from Formulation 35 in linear scale (Fig.21A) and log scale (Fig.21B); and Fig.22 shows the percent drug release (ketamine) versus time profile of Formulations 36- 26

[0023] 38 compared to control when subjected to the Dialysis—Drug Release Test. DETAILED DESCRIPTION In the following detailed description of the embodiments of the instant disclosure, 5 numerous specific details are set forth in order to provide a thorough understanding of the disclosed embodiments. However, it will be obvious to one skilled in the art that the embodiments of this disclosure may be practiced without these specific details. In other instances, well known methods, procedures, components, and circuits have not been described in detail so as not to unnecessarily obscure aspects of the embodiments of the instant disclosure. 10 Definitions Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this disclosure belongs. “Alkyl” refers to monovalent saturated aliphatic hydrocarbyl groups having from 1 to 10 15 carbon atoms and such as 1 to 6 carbon atoms, or 1 to 5, or 1 to 4, or 1 to 3, or 1 to 2 carbon atoms. This term includes, by way of example, linear and branched hydrocarbyl groups such as methyl (CH3-), ethyl (CH3CH2-), n-propyl (CH3CH2CH2-), isopropyl ((CH3)2CH-), n-butyl (CH3CH2CH2CH2-), isobutyl ((CH3)2CHCH2-), sec-butyl ((CH3)(CH3CH2)CH-), t-butyl (t- Bu)((CH3)3C-), n-pentyl (CH3CH2CH2CH2CH2-), and neopentyl ((CH3)3CCH2-). 20 The term “substituted alkyl” refers to an alkyl group as defined herein wherein one or more carbon atoms in the alkyl chain have been optionally replaced with a heteroatom such as -O-, -N- , -S-, -S(O)n- (where n is 0 to 2), -NR- (where R is hydrogen or alkyl) and having from 1 to 10 substituents selected from the group consisting of deuterium, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, 25 acyloxy, amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, oxo, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, thioheterocyclooxy, thiol, thioalkoxy, substituted thioalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO-aryl, -SO-heteroaryl, -SO2- alkyl, -SO2-aryl, -SO2-heteroaryl, and -NR’R’’, wherein R’and R”may be the same or different 30 and are chosen from hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, heteroaryl and heterocyclic. “Alkylene” refers to divalent aliphatic hydrocarbyl groups having from 1 to 6, including, 27

[0024] for example, 1 to 3 carbon atoms that are either straight-chained or branched, and which are optionally interrupted with one or more groups selected from -O-, -NR10-, -NR10C(O), -C(O)NR10- and the like. This term includes, by way of example, methylene (-CH2-), ethylene (-CH2CH2-), n- propylene (-CH2CH2CH2-), iso-propylene (-CH2CH(CH3)-), (-C(CH3)2CH2CH2-), 5 (-C(CH3)2CH2C(O)-), (-C(CH3)2CH2C(O)NH-), (-CH(CH3)CH2-), and the like. “Substituted alkylene” refers to an alkylene group having from 1 to 3 hydrogens replaced with substituents as described for carbons in the definition of “substituted” below. The term “alkane” refers to alkyl group and alkylene group, as defined herein. The term “alkylaminoalkyl”, “alkylaminoalkenyl” and “alkylaminoalkynyl” refers to the 10 groups R’NHR”- where R’is alkyl group as defined herein and R”is alkylene, alkenylene or alkynylene group as defined herein. The term “alkaryl” or “aralkyl” refers to the groups -alkylene-aryl and -substituted alkylene-aryl where alkylene, substituted alkylene and aryl are defined herein. “Alkoxy” refers to the group –O-alkyl, wherein alkyl is as defined herein. Alkoxy includes,15 by way of example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, t-butoxy, sec-butoxy, n- pentoxy, and the like. The term “alkoxy” also refers to the groups alkenyl-O-, cycloalkyl-O-, cycloalkenyl-O-, and alkynyl-O-, where alkenyl, cycloalkyl, cycloalkenyl, and alkynyl are as defined herein. The term “substituted alkoxy” refers to the groups substituted alkyl-O-, substituted 20 alkenyl-O-, substituted cycloalkyl-O-, substituted cycloalkenyl-O-, and substituted alkynyl-O- where substituted alkyl, substituted alkenyl, substituted cycloalkyl, substituted cycloalkenyl and substituted alkynyl are as defined herein. The term “alkoxyamino” refers to the group –NH-alkoxy, wherein alkoxy is defined herein. The term “haloalkoxy” refers to the groups alkyl-O- wherein one or more hydrogen atoms 25 on the alkyl group have been substituted with a halo group and include, by way of examples, groups such as trifluoromethoxy, and the like. The term “haloalkyl” refers to a substituted alkyl group as described above, wherein one or more hydrogen atoms on the alkyl group have been substituted with a halo group. Examples of such groups include, without limitation, fluoroalkyl groups, such as trifluoromethyl, 30 difluoromethyl, trifluoroethyl and the like. The term “alkylalkoxy” refers to the groups -alkylene-O-alkyl, alkylene-O-substituted alkyl, substituted alkylene-O-alkyl, and substituted alkylene-O-substituted alkyl wherein alkyl, 28

[0025] substituted alkyl, alkylene and substituted alkylene are as defined herein. The term “alkylthioalkoxy” refers to the group -alkylene-S-alkyl, alkylene-S-substituted alkyl, substituted alkylene-S-alkyl and substituted alkylene-S-substituted alkyl wherein alkyl, substituted alkyl, alkylene and substituted alkylene are as defined herein. 5 “Alkenyl” refers to straight chain or branched hydrocarbyl groups having from 2 to 6 carbon atoms, for example 2 to 4 carbon atoms and having at least 1, for example from 1 to 2 sites of double bond unsaturation. This term includes, by way of example, bi-vinyl, allyl, and but-3-en-1-yl. Included within this term are the cis and trans isomers or mixtures of these isomers. The term “substituted alkenyl” refers to an alkenyl group as defined herein having from 1 10 to 5 substituents, or from 1 to 3 substituents, selected from deuterium, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, acyloxy, amino, substituted amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, oxo, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, thioheterocyclooxy, thiol, thioalkoxy, substituted thioalkoxy, aryl, aryloxy, heteroaryl,15 heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO- substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2-substituted alkyl, -SO2-aryl and - SO2-heteroaryl. “Alkynyl” refers to straight or branched monovalent hydrocarbyl groups having from 2 to 6 carbon atoms, for example, 2 to 3 carbon atoms and having at least 1 and for example, from 1 to 20 2 sites of triple bond unsaturation. Examples of such alkynyl groups include acetylenyl (-C≡CH), and propargyl (-CH2C≡CH). The term “substituted alkynyl” refers to an alkynyl group as defined herein having from 1 to 5 substituents, or from 1 to 3 substituents, selected from deuterium, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, 25 acyloxy, amino, substituted amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, oxo, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, thioheterocyclooxy, thiol, thioalkoxy, substituted thioalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO- substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2-substituted alkyl, -SO2-aryl, and - 30 SO2-heteroaryl. “Alkynyloxy” refers to the group –O-alkynyl, wherein alkynyl is as defined herein. Alkynyloxy includes, by way of example, ethynyloxy, propynyloxy, and the like. 29

[0026] “Acyl” refers to the groups H-C(O)-, alkyl-C(O)-, substituted alkyl-C(O)-, alkenyl-C(O)-, substituted alkenyl-C(O)-, alkynyl-C(O)-, substituted alkynyl-C(O)-, cycloalkyl-C(O)-, substituted cycloalkyl-C(O)-, cycloalkenyl-C(O)-, substituted cycloalkenyl-C(O)-, aryl-C(O)-, substituted aryl-C(O)-, heteroaryl-C(O)-, substituted heteroaryl-C(O)-, heterocyclyl-C(O)-, and 5 substituted heterocyclyl-C(O)-, wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. For example, acyl includes the “acetyl” group CH3C(O) “Acylamino” refers to the groups –NR20C(O)alkyl, -NR20C(O)substituted alkyl, N10 R20C(O)cycloalkyl, -NR20C(O)substituted cycloalkyl, - NR20C(O)cycloalkenyl, -NR20C(O)substituted cycloalkenyl, -NR20C(O)alkenyl, - NR20C(O)substituted alkenyl, -NR20C(O)alkynyl, -NR20C(O)substituted alkynyl, -NR20C(O)aryl, -NR20C(O)substituted aryl, -NR20C(O)heteroaryl, -NR20C(O)substituted heteroaryl, -NR20C(O)heterocyclic, and -NR20C(O)substituted heterocyclic, wherein R20is 15 hydrogen or alkyl and wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. “Aminocarbonyl” or the term “aminoacyl” refers to the group -C(O)NR21R22, wherein R2120 and R22independently are selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic and where R21and R22are optionally joined together with the nitrogen bound thereto to form a heterocyclic or substituted heterocyclic group, and 25 wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. “Aminocarbonylamino” refers to the group –NR21C(O)NR22R23where R21, R22, and R23are independently selected from hydrogen, alkyl, aryl or cycloalkyl, or where two R groups are 30 joined to form a heterocyclyl group. The term “alkoxycarbonylamino” refers to the group -NRC(O)OR where each R is independently hydrogen, alkyl, substituted alkyl, aryl, heteroaryl, or heterocyclyl wherein alkyl, 30

[0027] substituted alkyl, aryl, heteroaryl, and heterocyclyl are as defined herein. The term “acyloxy” refers to the groups alkyl-C(O)O-, substituted alkyl-C(O)O-, cycloalkyl-C(O)O-, substituted cycloalkyl-C(O)O-, aryl-C(O)O-, heteroaryl-C(O)O-, and heterocyclyl-C(O)O- wherein alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, aryl, 5 heteroaryl, and heterocyclyl are as defined herein. “Aminosulfonyl” refers to the group –SO2NR21R22, wherein R21and R22independently are selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heteroaryl, substituted heteroaryl, heterocyclic, substituted 10 heterocyclic and where R21and R22are optionally joined together with the nitrogen bound thereto to form a heterocyclic or substituted heterocyclic group and alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic and substituted heterocyclic are as defined herein. 15 “Sulfonylamino” refers to the group –NR21SO2R22, wherein R21and R22independently are selected from the group consisting of hydrogen, alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, aryl, substituted aryl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic and where R21and R22are optionally joined together with the atoms bound 20 thereto to form a heterocyclic or substituted heterocyclic group, and wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. “Aryl” or “Ar” refers to a monovalent aromatic carbocyclic group of from 6 to 18 carbon 25 atoms having a single ring (such as is present in a phenyl group) or a ring system having multiple condensed rings (examples of such aromatic ring systems include naphthyl, anthryl and indanyl) which condensed rings may or may not be aromatic, provided that the point of attachment is through an atom of an aromatic ring. This term includes, by way of example, phenyl and naphthyl. Unless otherwise constrained by the definition for the aryl substituent, such aryl groups can 30 optionally be substituted with from 1 to 5 substituents, or from 1 to 3 substituents, selected from acyloxy, hydroxy, thiol, acyl, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, substituted alkyl, substituted alkoxy, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, 31

[0028] substituted cycloalkenyl, amino, substituted amino, aminoacyl, acylamino, alkaryl, aryl, aryloxy, azido, carboxyl, carboxylalkyl, cyano, halogen, nitro, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, aminoacyloxy, oxyacylamino, thioalkoxy, substituted thioalkoxy, thioaryloxy, thioheteroaryloxy, -SO-alkyl, -SO-substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2- 5 substituted alkyl, -SO2-aryl, -SO2-heteroaryl and trihalomethyl. “Aryloxy” refers to the group –O-aryl, wherein aryl is as defined herein, including, by way of example, phenoxy, naphthoxy, and the like, including optionally substituted aryl groups as also defined herein. “Amino” refers to the group –NH2. 10 The term “substituted amino” refers to the group -NRR where each R is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, alkenyl, substituted alkenyl, cycloalkenyl, substituted cycloalkenyl, alkynyl, substituted alkynyl, aryl, heteroaryl, and heterocyclyl provided that at least one R is not hydrogen. The term “azido” refers to the group –N3. 15 “Carboxyl,” “carboxy” or “carboxylate” refers to –CO2H or salts thereof. “Carboxyl ester” or “carboxy ester” or the terms “carboxyalkyl” or “carboxylalkyl” refers to the groups -C(O)O-alkyl, -C(O)O-substituted alkyl, -C(O)O-alkenyl, -C(O)O-substituted alkenyl, -C(O)O-alkynyl, -C(O)O-substituted alkynyl, -C(O)O-aryl, -C(O)O-substituted aryl, -C(O)O-cycloalkyl, -C(O)O-substituted 20 cycloalkyl, -C(O)O-cycloalkenyl, -C(O)O-substituted cycloalkenyl, -C(O)O-heteroaryl, -C(O)O-substituted heteroaryl, -C(O)O-heterocyclic, and -C(O)O-substituted heterocyclic, wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted 25 heterocyclic are as defined herein. “(Carboxyl ester)oxy” or “carbonate” refers to the groups –O-C(O)O- alkyl, -O-C(O)O-substituted alkyl, -O-C(O)O-alkenyl, -O-C(O)O-substituted alkenyl, -O-C(O)O- alkynyl, -O-C(O)O-substituted alkynyl, -O-C(O)O-aryl, -O-C(O)O-substituted aryl, -O-C(O)O- cycloalkyl, -O-C(O)O-substituted cycloalkyl, -O-C(O)O-cycloalkenyl, -O-C(O)O-substituted 30 cycloalkenyl, -O-C(O)O-heteroaryl, -O-C(O)O-substituted heteroaryl, -O-C(O)O-heterocyclic, and -O-C(O)O-substituted heterocyclic, wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted 32

[0029] cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. “Cyano” or “nitrile” refers to the group –CN. “Cycloalkyl” refers to cyclic alkyl groups of from 3 to 10 carbon atoms having single or 5 multiple cyclic rings including fused, bridged, and spiro ring systems. Examples of suitable cycloalkyl groups include, for instance, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like. Such cycloalkyl groups include, by way of example, single ring structures such as cyclopropyl, cyclobutyl, cyclopentyl, cyclooctyl, and the like, or multiple ring structures such as adamantanyl, and the like. 10 The term “substituted cycloalkyl” refers to cycloalkyl groups having from 1 to 5 substituents, or from 1 to 3 substituents, selected from deuterium, alkyl, substituted alkyl, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, acyloxy, amino, substituted amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, oxo, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, 15 thioheterocyclooxy, thiol, thioalkoxy, substituted thioalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO- substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2-substituted alkyl, -SO2-aryl and - SO2-heteroaryl. “Cycloalkenyl” refers to non-aromatic cyclic alkyl groups of from 3 to 10 carbon atoms 20 having single or multiple rings and having at least one double bond and for example, from 1 to 2 double bonds. The term “substituted cycloalkenyl” refers to cycloalkenyl groups having from 1 to 5 substituents, or from 1 to 3 substituents, selected from deuterium, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, 25 acyloxy, amino, substituted amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, keto, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, thioheterocyclooxy, thiol, thioalkoxy, substituted thioalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO- substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2-substituted alkyl, -SO2-aryl and - 30 SO2-heteroaryl. “Cycloalkynyl” refers to non-aromatic cycloalkyl groups of from 5 to 10 carbon atoms having single or multiple rings and having at least one triple bond. 33

[0030] “Cycloalkoxy” refers to –O-cycloalkyl. “Cycloalkenyloxy” refers to –O-cycloalkenyl. “Halo” or “halogen” refers to fluoro, chloro, bromo, and iodo. “Hydroxy” or “hydroxyl” refers to the group –OH. 5 “Heteroaryl” refers to an aromatic group of from 1 to 15 carbon atoms, such as from 1 to 10 carbon atoms and 1 to 10 heteroatoms selected from the group consisting of oxygen, nitrogen, and sulfur within the ring. Such heteroaryl groups can have a single ring (such as, pyridinyl, imidazolyl or furyl) or multiple condensed rings in a ring system (for example as in groups such as, indolizinyl, quinolinyl, benzofuran, benzimidazolyl or benzothienyl), wherein at least one ring 10 within the ring system is aromatic and at least one ring within the ring system is aromatic, provided that the point of attachment is through an atom of an aromatic ring. In certain embodiments, the nitrogen and / or sulfur ring atom(s) of the heteroaryl group are optionally oxidized to provide for the N-oxide (N→O), sulfinyl, or sulfonyl moieties. This term includes, by way of example, pyridinyl, pyrrolyl, indolyl, thiophenyl, and furanyl. Unless otherwise constrained by the 15 definition for the heteroaryl substituent, such heteroaryl groups can be optionally substituted with 1 to 5 substituents, or from 1 to 3 substituents, selected from acyloxy, hydroxy, thiol, acyl, alkyl, alkoxy, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, substituted alkyl, substituted alkoxy, substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted cycloalkenyl, amino, substituted amino, aminoacyl, acylamino, alkaryl, aryl, aryloxy, azido, carboxyl, carboxylalkyl, 20 cyano, halogen, nitro, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, aminoacyloxy, oxyacylamino, thioalkoxy, substituted thioalkoxy, thioaryloxy, thioheteroaryloxy, -SO-alkyl, - SO-substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2-substituted alkyl, -SO2-aryl and -SO2-heteroaryl, and trihalomethyl. The term “heteroaralkyl” refers to the groups -alkylene-heteroaryl where alkylene and 25 heteroaryl are defined herein. This term includes, by way of example, pyridylmethyl, pyridylethyl, indolylmethyl, and the like. “Heteroaryloxy” refers to –O-heteroaryl. “Heterocycle,” “heterocyclic,” “heterocycloalkyl,” and “heterocyclyl” refer to a saturated or unsaturated group having a single ring or multiple condensed rings, including fused bridged and 30 spiro ring systems, and having from 3 to 20 ring atoms, including 1 to 10 hetero atoms. These ring atoms are selected from the group consisting of nitrogen, sulfur, or oxygen, wherein, in fused ring systems, one or more of the rings can be cycloalkyl, aryl, or heteroaryl, provided that the point of 34

[0031] attachment is through the non-aromatic ring. In certain embodiments, the nitrogen and / or sulfur atom(s) of the heterocyclic group are optionally oxidized to provide for the N-oxide, -S(O)-, or – SO2- moieties. Examples of heterocycles and heteroaryls include, but are not limited to, azetidine, pyrrole, 5 imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, indolizine, isoindole, indole, dihydroindole, indazole, purine, quinolizine, isoquinoline, quinoline, phthalazine, naphthylpyridine, quinoxaline, quinazoline, cinnoline, pteridine, carbazole, carboline, phenanthridine, acridine, phenanthroline, isothiazole, phenazine, isoxazole, phenoxazine, phenothiazine, imidazolidine, imidazoline, piperidine, piperazine, indoline, phthalimide, 1,2,3,4- 10 tetrahydroisoquinoline, 4,5,6,7-tetrahydrobenzo[b]thiophene, thiazole, thiazolidine, thiophene, benzo[b]thiophene, morpholinyl, thiomorpholinyl (also referred to as thiamorpholinyl), 1,1- dioxothiomorpholinyl, piperidinyl, pyrrolidine, tetrahydrofuranyl, benzo[d][1,3]oxathiole, benzo[d][1,3]dioxole, and the like. Unless otherwise constrained by the definition for the heterocyclic substituent, such 15 heterocyclic groups can be optionally substituted with 1 to 5, or from 1 to 3 substituents, selected from deuterium, alkoxy, substituted alkoxy, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, acyl, acylamino, acyloxy, amino, substituted amino, aminoacyl, aminoacyloxy, oxyaminoacyl, azido, cyano, halogen, hydroxyl, oxo, thioketo, carboxyl, carboxylalkyl, thioaryloxy, thioheteroaryloxy, thioheterocyclooxy, thiol, thioalkoxy, substituted 20 thioalkoxy, aryl, aryloxy, heteroaryl, heteroaryloxy, heterocyclyl, heterocyclooxy, hydroxyamino, alkoxyamino, nitro, -SO-alkyl, -SO-substituted alkyl, -SO-aryl, -SO-heteroaryl, -SO2-alkyl, -SO2- substituted alkyl, -SO2-aryl, -SO2-heteroaryl, and fused heterocycle. “Heterocyclyloxy” refers to the group –O-heterocyclyl. The term “heterocyclylthio” refers to the group heterocyclic-S-. 25 The term “heterocyclene” refers to the diradical group formed from a heterocycle, as defined herein. The term “hydroxyamino” refers to the group -NHOH. “Nitro” refers to the group –NO2. “Oxo” refers to the atom (=O). 30 “Sulfonyl” refers to the group SO2-alkyl, SO2-substituted alkyl, SO2-alkenyl, SO2- substituted alkenyl, SO2-cycloalkyl, SO2-substituted cylcoalkyl, SO2-cycloalkenyl, SO2- substituted cylcoalkenyl, SO2-aryl, SO2-substituted aryl, SO2-heteroaryl, SO2-substituted35

[0032] heteroaryl, SO2-heterocyclic, and SO2-substituted heterocyclic, wherein alkyl, substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. Sulfonyl includes, by way of 5 example, methyl-SO2-, phenyl-SO2-, and 4-methylphenyl-SO2-. “Sulfonyloxy” refers to the group –OSO2-alkyl, OSO2-substituted alkyl, OSO2-alkenyl, OSO2-substituted alkenyl, OSO2-cycloalkyl, OSO2-substituted cylcoalkyl, OSO2-cycloalkenyl, OSO2-substituted cylcoalkenyl, OSO2-aryl, OSO2-substituted aryl, OSO2-heteroaryl, OSO2- substituted heteroaryl, OSO2-heterocyclic, and OSO2substituted heterocyclic, wherein alkyl, 10 substituted alkyl, alkenyl, substituted alkenyl, alkynyl, substituted alkynyl, cycloalkyl, substituted cycloalkyl, cycloalkenyl, substituted cycloalkenyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclic, and substituted heterocyclic are as defined herein. The term “aminocarbonyloxy” refers to the group -OC(O)NRR where each R is independently hydrogen, alkyl, substituted alkyl, aryl, heteroaryl, or heterocyclic wherein alkyl, 15 substituted alkyl, aryl, heteroaryl and heterocyclic are as defined herein. “Thiol” refers to the group -SH. “Thioxo” or the term “thioketo” refers to the atom (=S). “Alkylthio” or the term “thioalkoxy” refers to the group -S-alkyl, wherein alkyl is as defined herein. In certain embodiments, sulfur may be oxidized to -S(O)-. The sulfoxide may exist 20 as one or more stereoisomers. The term “substituted thioalkoxy” refers to the group -S-substituted alkyl. The term “thioaryloxy” refers to the group aryl-S- wherein the aryl group is as defined herein including optionally substituted aryl groups also defined herein. The term “thioheteroaryloxy” refers to the group heteroaryl-S- wherein the heteroaryl 25 group is as defined herein including optionally substituted aryl groups as also defined herein. The term “thioheterocyclooxy” refers to the group heterocyclyl-S- wherein the heterocyclyl group is as defined herein including optionally substituted heterocyclyl groups as also defined herein. In addition to the disclosure herein, the term “substituted,” when used to modify a specified 30 group or radical, can also mean that one or more hydrogen atoms of the specified group or radical are each, independently of one another, replaced with the same or different substituent groups as defined below. 36

[0033] In addition to the groups disclosed with respect to the individual terms herein, substituent groups for substituting for one or more hydrogens (any two hydrogens on a single carbon can be replaced with =O, =NR70, =N-OR70, =N2or =S) on saturated carbon atoms in the specified group or radical are, unless otherwise specified, deuterium, -R60, halo, =O, -OR70, -SR70, -NR80R80, 5 trihalomethyl, -CN, -OCN, -SCN, -NO, -NO2, =N2, -N3, -SO2R70, -SO2O–M+, -SO2OR70, -OSO2R70, -OSO2O–M+, -OSO2OR70, -P(O)(O–)2(M+)2, -P(O)(OR70)O–M+, -P(O)(OR70)2, -C(O)R70, -C(S)R70, -C(NR70)R70, -C(O)O–M+, -C(O)OR70, -C(S)OR70, -C(O)NR80R80, -C(NR70)NR80R80, -OC(O)R70, -OC(S)R70, -OC(O)O-M+, -OC(O)OR70, -OC(S)OR70, -NR70C(O)R70, -NR70C(S)R70, 10 -NR70CO2–M+, -NR70CO2R70, -NR70C(S)OR70, -NR70C(O)NR80R80, -NR70C(NR70)R70and -NR70C(NR70)NR80R80, where R60is selected from the group consisting of optionally substituted alkyl, cycloalkyl, heteroalkyl, heterocycloalkylalkyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl and heteroarylalkyl, each R70is independently hydrogen or R60; each R80is independently R70or alternatively, two R80’s, taken together with the nitrogen atom to which they 15 are bonded, form a 5-, 6- or 7-membered heterocycloalkyl which may optionally include from 1 to 4 of the same or different additional heteroatoms selected from the group consisting of O, N and S, of which N may have -H or C1-C3 alkyl substitution; and each M+is a counter ion with a net single positive charge. Each M+may independently be, for example, an alkali ion, such as K+, Na+, Li+; an ammonium ion, such as+N(R60)4; or an alkaline earth ion, such as [Ca2+]0.5, [Mg2+]0.5, or 20 [Ba2+]0.5(“subscript 0.5 means that one of the counter ions for such divalent alkali earth ions can be an ionized form of a compound of the disclosure and the other a typical counter ion such as chloride, or two ionized compounds disclosed herein can serve as counter ions for such divalent alkali earth ions, or a doubly ionized compound of the disclosure can serve as the counter ion for such divalent alkali earth ions). As specific examples, -NR80R80is meant to25 include -NH2, -NH-alkyl, N-pyrrolidinyl, N-piperazinyl, 4N-methyl-piperazin-1-yl and N- morpholinyl. In addition to the disclosure herein, substituent groups for hydrogens on unsaturated carbon atoms in “substituted” alkene, alkyne, aryl and heteroaryl groups are, unless otherwise specified, deuterium, -R60, halo, -O-M+, -OR70, -SR70, -S–M+, -NR80R80, 30 trihalomethyl, -CF3, -CN, -OCN, -SCN, -NO, -NO2, -N3, -SO2R70, -SO3–M+, -SO3R70, -OSO2R70, -OSO3–M+, -OSO3R70, -PO3-2(M+)2, -P(O)(OR70)O–M+, -P(O)(OR70)2, -C(O)R70, -C(S)R70, -C(NR70)R70, 37

[0034] -CO2–M+, -CO2R70, -C(S)OR70, -C(O)NR80R80, -C(NR70)NR80R80, -OC(O)R70, -OC(S)R70, -OCO2–M+, -OCO2R70, -OC(S)OR70, -NR70C(O)R70, -NR70C(S)R70, -NR70CO2–M+, -NR70CO2R70, -NR70C(S)OR70, -NR70C(O)NR80R80, -NR70C(NR70)R70and -NR70C(NR70)NR80R80, where R60, R70, R80and M+are as previously defined, provided that 5 in case of substituted alkene or alkyne, the substituents are not -O-M+, -OR70, -SR70, or -S–M+. In addition to the groups disclosed with respect to the individual terms herein, substituent groups for hydrogens on nitrogen atoms in “substituted” heteroalkyl and cycloheteroalkyl groups are, unless otherwise specified, -R60, -O-M+, -OR70, -SR70, -S-M+, -NR80R80, trihalomethyl, -CF3, -CN, -NO, -NO2, -S(O)2R70, -S(O)2O-M+, -S(O)2OR70, -OS(O)2R70, -OS(O)210 O-M+, -OS(O)2OR70, -P(O)(O-)2(M+)2, -P(O)(OR70)O-M+, -P(O)(OR70)(OR70), -C(O)R70, -C(S)R70, -C(NR70)R70, -C(O)OR70, -C(S)OR70, -C(O)NR80R80, -C(NR70)NR80R80, -OC(O)R70, -OC(S)R70, -OC(O)OR70, -OC(S)OR70, -NR70C(O)R70, -NR70C(S)R70, -NR70C(O)OR70, -NR70C(S)OR70, -NR70C(O)NR80R80, -NR70C(NR70)R70and -NR70C(NR70)NR80R80, where R60, R70, R80and M+are as previously defined. 15 In addition to the disclosure herein, in some embodiments, a group that is substituted has 1, 2, 3, or 4 substituents, 1, 2, or 3 substituents, 1 or 2 substituents, or 1 substituent. It is understood that in all substituted groups defined above, polymers arrived at by defining substituents with further substituents to themselves (e.g., substituted aryl having a substituted aryl group as a substituent which is itself substituted with a substituted aryl group, which is further 20 substituted by a substituted aryl group, etc.) are not intended for inclusion herein, unless specified otherwise. In such cases, the maximum number of such substitutions is three. For example, serial substitutions of substituted aryl groups specifically contemplated herein are limited to substituted aryl-(substituted aryl)-substituted aryl. However, substituent groups defined as e.g., polyethers may contain serial substitution greater than three, e.g., -O-(CH2CH2O)n-H, where n can be 1, 2, 3, 25 or greater. Unless indicated otherwise, the nomenclature of substituents that are not explicitly defined herein are arrived at by naming the terminal portion of the functionality followed by the adjacent functionality toward the point of attachment. For example, the substituent “arylalkyloxycarbonyl” refers to the group (aryl)-(alkyl)-O-C(O)-. 30 As to any of the groups disclosed herein which contain one or more substituents, it is understood, of course, that such groups do not contain any substitution or substitution patterns which are sterically impractical and / or synthetically non-feasible. In addition, the subject 38

[0035] compounds include all stereochemical isomers arising from the substitution of these compounds. When it is stated that a substituent or group “comprise(s) deuterium” or is “comprising deuterium,” it is to be understood that the substituent or group may itself be deuterium, or the substituent or group may contain at least one deuterium substitution in its chemical structure. For 5 example, when substituent “-R” is defined to comprise deuterium, it is to be understood that -R may be -D (-deuterium), or a group such as -CD3that is consistent with the other requirements set forth of -R. As used herein, the term “fatty” describes a compound with a long-chain (linear) hydrophobic portion made up of hydrogen and anywhere from 4 to 26 carbon atoms, which may 10 be fully saturated or partially unsaturated. The phrases “pharmaceutically acceptable,” “physiologically acceptable,” and the like, are employed herein to refer to those compounds, materials, compositions, and / or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings without excessive toxicity, irritation, allergic response, or other problem or 15 complication, commensurate with a reasonable benefit / risk ratio. When referencing salts, the phrase “pharmaceutically acceptable salt” and the like, means a salt which is acceptable for administration to a patient, such as a mammal (salts with counterions having acceptable mammalian safety for a given dosage regime). As is well known in the art, such salts can be derived from pharmaceutically acceptable inorganic or organic bases, by way of example, sodium, 20 potassium, calcium, magnesium, ammonium, and tetraalkylammonium salts, and the like, and when the molecule contains a basic functionality, addition salts with inorganic acids, such as hydrochloride, hydrobromide, sulfate, sulfamate, phosphate, nitrate, perchlorate salts, and the like, and addition salts with organic acids, such as formate, tartrate, besylate, mesylate, acetate, maleate, oxalate, fumarate, benzoate, salicylate, succinate, oxalate, glycolate, hemi-oxalate, hemi-fumarate, 25 propionate, stearate, lactate, citrate, ascorbate, pamoate, hydroxymaleate, phenylacetate, glutamate, 2-acetoxybenzoate, tosylate, ethanedisulfonate, isethionate salts, and the like. When in the form of a solid, salts designated as “hemi-” salts indicate that the stoichiometry of subject compound to counterion is about 2:1, whereas solid salt forms without the “hemi-” descriptor possess a subject compound to counterion stoichiometry of about 1:1. For example, DMT hemi- 30 fumarate indicates that the ratio of DMT to fumarate is 2:1, whereas DMT fumarate indicates that the ratio of DMT to fumarate is 1:1. 39

[0036] “Solvate” refers to a physical association of a compound or salt of the present disclosure with one or more solvent molecules, whether organic, inorganic, or a mixture of both. This physical association includes hydrogen bonding. In certain instances, the solvate will be capable of isolation, for example when one or more solvent molecules are incorporated in the crystal lattice 5 of the crystalline solid. The solvent molecules in the solvate may be present in a regular arrangement and / or a non-ordered arrangement. The solvate may comprise either a stoichiometric or nonstoichiometric amount of the solvent molecules. “Solvate” encompasses both solution-phase and isolable solvates. Some examples of solvents include, but are not limited to, methanol, ethanol, isopropanol, N,N-dimethylformamide, tetrahydrofuran, dimethylsulfoxide, and water. When the 10 solvent is water, the solvate formed is a hydrate (e.g., monohydrate, dihydrate, etc.). Exemplary solvates thus include, but are not limited to, hydrates, methanolates, ethanolates, isopropanolates, etc. Methods of solvation are generally known in the art. “Stereoisomer” and “stereoisomers” refer to compounds that have same atomic connectivity but different atomic arrangement in space. Stereoisomers include cis-trans isomers, 15 E and Z isomers, enantiomers, and diastereomers. All forms such as racemates and optically pure stereoisomers of the compounds are contemplated herein. Chemical formulas and compounds which possess at least one stereogenic center, but are drawn without reference to stereochemistry, are intended to encompass both the racemic compound, as well as the separate stereoisomers, e.g., R- and / or S-stereoisomers, each permutation of diastereomers so long as those diastereomers are 20 geometrically feasible, etc. A “crystalline” solid is a type of solid whose fundamental three-dimensional structure contains a highly regular pattern of atoms or molecules—with long range order—forming a crystal lattice, and thus displays sharp characteristic crystalline peak(s) in its X-ray power diffraction (XRPD) pattern. In some instances, crystalline solids can exist in different crystalline forms 25 known as “polymorphs,” which have the same chemical composition, but differ in packing, geometric arrangement, and other descriptive properties of the crystalline solid state. As such, polymorphs may have different solid-state physical properties to affect, for example, the solubility, dissolution rate, bioavailability, chemical and physical stability, flowability, and compressibility, etc. of the compound as well as the safety and efficacy of drug products based on the compound. 30 In the process of preparing a polymorph, further purification, in terms of gross physical purity or optical purity, may be accomplished as well. As used herein, the term “amorphous” refers to a solid material having substantially no long range order in the position of its molecules—the 40

[0037] molecules are arranged in a random manner so that there is effectively no well-defined arrangement, e.g., molecular packing, and no long range order. Amorphous solids are generally isotropic, i.e., exhibit similar properties in all directions and do not have definite melting points. For example, an amorphous material is a solid material having substantially no sharp characteristic 5 crystalline peak(s) in its X-ray power diffraction (XRPD) pattern (i.e., is not crystalline as determined by XRPD). Instead, one or several broad peaks (e.g., halos) appear in its XRPD pattern. Broad peaks are characteristic of an amorphous solid. Thus, an “amorphous” subject compound / material is one characterized as having substantially no crystallinity—less than 10% crystallinity, less than 8% crystallinity, less than 6% crystallinity, less than 4% crystallinity, less 10 than 2% crystallinity, less than 1% crystallinity, or 0% crystallinity—i.e., is at least 90%, at least 92%, at least 94%, at least 96%, at least 98%, or 100% amorphous, as determined for example by XRPD. For example, the % crystallinity can in some embodiments be determined by measuring the intensity of one or more peaks in the XRPD diffractogram compared to a reference peak, which may be that of a known standard or an internal standard. Other characterization techniques, such 15 as differential scanning calorimetry (DSC) analysis, Fourier transform infrared spectroscopy (FTIR), and other quantitative methods, may also be employed to determine the percent a subject compound / material is amorphous or crystalline, including quantitative methods which provide the above percentages in terms of weight percent. When referencing X-ray powder diffraction (XRPD) patterns of materials of the present 20 disclosure, the phrase “characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from…” should be understood to include those materials characterized as having 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 or more (including all) of the recited characteristic XRPD diffraction peaks. Further, this phrase is intended to be open to the inclusion of other XRPD diffraction peaks not recited. 25 It will be appreciated that the compounds herein can exist in different salt, solvate, stereoisomer, crystalline / amorphous (including polymorphic) forms, and the present disclosure is intended to include all permutations thereof, such as a solvate of a pharmaceutically acceptable salt of a stereoisomer of the subject compound. The language “tamper resistant” is art-recognized to describe aspects of a drug formulation 30 that make it more difficult to use the formulation to abuse the drug moiety of the formulation through e.g., extraction for intravenous use, or crushing for freebase use; and therefore, reduce the risk for abuse of the drug. 41

[0038] The term “stable,” “stability,” and the like, as used herein includes chemical stability and solid state (physical) stability. The term “chemical stability” means that the compound can be stored in an isolated form, or in the form of a formulation in which it is provided in admixture with for example, pharmaceutically acceptable carriers, diluents or adjuvants as described herein, under 5 normal storage conditions, with little or no chemical degradation or decomposition. “Solid-state stability” means the compound can be stored in an isolated solid form, or the form of a solid formulation in which it is provided in admixture with, for example, pharmaceutically acceptable carriers, diluents or adjuvants as described herein, under normal storage conditions, with little or no solid-state transformation (e.g., hydration, dehydration, solvatization, desolvatization, 10 crystallization, recrystallization or solid-state phase transition). As used herein, the term “composition” is equivalent to the term “formulation.” The term “treating” or “treatment” as used herein means the treating or treatment of a disease or medical condition in a patient, such as a mammal (particularly a human) that includes: ameliorating the disease or medical condition, such as, eliminating or causing regression of the 15 disease or medical condition in a patient; suppressing the disease or medical condition, for example by, slowing or arresting the development of the disease or medical condition in a patient; or alleviating one or more symptoms of the disease or medical condition in a patient. A treatment can provide a therapeutic benefit such as the eradication or amelioration of one or more of the physiological or psychological symptoms associated with the underlying condition, disease, or 20 disorder such that an improvement is observed in the patient, notwithstanding the fact that the patient may still be affected by the condition. In some embodiments, treatment may refer to prophylaxis, i.e., preventing the disease or medical condition from occurring or otherwise delaying the onset of the disease or medical condition in a patient. A “patient” or “subject,” used interchangeably herein, can be any mammal including, for 25 example, a human. A patient or subject can have a condition to be treated or can be susceptible to a condition to be treated. A “psychopharmaceutical agent” is a chemical substance with the ability to cross the blood-brain barrier and act on the nervous system, resulting in alterations in perception, mood, consciousness, cognition, and / or behavior. Categories of psychopharmaceutical agents include 30 anxiolytics (e.g., benzodiazepines, barbiturates, etc.), empathogen-entactogens (e.g., MDMA, MDA, AMT, etc.), stimulants (e.g., amphetamines, modafinil, etc.), depressants (e.g., sedatives, 42

[0039] hypnotics, and opioids), and hallucinogens such as psychedelics, dissociatives, and deliriants (e.g., psilocybin, LSD, DMT, mescaline, salvia divinorum, scopolamine, etc.). As used herein, and unless otherwise specified, the terms “manage,” “managing” and “management” refer to preventing or slowing the progression, spread or worsening of a disease, 5 disorder, or condition, or of one or more symptoms thereof. Often, the beneficial effects that a subject derives from a prophylactic and / or therapeutic agent do not result in a cure of the disease, disorder, or condition. In this regard, the term “managing” encompasses treating a subject who had suffered from the particular disease, disorder, or condition in an attempt to prevent or minimize the recurrence of the disease, disorder, or condition, or of one or more symptoms thereof. 10 “Therapeutically effective amount” refers to an amount of a compound(s) or its salt form sufficient to treat a specified disorder or disease or one or more of its symptoms and / or to prevent the occurrence of the disease or disorder (prophylactically effective amount). As used herein, and unless otherwise specified, a “prophylactically effective amount” of an active agent, is an amount sufficient to prevent a disease, disorder, or condition, or prevent its recurrence. The term 15 “prophylactically effective amount” can encompass an amount that improves overall prophylaxis or enhances the prophylactic efficacy of another prophylactic agent. The term “administration schedule” is a plan in which the type, amount, period, procedure, etc. of the drug in the drug treatment are shown in time series, and the dosage, administration method, administration order, administration date, and the like of each drug are indicated. The date 20 specified to be administered is determined before the start of the drug administration. The administration is continued by repeating the course with the set of administration schedules as “courses”. A “continuous” administration schedule means administration every day without interruption during the treatment course. If the administration schedule follows an “intermittent” administration schedule, then days of administration may be followed by “rest days” or days of 25 non-administration of drug within the course. A “drug holiday” indicates that the drug is not administered in a predetermined administration schedule. For example, after undergoing several courses of treatment, a subject may be prescribed a regulated drug holiday as part of the administration schedule, e.g., prior to re-recommencing active treatment. As used herein, a “bolus” is where a discrete amount of active pharmaceutical ingredient 30 (API) (e.g., a psychopharmaceutical agent) is administered (e.g., by injection) within 30 minutes or less such that the concentration of the API in the body quickly increases. Bolus injections are typically administered intravenously (directly into the vein), intramuscularly (within the muscle), 43

[0040] intradermally (beneath the skin), or subcutaneously (within the fat or skin). A bolus injection thus differs from an “infusion,” whereby a discrete amount of API (e.g., a psychopharmaceutical agent) is administered by single injection or multiple injections over a prolonged period of greater than 30 minutes, such that the concentration of the API in the body follows a more stable kinetic profile, 5 in some cases reaching a steady-state, with a prolonged exposure period. The language “toxic spikes” is used herein to describe spikes in concentration of any compound described herein that would produce side-effects of sedation or psychotomimetic effects, e.g., hallucination, dizziness, and nausea; which can not only have immediate repercussions, but also influence treatment compliance. In particular, side effects may become 10 more pronounced at blood concentration levels above about 300 ng / mL (e.g. above about 300, 400, 500, 600 or more ng / mL). According to IUPAC, “osmolality” is the quotient of the negative natural logarithm of the rational activity of water and the molar mass of water. In simpler terms, osmolality is an expression of the number of osmotically active particles (the number of solute particles) in 1 kg of a solution, 15 represented herein as the number of milliosmoles (mOsm) per 1 kg of solution. Thus, osmolality is a function only of the number of particles, and is not related to particle molecular weight, size, shape, or charge (see D. K. Faria et al., M. E. Mendes and N. M. Sumita, J. Bras. Pata!. Med. Lab., 53, 1, 38-45 (2017) for a review of the measurement of serum osmolality). For example, one mole of a nondissociating substance (e.g., glucose) dissolved in 1 kg of water has an osmolality of 1 20 Osm / kg (1000 mOsm / kg), whilst one mole of a substance that dissociates into two separate species in solution (e.g., sodium chloride) dissolved in 1 kg of water has an osmolality of 2 Osm / kg (2000 mOsm / kg). Where solutions are defined herein to be “isotonic” with one another, the solutions have the same osmolality. For example, where a formulation is defined to be isotonic with human blood 25 serum, the formulation has the same osmolality as human blood serum. Human blood serum typically has an osmolality of about 275 to about 300 mOsm / kg (L. Hooper et al., BMJ Open, 2015; 5(10):e008846). “Syringeable” or “syringeability” refers to the force required to inject a given solution at a given rate via a chosen needle length and gauge, and relates to whether the formulation is30 administrable through a syringe. Flow through a hollow needle is characterized by the Hagen- Poiseuille equation (1): 44

[0041] ^^ =128QμLAπ^^4(1) where F = syringe stopper (plunger) force, Q = volumetric flow rate, µ = dynamic viscosity, L = needle length, D = needle bore diameter, and A = syringe area. Unless stated otherwise, concentrations expressed in terms of weight per volume (w / v) are 5 calculated from grams (g) per milliliter (mL). These concentrations may be expressed as a percentage (% w / v), for example, the concentration of 1 g of solute in 100 mL of a solution is 1% w / v. As used herein, and unless otherwise specified, a “neuropsychiatric disease or disorder” is a behavioral or psychological problem associated with a known neurological condition, and 10 typically defined as a cluster of symptoms that co-exist. Examples of neuropsychiatric disorders include, but are not limited to, schizophrenia, cognitive deficits in schizophrenia, attention deficit disorder, attention deficit hyperactivity disorder, cognitive deficit disorders, seizures, palsies, headache disorders, addictions, eating disorders, anger, bipolar and manic disorders, depression disorders, anxiety disorders, or any combinations thereof. 15 “Inflammatory conditions” or “inflammatory disease,” as used herein, refers broadly to chronic or acute inflammatory diseases. Inflammatory conditions and inflammatory diseases include, but are not limited to, rheumatic diseases (e.g., rheumatoid arthritis, osteoarthritis, psoriatic arthritis); spondyloarthropathies (e.g., ankylosing spondylitis, reactive arthritis, Reiter's syndrome); crystal arthropathies (e.g., gout, pseudogout, calcium pyrophosphate 20 deposition disease); multiple sclerosis; Lyme disease; polymyalgia rheumatica; connective tissue diseases (e.g., systemic lupus erythematosus, systemic sclerosis, polymyositis, dermatomyositis, Sjogren's syndrome); vasculitides (e.g., polyarteritis nodosa, Wegener's granulomatosis, Churg- Strauss syndrome); inflammatory conditions including consequences of trauma or ischaemia, sarcoidosis; vascular diseases including atherosclerotic vascular disease, atherosclerosis, and 25 vascular occlusive disease (e.g., atherosclerosis, ischaemic heart disease, myocardial infarction, stroke, peripheral vascular disease), and vascular stent restenosis; ocular diseases including uveitis, corneal disease, iritis, iridocyclitis, glaucoma, cataracts, or any combinations thereof. All diseases and disorders listed herein may be defined as described in the Diagnostic and Statistical Manual of Mental Disorders (DSM-5), published by the American Psychiatric 30 Association, or in International Classification of Diseases (ICD), published by the World Health Organization. 45

[0042] As used herein “adjunctive therapy,” “adjuvant therapy,” and the like, refers to a therapy that is given in addition to a primary or initial therapy to improve or maximize effectiveness. For example, a subject diagnosed with a depressive disorder that is taking one or more antidepressant medications (e.g., an SSRI) as a primary or initial therapy, but has an inadequate response to or 5 has otherwise failed to achieve a desirable outcome with the antidepressant medication may be administered, as “adjunctive therapy,” a pharmaceutical formulation of the present disclosure, to improve or maximize treatment effectiveness. In this example with a depressive disorder, the adjunctive therapy may improve or maximize treatment effectiveness by reducing depressive symptom(s) compared to the primary or initial therapy alone. The primary or initial therapy and 10 the adjunctive therapy involving the pharmaceutical formulation of the present disclosure, can be, but need not be, prescribed and / or administered by the same person (e.g., clinician). For example, the primary or initial therapy (e.g., SSRI therapy) may be prescribed by a first clinician and self- administered by the patient, while the adjunctive therapy involving a pharmaceutical formulation of the present disclosure, may be prescribed and / or administered by a second clinician. 15 Alternatively, the primary or initial therapy (e.g., SSRI therapy) may be prescribed by a first clinician and self-administered by the patient, while the adjunctive therapy involving a pharmaceutical formulation of the present disclosure, may be prescribed and / or administered by the same (first) clinician. The term “inadequate response” as used herein refers to a lack of clinically meaningful 20 improvement in symptoms, for example as measured by one or more of the rating scales described herein. The inadequate response to an adequate course of treatment with an antidepressant medication(s) may be determined retrospectively or prospectively. Prospective determination of inadequate response refers to a determination made by the prescribing clinician or therapist following administration of part of a course of treatment. Retrospective determination refers to a 25 determination made by the prescribing clinician or therapist following administration of a full adequate course of treatment. As used herein, “peak effects,” “peak psychedelic effects,” “peak experiences,” and the like, refer to subjective effects on perception and consciousness which are intense—peak effects normally correlate with a score of ≥ 70 mm on the VAS any drug effect rating scale. In the case 30 of short-acting tryptamine psychedelics such as DMT, 5-MeO-DMT, and their analogs (e.g., deuterated analogs), peak effects in humans are associated with a drug plasma concentration of ≥ 40 ng / mL. 46

[0043] The phrase “effect size” refers to a statistical calculation that can be used to compare the efficacy of different agents by quantifying the size of the difference between treatments (“between- group”). It is a dimensionless measure of the difference in outcomes under two different treatment interventions. Effect sizes thus inform clinicians about the magnitude of treatment effects. Unless 5 stated otherwise, as used herein, the effect size is calculated from the difference between the mean within-group efficacy endpoint change resulting from a treatment group (e.g., administration of a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) and the mean within- group efficacy endpoint change resulting from placebo, using Cohen’s d method with the following formula:10 ^^ ^^ℎ ^^ ^^′ ^^ ^^ =^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ℎ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ − ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ℎ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^ ^^Cohen’s d is also known as the standardized mean difference. An effect size (Cohen’s d score) of zero means that the treatment and placebo have no differences in effect. An effect size (Cohen’s d score) greater than zero indicates the degree to which treatment is more efficacious 15 than placebo. Conventionally, it is considered that an effect size (Cohen’s d score) of 0.2 is small, 0.5 is medium, and 0.8 or higher is large. As used herein, the term “and / or” includes any and all combinations of one or more of the associated listed items. As used in the description herein and throughout the claims that follow, the meaning of “a”, “an”, and “the” includes plural reference as well as the singular reference 20 unless the context clearly dictates otherwise. The term “about” in association with a numerical value means that the value may vary up or down by 5%. For example, for a value of about 100, means 95 to 105 (or any value between 95 and 105). Pharmaceutical Formulation 25 Disclosed herein is an injectable pharmaceutical formulation comprising a psychopharmaceutical agent or drug, a release modifier such as a hyaluronate salt or a carboxymethyl cellulose salt, and an aqueous vehicle. The pharmaceutical formulation is suitable for injection, thus its administration in therapy typically comprises parenteral injection of the formulation through the skin or other external 30 boundary tissue, rather than through the alimentary canal, so that the active pharmaceutical ingredient(s) contained therein is administered, using gravity or force, directly into a blood vessel, 47

[0044] organ, tissue, or lesion. To be suitable for injection, i.e., “injectable” or “injectability,” it is meant that the formulation is in accordance with Pharmacopeial requirements of injections, for example as set forth in The United States Pharmacopeial (USP) Convention, General Requirements / <1> Injections, 33. For example, the injectable pharmaceutical formulations are prepared by methods 5 designed to ensure that they meet Pharmacopeial requirements for sterility, pyrogens, particulate matter, and other contaminants, and where appropriate, contain inhibitors of the growth of organisms (e.g., antimicrobial preservatives) and / or anti-oxidants. Examples of Pharmacopeial requirements include, but are not limited to, USP Pyrogen Test <151>, USP Bacterial Endotoxins Test <85>, USP Antimicrobial Effectiveness Testing <51>, USP Antimicrobial Agents—Content 10 <341>, USP Sterilization and Sterility Assurance of Compendial Articles <1211>, USP Particulate Matter in Injections <788>, and USP Sterility Tests <71>. For instance, to be suitable for injection, inter alia, the endotoxin limit defined on the basis of dose is equal to K / M, where K is the threshold human pyrogenic dose of endotoxin per kg of body weight, and M is equal to the maximum recommended human dose of product per kg of body weight in a single hour period; Escherichia 15 coli should be absent in 1 g of formulation; the total aerobic microbial count (TAMC) should be under 1,000 colony forming units (CFU) / g; and the total yeast and mold count (TYMC) should not exceed 100 CFU / g. To be suitable for injection, i.e., “injectable” or “injectability,” it is further meant that the pharmaceutical formulation is characterized as having physiochemical properties, such as pH, 20 osmolality, and viscosity, which enables administration through the skin or other external boundary tissue via needle, syringe, canula, catheter, or other suitable injection device without causing excessive tissue necrosis, pain, or inflammation (e.g., phlebitis) at the injection site. Injectable drug products generally have a pH of about 2 to 11 for IV and intramuscular injection, and a pH of about 3 to 9 for subcutaneous injection (Usach I, et al. Subcutaneous Injection of 25 Drugs: Literature Review of Factors Influencing Pain Sensation at the Injection Site. Adv Ther. 2019 Nov;36(11):2986-2996). pH values which are too high are associated with tissue necrosis, whereas pH values which are too low are associated with pain and inflammation at the injection site. Injectable drug products generally have an osmolality of 150 to 600 mOsm / kg, with osmolalities closest to that of human blood serum (275 to about 300 mOsm / kg) being preferred. 30 Hypertonic injection solutions with an osmolality above 600 mOsm / kg have been reported to possibly cause crenation of red blood cells and significant pain, while hypotonic solutions with an osmolality below 150 mOsm / kg may cause hemolysis and pain at the injection site (Roethlisberger 48

[0045] D. et al. If Euhydric and Isotonic Do Not Work, What Are Acceptable pH and Osmolality for Parenteral Drug Dosage Forms?, Journal of Pharmaceutical Sciences, 106(2), 2017, 446-456). Injectable drug products administered with common syringes and needle gauge generally have a viscosity of less than about 50 centipoise (cP), with higher viscosities sometimes requiring 5 injection forces too high for common syringes and gauge needles to withstand. The drug may not even be administrable through a syringe (may not be “syringeable”). However, some injectable drug products with much higher viscosities (>100 to 10,000+ cP) can be administered by injection, for example, when administering non-Newtonian fluids or when using injection devices designed for high viscosity fluids such as auto-injectors for high viscosity fluids. The pH, osmolality, and 10 viscosity of the pharmaceutical formulation of the present disclosure fall within the ranges reported to be suitable for injection, and suitable for subcutaneous injection in particular. The pharmaceutical formulation is typically in the form of a solution, although other dosage forms are also contemplated such as suspensions, emulsions, micelles, liposomes, microspheres, and nanosystems which are suitable for injection. Solid forms which are suitable for 15 solutions or suspensions in liquid prior to injection are also disclosed. In some embodiments, the pharmaceutical formulations are disclosed as ready-to-use sterile solutions. In some embodiments, the pharmaceutical formulations are disclosed as reconstituted solutions prepared from sterile dry soluble products, including lyophilized powders and hypodermic tablets, reconstituted with an aqueous vehicle prior to use. In some embodiments, the pharmaceutical formulations are disclosed 20 as ready-to-use sterile suspensions. In some embodiments, the pharmaceutical formulations are disclosed as reconstituted solutions prepared from sterile dry insoluble products reconstituted with an aqueous vehicle prior to use. In some embodiments, the pharmaceutical formulations are disclosed as ready-to-use sterile emulsions. In some embodiments, the injectable pharmaceutical formulation is suitable for 25 intravenous administration (directly into the vein), i.e., is an intravenous pharmaceutical formulation. In some embodiments, the injectable pharmaceutical formulation is suitable for intramuscular administration (within the muscle), i.e., is an intramuscular pharmaceutical formulation. In some embodiment, the injectable pharmaceutical formulation is suitable for intradermal administration intradermally (beneath the skin), i.e., is an intradermal pharmaceutical 30 formulation. In some embodiments, the injectable pharmaceutical formulation is suitable for subcutaneous administration (within the fat or the layer of skin directly below the dermis and epidermis), i.e., is a subcutaneous pharmaceutical formulation. 49

[0046] Subcutaneous administration is a minimally invasive mode of administration. Subcutaneous tissue has few blood vessels and so drugs injected into it are intended for slow, sustained rates of absorption, often with some amount of depot effect. Compared with other routes of administration, it is slower than intravenous and intramuscular injections but still faster than 5 intradermal injections. The convenience and speed of subcutaneous delivery allows increased patient compliance and quicker access to medication when needed. Subcutaneous administration can be performed by injection or by implantation of a sustained or timed-release device beneath the surface of the skin. The site of the injection or device can be rotated when multiple injections or devices are needed. Subcutaneous formulations are usually much easier to handle for both the 10 patient and practitioner. A particular advantage of the subcutaneous delivery route in the therapeutic methods of the present disclosure is that it allows the medical practitioner to perform the administration in a rather short intervention with the patient, compared to intravenous infusion protocols associated with DMT-based therapy. Moreover, the patient can be trained to perform self-administration. Such self-administration may be particularly useful during maintenance 15 dosing where clinical observation and / or psychotherapy may play less prominent roles in the overall treatment. Usually, injection volumes of up to about 3 mL are tolerated via the subcutaneous route, especially those given in the patient’s abdomen, with injection volumes of about 2 mL or less being well tolerated across various injection sites. Large subcutaneous injection volumes greater than about 3 mL are often associated with pain. For patients requiring 20 multiple doses, several unit dose formulations can be injected at multiple sites of the body surface. Particular pharmacopeial requirements for subcutaneous injections include, but are not limited to, passing specifications of USP Particulate Matter in Injections <788>. The pharmaceutical formulation may be suitable for bolus injection, in which a discrete amount of the psychopharmaceutical agent is administered by injection within 30 minutes or less, 25 25 minutes or less, 20 minutes or less, 15 minutes or less, 10 minutes or less, 5 minutes or less, 4 minutes or less, 3 minutes or less, 2 minutes or less, 1 minute or less, 30 seconds or less, 20 seconds or less, 10 seconds or less, or 5 seconds or less. The bolus injection may involve a single injection or multiple injections performed within the above-described time range. Thus, administering multiple bolus injections within the above-mentioned time range of 30 minutes or less (e.g., two 30 injections lasting 30 seconds each, administered within 5 minutes of one another) would be considered a bolus administration herein. In some embodiments, the bolus injection involves a single injection within the above time range. The pharmaceutical formulation may be suitable for 50

[0047] bolus subcutaneous injection, such as a single bolus subcutaneous injection, i.e., the pharmaceutical formulation is a bolus subcutaneous pharmaceutical formulation. The pharmaceutical formulation may be suitable for bolus intramuscular injection, such as a single bolus intramuscular injection, i.e., the pharmaceutical formulation is a bolus intramuscular 5 pharmaceutical formulation. The pharmaceutical formulation may be suitable for bolus intradermal injection, such as a single bolus intradermal injection, i.e., the pharmaceutical formulation is a bolus intradermal pharmaceutical formulation. The pharmaceutical formulation may be suitable for bolus intravenous injection, such as a single bolus intravenous injection, i.e., the pharmaceutical formulation is a bolus intravenous pharmaceutical formulation. 10 The pharmaceutical formulation may be suitable for infusion injection, in which a discrete amount of the psychopharmaceutical agent is administered by injection over a prolonged period of greater than 30 minutes, greater than 40 minutes, greater than 50 minutes, greater than 60 minutes, greater than 70 minutes, greater than 80 minutes, greater than 90 minutes, greater than 100 minutes, greater than 110 minutes, greater than 120 minutes. The infusion injection may15 involve a single prolonged injection, or multiple injections (short or prolonged) within the above- described time range. Thus, administering multiple bolus injections over a prolonged period of greater than 30 minutes would be considered an infusion administration herein. In some embodiments, the infusion injection involves a single injection within the above time range. The pharmaceutical formulation may be suitable for infusion subcutaneous injection. The 20 pharmaceutical formulation may be suitable for infusion intramuscular injection. The pharmaceutical formulation may be suitable for infusion intravenous injection. Psychopharmaceutical agent The injectable pharmaceutical formulation comprises a psychopharmaceutical agent. The 25 psychopharmaceutical agent may be an anxiolytic (e.g., benzodiazepines, barbiturates, etc.), an empathogen-entactogen (e.g., MDMA, MDA, AMT, etc.), a stimulant (e.g., amphetamines, modafinil, etc.), a depressant (e.g., sedatives, hypnotics, and opioids), and / or a hallucinogen such as a psychedelic (e.g., a tryptamine psychedelic), a dissociative, or a deliriant (e.g., psilocybin, LSD, DMT, mescaline, salvia divinorum, scopolamine, etc.). The psychopharmaceutical agent 30 may be a free base compound, or a pharmaceutically acceptable salt of the free base compound. Combinations of psychopharmaceutical agents may also be used. 51

[0048] In some embodiments, the psychopharmaceutical agent is a dissociative, a dissociative hallucinogen, an anesthetic, an arylcyclo-hexylamine, a 1,2-diarylethylamine, a β-keto- arylcyclohexylamine, and / or a compound that modulates the NMDA receptor. Examples of such psychopharmaceutical agents include, but are not limited to, ketamine, methoxetamine, 5 deschloroketamine, N-ethyl deschloroketamine (eticyclidone), 3-methoxyphencyclidine, methoxieticyclidine, ephenidine, lanicemine, dextromethorphan, dextrorphan, methoxyketamine, norketamine (e.g., (R)-norketamine, (S)-norketamine, or mixtures thereof), hydroxynorketamine (e.g., 2R,6R-hydroxynorketamine, 2S,6S-hydroxynorketamine, or mixtures thereof), or a pharmaceutically acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination 10 thereof. In some embodiments, the psychopharmaceutical agent is an opioid. Examples of opioids include, but are not limited to, racemorphan, levorphanol, racemethorphan, buprenorphine, morphine, loperamide, morphine, codeine, hydrocodone, oxymorphone, buprenorphine, fentanyl, methadone, tramadol, alpha-methyl acetyl fentanyl, alfentanil, butyrfentanyl, carfentanil, 3-15 methylcarfentanil, 4-fluorofentanyl, beta-hydroxyfentanyl, alpha-methylfentanyl, cis-3- methylfentanyl, beta-hydroxy-3-methylfentanyl, remifentanil, sufentanil, 3-methylthiofentanyl, naloxone, and naltrexone, or a pharmaceutically acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination thereof. In some embodiments, the psychopharmaceutical agent is a cathinone, a 3,4- 20 methylenedioxyamphetamine compound, an aminoalkyl-substituted benzofuran, a substituted amphetamine, an aminoindane, a stimulant, diphenhydramine, hydroxazine, phenylephrine, dopamine, adrenaline, lidocaine, oxymetazoline, clemastine, chlorpheniramine, or 6-chloro-2- aminotetralin. In some embodiments, the pharmaceutical compound is a cathinone, an aminoalkyl- substituted benzofuran, and an aminoindane, or a pharmaceutically acceptable salt, a stereoisomer, 25 solvate, or prodrug thereof. In some embodiments, the psychopharmaceutical agent is a lysergamide. Examples of lysergamides include, but are not limited to, methylisopropyllysergamide, ethylisopropyllysergamide, 6-allyl-6-nor-LSD, 6-ethyl-6-nor-lysergic acid diethylamide, 1-acetyl- LSD, 1-propionyl-6-ethyl-6-nor-lysergic acid diethylamide, 1-propionyl-lysergic acid 30 diethylamide, 1-cyclopropionyl-d-lysergic acid diethylamide, N1-butyryl-lysergic acid diethylamide, and 6-propyl-6-nor-lysergic acid diethylamide, or a pharmaceutically acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination thereof. 52

[0049] In some embodiments, the psychopharmaceutical agent is a phenethylamine. Examples of phenethylamines include, but are not limited to, mescaline, 2,5-dimethoxy-4- bromophenethylamine (2C-B), 2-(4-iodo-2,5-dimethoxyphenyl)ethan-1-amine (2C-I), 2-(4- chloro-2,5-dimethoxyphenyl)ethan-1-amine (2C-C), 2,5-dimethoxy-4-iodoamphetamine, 2-[2,5- 5 dimethoxy-4-(propylsulfanyl)phenyl]ethan-1-amine, and 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2- methoxyphenyl)methyl]ethanamine, or a pharmaceutically acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination thereof. In some embodiments, the psychopharmaceutical agent is a tryptamine psychedelic. Examples of tryptamine psychedelics include, but are not limited to, N,N-dimethyltryptamine,10 N,N-diethyltryptamine, N,N-dipropyltryptamine, N-Methyl-N-propyltryptamine, N-methyl-N- isopropyltryptamine, N,N-diallyltryptamine, N-methyl-N-allyltryptamine, N-methyl-N- ethyltryptamine, N,N-diisopropyltryptamine, 4-hydroxy-N-methyl-N-ethyltryptamine, 5- methoxy-N,N-diisopropyltryptamine, 5-methoxy-N,N-dimethyltryptamine, O-acetylpsilocin, psilocin, as well as those tryptamine psychedelics described hereinafter, or a pharmaceutically 15 acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination thereof. Examples of psychopharmaceutical agents which can be categorized as hallucinogens such as a psychedelic (e.g., a tryptamine psychedelic), a dissociative, or a deliriant include, but are not limited to, 9,10-didehydro-6-allyl-N,N-diethylergoline-8β-carboxamide, 9,10-didehydro-6,N,N- triethylergoline-8β-carboxamide, N,N-dimethyltryptamine, N,N-diethyltryptamine, 5-methoxy-20 N,N-dimethyltryptamine, N,N-dibutyltryptamine, N,N-diethyltryptamine, N,N- diisopropyltryptamine, N,N-dipropyltryptamine, N-methyl-N-propyltryptamine, N-methyl-N- isopropyltryptamine, N,N-diallyltryptamine, N-methyl-N-allyltryptamine, N-methyl-N- ethyltryptamine, 4-hydroxy-N-methyl-N-ethyltryptamine, 5-methoxy-N,N- diisopropyltryptamine, 5-Methoxy-α-methyltryptamine, 2,α-dimethyltryptamine, α,N- 25 dimethyltryptamine, N,N-dipropyltryptamine, N-ethyl-N-isopropyltryptamine, α-ethyltryptamine, O-acetylpsilocin, psilocin, harmaline (7-methoxy-1-methyl-p-carboline), harmine (7-Methoxy-p- carboline), 4-hydroxy-diethyltryptamine and phosphate ester, 4-hydroxy-diisopropyltryptamine, 4-hydroxy-methyl-tryptamine, 4-hydroxy-tryptamine, 5-hydroxy-tryptamine, 4-hydroxy- dipropyltryptamine, 4-hydroxy-N-methyl-N-ethyl-tryptamine, 4-hydroxy-N-methyl-N-isopropyl-30 tryptamine, 4-hydroxy-N-N-tetramethylene-tryptamine, d-iso-LSD, I-LSD, I-iso-LSD, N,N- diisopropyl-4,5-methylenedioxy tryptamine, N,N-diisopropyl-5,6-methylenedioxy tryptamine, N,N-dimethyl-4,5-methylenedioxy tryptamine, N,N-dimethyl-5,6-methylenedioxy tryptamine, 2- 53

[0050] methyl-DMT, 5-MeO-diethyltryptamine, 5-MeO-diisopropyltryptamine, 4-MeO-N-isopropyl-N- methyl-tryptamine, 5-MeO-N-isopropyl-N-methyl-tryptamine, 5-MeO-NMT, 5-MeO-2,N,N- trimetyltryptamine, N-isopropyl-N-methyl-tryptamine, alpha-methyltryptamine, alpha-methyl-4- OH-tryptamine, N-methyl-tryptamine, 5-MeO-α,N-dimethyl-tryptamine, 4-allyloxy-3,5- 5 dimethoxyphenethylamine, 2,5-dimethoxy-4-methylthioamphetamine, 2,5-dimethoxy-4- ethylthioamphetamine, 2,5-dimethoxy-4-i-propylthioamphetamine, 2,5-dimethoxy-4- phenylthioamphetamine, 2,5-dimethoxy-4-n-propylthioamphetamine, 2,5-dimethoxy-α-ethyl-4- methylphenethylamine, 3,4-diethoxy-5-methoxy-phenethylamine, 4-n-butoxy-3,5-dimethoxy- phenethylamine, 2,5-dimethoxy-4,N-dimethylamphetamine, 4-bromo-2,5-β-10 trimethoxyphenethylamine, 4-methyl-2,5,β-trimethoxyphenethylamine, β-methoxy-3,4- methylenedioxyphenethylamine, 3,4,5,β-tetramethoxyphenethylamine, 3,5-dimethoxy-4- bromoamphetamine, 2-bromo-4,5-methylenedioxyamphetamine, 4-bromo- 2,5,dimethoxyphenethylamine, 4-benzyloxy-3,5-dimethoxyamphetamine, 2,5-dimethoxy-4- chlorophenethylamine, 2,5-dimethoxy-4-methylphenethylamine, 2,5-dimethoxy-4-15 ethylphenethylamine, 3,5-dimethoxy-4-ethoxyamphetamine, 2,5-dimethoxy-4- fluorophenethylamine, 2,5-dimethoxy-3,4-dimethylphenethylamine, 2,5-dimethoxy-3,4- (trimethylene)phenethylamine, 2,5-dimethoxy-3,4-(tetramethylene)phenethylamine, 3,6- dimethoxy-4-(2-aminoethyl)benzonorborane, 1,4-dimethoxynapthyl-2-ethylamine, 2,5- dimethoxyphenethylamine, 2,5-dimethoxy-4-iodoophenethylamine, 2,5-dimethoxy-4-20 nitrophenethylamine, 2,5-dimethoxy-4-i-propoxyphenethylamine, 2,5-dimethoxy-4-n- propoxyphenethylamine, 4-cyclopropyl-3,5-dimethoxyphenethylamine, 2,5-dimethoxy-4- methylseleneophenethylamine, 2,5-dimethoxy-4-methylthiophenethylamine, 2,5-dimethoxy-4- ethylthiophenethylamine, 2,5-dimethoxy-4-i-propylthiophenethylamine, 2,6-dimethoxy-4-i- propylthiophenethylamine, 2,5-dimethoxy-4-n-propylthiophenethylamine, 2,5-dimethoxy-4-25 cyclopropylmethylthiothiophenethylamine, 2,5-dimethoxy-4-t-butylthiophenethylamine, 2,5- dimethoxy-4-(2-methoxyrthylthio)phenethylamine, 2,5-dimethoxy-4- cyclopropylthiophenethylamine, 2,5-dimethoxy-4-s-butylthiophenethylamine, 2,5-dimethoxy-4- (2-fluorothio)phenethylamine, 2,5-dimethoxy-4-trideuteromethoxyphenethylamine, 2,4,5- trimethoxy-β,β-dideuterophenethylamine, 2,5-dimethoxy-4-methylphenethylamine, 2,4-30 dimethoxyamphetamine, 2,5-dimethoxyamphetamine, 2,4-dimethoxyamphetamine, 2,5- dimethoxy-3,4-methylenedioxyamphetamine, 2,5-dimethoxy-4-bromoamphetamine, 2,5- dimethoxy-4-chloroamphetamine, 2,5-dimethoxy-4-(2-fluoroethyl)-amphetamine, 2,5- 54

[0051] dimethoxy-4-iodoamphetamine, 2,5-dimethoxy-4-methylamphetamine, 2,6-dimethoxy-4- methylamphetamine, 2,5-dimethoxy-4-n-propylamphetamine, 3,5-dimethoxy-4- ethoxyphenethylamine, 2,4,5-triethoxyamphetamine, 2,4-diethoxy-5-methoxyamphetamine, 2,5- diethoxy-4-methoxyamphetamine, 4,5-dimethoxy-2-ethoxyamphetamine, N-hydroxy-N-methyl- 5 3,4-methylenedioxyamphetamine, 2,5-dimethoxy-3,4-(trimethylene)amphetamine, 3,6- dimethoxy-4-(2-aminopropyl)benzonorborane, 2,5-dimethoxy-3,4-dimethylamphetamine, 2,5- dimethoxy-4-ethylthio-N-hydroxyphenethylamine, 2,5-dimethoxy-N-hydroxy-4-n- propylthiophenethylamine, 2,5-dimethoxy-4-s-butylthio-N-hydroxyphenethylamine, 3,5- dimethoxy-4-i-propoxyphenethylamine, 5-ethoxy-2-methoxy-4-methylamphetamine, 2-amino-10 (3,4-methylenedioxyphenyl)butane, 3-methoxy-4,5-methylenedioxyphenethylamine, 3,4,5- trimethoxyphenethylamine, 3,5-dimethoxy-4-methalloxyphenethylamine, 3,4- methylenedioxyamphetamine, 3,4-methylenedioxy-N-ethylamphetamine, 3,4-methylenedioxy-N- methylamphetamine, 3,4-methylenedioxy-N-hydroxyamphtamine, 3,4-methylenedioxy-5- ethoxyphenethylamine, 2,5-dimethoxy-4-ethoxyapmphetamine, 3-methoxy-4-15 ethoxyphenethylamine, 2-methylamino-1-(3,4-methylenedioxyphenyl)butane, 3-methoxy-4,5- methylenedioxyamphetamine, 2-methoxy-4,5-methylenedioxyamphetamine, 2-methoxy-3,4- methylenedioxyamphetamine, 4-methoxy-2,3-methylenedioxyamphetamine, 3,5-dimethoxy-4-n- propoxyphenethylamine, 4-ethoxy-5-methoxy-3-methylthiophenethylamine, 3,5-dimethoxy-4- ethylthiophenethylamine, 3,4-dimethoxy-5-methylthiophenethylamine, 3,5-dimethoxy-5-20 methylthiophenethylamine, 3,4,5-trimethoxyamphetamine, 2,4,5-trimethoxyamphetamine, 2,3,5- trimethoxyamphetamine, 2,3,6-trimethoxyamphetamine, 2,4,6-trimethoxyamphetamine, 4,5- dimethoxy-3-ethylthiophenethylamine, 4-ethyl-2-methoxy-5-methylthioamphetamine, 5- methoxy-4-methyl-2-methylthioamphetamine, 2-methoxy-4-methyl-5-methylthioamphetamine, 2-methoxy-4-methyl-5-methylsulfinylamphetamine, 3,5-dimethoxy-4-n- 25 propylthiophenethylamine, salvinorin A, ibotenic acid, muscimol, dextromethorphan, ketamine, esketamine (the S(+)-enantiomer of ketamine), norketamine (e.g., (R)-norketamine, (S)- norketamine, or mixtures thereof), hydroxynorketamine (e.g., 2R,6R-hydroxynorketamine, 2S,6S- hydroxynorketamine, or mixtures thereof), phencyclidine, dizocilpine (MK-801), scopolamine, hyoscyamine, aporphine, lysergic acid amide, cathine, cathinone, and voacangine, or a 30 pharmaceutically acceptable salt, a stereoisomer, solvate, or prodrug thereof, or a combination thereof. Tryptamine psychedelic 55

[0052] In some embodiments, the psychopharmaceutical agent is a tryptamine psychedelic. Tryptamine psychedelics generally share a basic core structure of an indole (a fused a fused benzene and pyrrole ring), and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen), as represented below. Many tryptamine 5 psychedelics are 5-HT2A receptor agonists, i.e., they increase the activity of a 5-HT2A receptor, which is a subtype of the 5-HT2receptor that belongs to the serotonin receptor family, and includes both partial and full agonists. In some embodiments, the tryptamine psychedelic is optionally substituted on the 10 tryptamine ring. In some embodiments, the tryptamine psychedelic is an N,N-dialkyltryptamine. In some embodiments, the tryptamine psychedelic is N,N-dimethyltryptamine, N,N- diethyltryptamine, N,N-dipropyltryptamine, N-methyl-N-propyltryptamine, N-methyl-N- isopropyltryptamine, N,N-diallyltryptamine, N-methyl-N-allyltryptamine, N-methyl-N- ethyltryptamine, N,N-diisopropyltryptamine, wherein the tryptamine is optionally substituted, or 15 a combination thereof. In some embodiments, the tryptamine psychedelic is substituted with one or more deuterium atoms. In some embodiments, the tryptamine psychedelic is optionally substituted at the 4- or 5-position of the tryptamine ring with a substituent selected from hydroxy, acetoxy, or methoxy. In some embodiments, the tryptamine is 4-hydroxy-N-methyl-N- ethyltryptamine, psilocin, 5-methoxy-N,N-diisopropyltryptamine, 5-methoxy-N,N- 20 dimethyltryptamine, or O-acetylpsilocin (4-acetoxy-N,N-dimethyltryptamine), or a combination thereof. The tryptamine psychedelic may be a pharmaceutically acceptable salt of a compound of the present disclosure, e.g., a compound of Formula (I) through (III), defined hereinafter. The tryptamine psychedelic may be a pharmaceutically acceptable salt of a single compound of the 25 present disclosure or a pharmaceutically acceptable salt of a mixture of compounds of the present 56

[0053] disclosure. The injectable pharmaceutical formulation comprises (as the tryptamine psychedelic) a pharmaceutically acceptable salt of a compound of the present disclosure, e.g., a compound of Formula (I) through (III), when it comprise ions (protonated forms) of the compounds of the present disclosure and ions that counter the charge of the compounds of the present disclosure 5 (counterions) in solution. Accordingly, the pharmaceutically acceptable salt of a compound of the present disclosure (e.g., e.g., a compound of Formula (I) through (III)) may be pre-formed, for example as a fumarate salt of a compound of the present disclosure, and subsequently combined with the release modifier and the aqueous vehicle, to form the injectable pharmaceutical formulation. In other words, the injectable pharmaceutical formulation may be prepared from a 10 pre-formed, typically solid form and in some cases crystalline solid form, of the pharmaceutically acceptable salt of a compound of the present disclosure (e.g., a compound of Formula (I) through (III)). Alternatively, the pharmaceutically acceptable salt of a compound of the present disclosure within the pharmaceutical formulation may be formed in-situ, for example, by contacting the compound of the present disclosure (e.g., a compound of Formula (I) through (III)) as a free base 15 with an aqueous vehicle comprising available H+(aq) ions capable of ionizing / protonating the compounds of the present disclosure. While a distribution of free base and protonated species (salt form) of the compound may exist in solution depending on the pH of the pharmaceutical formulation, the pharmaceutical formulation generally contains a molar proportion of protonated compound (salt form) of least 10%, at least 20%, at least 30%, at least 40%, at least 50%, at least 20 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 99%. In most cases, the pharmaceutical formulation contains a molar proportion of protonated compound (salt form) of least 80%, at least 90%, at least 95%, at least 99%, at least 99.5%, at least 99.9% for most favorable aqueous solubility. In some embodiments, the tryptamine psychedelic is a pharmaceutically acceptable salt of 25 a compound of Formula (I), or a stereoisomer, solvate, or prodrug thereof, 57

[0054] wherein: X1and X2are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted 5 alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; Y1 and Y2 are independently selected from the group consisting of hydrogen and deuterium; R2is selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or 10 substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; R4and R5are independently selected from the group consisting of hydrogen, deuterium, hydroxyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy, unsubstituted or 15 substituted alkylthio, and unsubstituted or substituted acyloxy; R6and R7are independently selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; and 20 R8 and R9 are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, or alternatively R8 and R9 together with the nitrogen atom attached thereto are optionally 58

[0055] joined to form an unsubstituted or substituted heterocycloalkyl. X1and X2may be the same, or different. In some embodiments, X1and X2are the same. In some embodiments, X1and X2are hydrogen. In some embodiments, X1and X2are deuterium. In some embodiments, X1 and X2 are different. In some embodiments, X1 is hydrogen or 5 deuterium, and X2 is a substituted or unsubstituted C1-C6 alkyl. In some embodiments, X2 is an unsubstituted C1-C6alkyl, examples of which include, but are not limited to, methyl, ethyl, and n- propyl, preferably methyl. In some embodiments, X2 is a substituted C1-C6 alkyl. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1 alkyl group (i.e., methyl group), the substituted C1alkyl group may 10 be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In some embodiments, one of X1 and X2 is deuterium while the other is hydrogen. In some embodiments, one or more of X1 and X2 is a substituted or unsubstituted C3-C10cycloalkyl. In some embodiments, one or more of X1and X2is an unsubstituted C3-C10cycloalkyl, examples of which may include, but are not limited to, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. In some 15 embodiments, one or more of X1 and X2 is a substituted C3-C10 cycloalkyl. Preferred substituents may include, but are not limited to, alkyl, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The cycloalkyl group may contain one, or more than one, substituent. In some embodiments, X1 and / or X2 is an unsubstituted or substituted alkenyl, e.g., an unsubstituted or substituted allyl. 20 Y1and Y2may be the same, or different. In some embodiments, Y1and Y2are the same. In some embodiments, Y1 and Y2 are hydrogen. In some embodiments, Y1 and Y2 are deuterium. In some embodiments, Y1and Y2are different. In some embodiments, one of Y1and Y2is deuterium while the other is hydrogen. In some embodiments, R2 is deuterium. In some embodiments, R2 is hydrogen. In some 25 embodiments, R2 is a halogen, e.g., fluoro, chloro, bromo, and iodo. In some embodiments, R2 is an unsubstituted C1-C6alkyl, examples of which include, but are not limited to, methyl, ethyl, n- propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, neopentyl, and hexyl. In some embodiments, R2 is a substituted C1-C6 alkyl. When R2 is a substituted C1-C6 alkyl, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar 30 substituents such as hydroxyl or polyether substituents, etc. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1 alkyl group (i.e., methyl group), the substituted C1 alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In 59

[0056] some embodiments, R2 is an unsubstituted or substituted alkenyl, e.g., an unsubstituted or substituted allyl. In some embodiments, R2is an unsubstituted or substituted alkynyl. In some embodiments, R2is a substituted or unsubstituted C3-C10cycloalkyl. In some embodiments, R2is an unsubstituted C3-C10 cycloalkyl, examples of which may include, but are not limited to, 5 adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. In some embodiments, R2is a substituted C3-C10cycloalkyl. Preferred substituents may include, but are not limited to, alkyl, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The cycloalkyl group may contain one, or more than one, substituent. In some embodiments, R2is an unsubstituted or substituted heterocycloalkyl. In some 10 embodiments, R2 is an unsubstituted or substituted aryl. In some embodiments, R2 is an unsubstituted or substituted heteroaryl. R4and R5may be the same, or different. In some embodiments, R4is deuterium. In some embodiments, R4is hydrogen. In some embodiments, R4is hydroxyl. In some embodiments, R4is an unsubstituted C1-C6 alkyl, examples of which include, but are not limited to, methyl, ethyl, n- 15 propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, neopentyl, and hexyl. In some embodiments, R4is a substituted C1-C6alkyl. When R4is a substituted C1-C6alkyl, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1alkyl group (i.e., methyl 20 group), the substituted C1alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In some embodiments, R4 is an unsubstituted alkoxy group, examples of which include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, n-pentoxy, neopentoxy, and hexoxy. In some embodiments, R4is a substituted alkoxy. When R4is a substituted alkoxy, preferred substituents may include, but are not limited to, deuterium, halogen 25 (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkoxy group may contain one, or more than one, substituent. For example, when the alkoxy group is a C1alkoxy group (i.e., methoxy group), the substituted C1 alkoxy group may be -OCDH2, -OCD2H, -OCD3, -OCFH2, -OCF2H, -OCF3, etc. In some embodiments, R4 is an unsubstituted alkylthio, examples of which include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n- 30 butylthio, isobutylthio, sec-butylthio, t-butylthio, n-pentylthio, neopentylthio, and hexylthio. In some embodiments, R4 is a substituted alkylthio. The alkylthio group may contain one, or more than one, substituent. In some embodiments, R4is an alkylthio group substituted with one or more60

[0057] deuterium. The alkylthio group may contain one, or more than one, deuterium substituent. For example, when the alkylthio group is a C1alkylthio group (i.e., a methylthio group), the deuterium substituted C1alktlthio group may be -SCDH2, -SCD2H, and -SCD3. In some embodiments, R4is a haloalkylthio (an alkylthio substituted with one or more halogen atoms), examples of which 5 include, but are not limited to, -SCH2F, -SCHF2, -SCF3, -SCH2CH2F, -SCH2CHF2, -SCH2CF3, -SCH2CH2CH2F, -SCH2CH2CHF2, -SCH2CH2CF3, -SCH2CH2CH2CH2F, -SCH2CH2CH2CHF2, and -SCH2CH2CH2CF3, with particular mention being made to -SCH2F, -SCHF2, -SCF3. In some embodiments, R4 is an unsubstituted or substituted acyloxy, examples of which include, but are not limited to, acetoxy (-OCOCH3), propionoxy (-OCOCH2CH3), and butyroxy (- 10 OCOCH2CH2CH3). In some embodiments, R5 is deuterium. In some embodiments, R5 is hydrogen. In some embodiments, R5is hydroxyl. In some embodiments, R5is an unsubstituted C1-C6alkyl, examples of which include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec- butyl, t-butyl, n-pentyl, neopentyl, and hexyl. In some embodiments, R5 is a substituted C1-C6 15 alkyl. When R5 is a substituted C1-C6 alkyl, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1 alkyl group (i.e., methyl group), the substituted C1 alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In some embodiments, R5is an unsubstituted 20 alkoxy group, examples of which include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, t-butoxy, n-pentoxy, neopentoxy, and hexoxy. In some embodiments, R5is a substituted alkoxy. When R5is a substituted alkoxy, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkoxy group may contain one, or 25 more than one, substituent. For example, when the alkoxy group is a C1 alkoxy group (i.e., methoxy group), the substituted C1alkoxy group may be -OCDH2, -OCD2H, -OCD3, -OCFH2, - OCF2H, -OCF3, etc. In some embodiments, R5 is an unsubstituted alkylthio, examples of which include, but are not limited to, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, t-butylthio, n-pentylthio, neopentylthio, and hexylthio. In some 30 embodiments, R5is a substituted alkylthio. The alkylthio group may contain one, or more than one, substituent. In some embodiments, R5 is an alkylthio group substituted with one or more deuterium. The alkylthio group may contain one, or more than one, deuterium substituent. For 61

[0058] example, when the alkylthio group is a C1 alkylthio group (i.e., a methylthio group), the deuterium substituted C1alktlthio group may be -SCDH2, -SCD2H, and -SCD3. In some embodiments, R5is a haloalkylthio (an alkylthio substituted with one or more halogen atoms), examples of which include, but are not limited to, -SCH2F, -SCHF2, -SCF3, -SCH2CH2F, -SCH2CHF2, -SCH2CF3, 5 -SCH2CH2CH2F, -SCH2CH2CHF2, -SCH2CH2CF3, -SCH2CH2CH2CH2F, -SCH2CH2CH2CHF2, and -SCH2CH2CH2CF3, with particular mention being made to -SCH2F, -SCHF2, -SCF3. In some embodiments, R5 is an unsubstituted or substituted acyloxy, examples of which include, but are not limited to, acetoxy (-OCOCH3), propionoxy (-OCOCH2CH3), and butyroxy ( -OCOCH2CH2CH3). 10 R6 and R7 may be the same, or different. In some embodiments, R6 and R7 are the same. In some embodiments, R6 and R7 are different. In some embodiments, R6 is hydrogen. In some embodiments, R6is deuterium. In some embodiments, R6is a halogen, e.g., fluoro, chloro, bromo, and iodo. In some embodiments, R6is an unsubstituted or substituted alkyl (e.g., an unsubstituted or substituted a C1-C6 alkyl). In some embodiments, R6 is an unsubstituted C1-C6 alkyl, examples15 of which include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec- butyl, t-butyl, n-pentyl, neopentyl, and hexyl. In some embodiments, R6is a substituted C1-C6alkyl. When R6 is a substituted C1-C6 alkyl, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkyl group may contain one, or more than one, substituent. For example, 20 when the alkyl group is a C1alkyl group (i.e., methyl group), the substituted C1alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In some embodiments, R6 is an unsubstituted or substituted alkenyl, e.g., an unsubstituted or substituted allyl. In some embodiments, R6is an unsubstituted or substituted alkynyl. In some embodiments, R6is an unsubstituted or substituted C3-C10 cycloalkyl. In some embodiments, R6 is an unsubstituted C3-C10 cycloalkyl, examples of 25 which may include, but are not limited to, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. In some embodiments, R6is a substituted C3-C10cycloalkyl. Preferred substituents may include, but are not limited to, alkyl, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The cycloalkyl group may contain one, or more than one, substituent. In some embodiments, R6is an unsubstituted or substituted 30 heterocycloalkyl. In some embodiments, R6is an unsubstituted or substituted aryl. In some embodiments, R6 is an unsubstituted or substituted heteroaryl. In some embodiments, R7 is hydrogen. In some embodiments, R7 is deuterium. In some 62

[0059] embodiments, R7 is a halogen, e.g., fluoro, chloro, bromo, and iodo. In some embodiments, R7 is an unsubstituted or substituted alkyl (e.g., an unsubstituted or substituted a C1-C6alkyl). In some embodiments, R7is an unsubstituted C1-C6alkyl, examples of which include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, t-butyl, n-pentyl, neopentyl, and 5 hexyl. In some embodiments, R7 is a substituted C1-C6 alkyl. When R7 is a substituted C1-C6 alkyl, preferred substituents may include, but are not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1 alkyl group (i.e., methyl group), the substituted C1alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In 10 some embodiments, R7 is an unsubstituted or substituted alkenyl, e.g., an unsubstituted or substituted allyl. In some embodiments, R7 is an unsubstituted or substituted alkynyl. In some embodiments, R7is an unsubstituted or substituted C3-C10cycloalkyl. In some embodiments, R7is an unsubstituted C3-C10cycloalkyl, examples of which may include, but are not limited to, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. In some 15 embodiments, R7 is a substituted C3-C10 cycloalkyl. Preferred substituents may include, but are not limited to, alkyl, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The cycloalkyl group may contain one, or more than one, substituent. In some embodiments, R7 is an unsubstituted or substituted heterocycloalkyl. In some embodiments, R7is an unsubstituted or substituted aryl. In some embodiments, R7is an 20 unsubstituted or substituted heteroaryl. R8 and R9 may be the same, or different. In some embodiments, R8 and R9 are the same. In some embodiments, R8and R9are hydrogen. In some embodiments, R8and R9are deuterium. In some embodiments, R8and R9are unsubstituted or substituted alkyl, such as an unsubstituted or substituted C1-C6 alkyl. In some embodiments, R8 and R9 are different. In some embodiments, R8 25 is hydrogen, and R9 is an unsubstituted or substituted C1-C6 alkyl. In some embodiments, R8and / or R9is an unsubstituted C1-C6alkyl, examples of which include, but are not limited to, methyl, ethyl, n-propyl, and isopropyl, preferably methyl. In some embodiments, R8 and / or R9 is a substituted C1-C6 alkyl. The alkyl group may contain one, or more than one, substituent. For example, when the alkyl group is a C1alkyl group (i.e., methyl group), 30 the substituted C1alkyl group may be -CDH2, -CD2H, -CD3, -CFH2, -CF2H, -CF3, etc. In some embodiments, R8 and / or R9 is an alkyl substituted with one or more deuterium, e.g., a C1-C6 alkyl group substituted with one or more deuterium. The alkyl group may contain one, or more than one, 63

[0060] deuterium substituent. For example, when the alkyl group is a C1 alkyl group (i.e., methyl group), the deuterium substituted C1alkyl group may be -CDH2, -CD2H, and -CD3, with particular mention being made to -CD3. In some embodiments, R8and / or R9is a haloalkyl, examples of which include, but are not limited to, -CH2CH2F, -CH2CHF2, -CH2CF3, -CH2CH2CH2F, -CH2CH2CHF2, - 5 CH2CH2CF3, -CH2CH2CH2CH2F, -CH2CH2CH2CHF2, and -CH2CH2CH2CF3, with particular mention being made to -CH2CH2CH2F, -CH2CH2CHF2, and -CH2CH2CF3. In some embodiments, R8 and / or R9 is an unsubstituted or substituted alkenyl, e.g., an unsubstituted or substituted allyl. In some embodiments, R8 and / or R9 is an unsubstituted or substituted alkynyl. In some embodiments, R8and / or R9is a substituted or unsubstituted C3-C10cycloalkyl. In some 10 embodiments, R8 and / or R9 is an unsubstituted C3-C10 cycloalkyl, examples of which may include, but are not limited to, adamantyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclooctyl. In some embodiments, R8and / or R9is a substituted C3-C10cycloalkyl. Preferred substituents may include, but are not limited to, alkyl, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl or polyether substituents, etc. The cycloalkyl group may contain 15 one, or more than one, substituent. In some embodiments, R8 and / or R9 is an unsubstituted or substituted heterocycloalkyl. In some embodiments, R8and / or R9is an unsubstituted or substituted aryl. In some embodiments, R8 and / or R9 is an unsubstituted or substituted heteroaryl. In some embodiments, R8 and R9 together with the nitrogen atom attached thereto are joined to form an unsubstituted or substituted heterocycloalkyl. In some embodiments, R8and R920 together with the nitrogen atom attached thereto are joined to form an unsubstituted heterocycloalkyl. The unsubstituted heterocycloalkyl group may be, e.g., a 3-membered ring, a 4- membered ring, 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, etc., which may be optionally fused to other ring(s). The unsubstituted heterocycloalkyl group contains a minimum of one nitrogen ring atom (the nitrogen atom intervening R8 and R9), and may 25 optionally contain at least one additional hetero-ring atom, which may be one or more of nitrogen, sulfur, or oxygen, for a total of 1, 2, 3, or 4 hetero-ring atoms (at least one of which is a nitrogen ring atom). Examples of unsubstituted heterocycloalkyl groups formed from joining R8 and R9 together with the nitrogen atom attached thereto include, but are not limited to, , , , , , 64

[0061] , , , , , , , , , , , and . In some embodiments, R8and R9together with the nitrogen atom attached thereto are 5 joined to form a substituted heterocycloalkyl. The substituted heterocycloalkyl group may be, e.g., a 3-membered ring, a 4-membered ring, a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, etc., which may be optionally fused to other ring(s). The substituted heterocycloalkyl group contains a minimum of one nitrogen ring atom (the nitrogen atom intervening R8 and R9), and may optionally contain additional hetero-ring atoms (e.g., nitrogen, 10 sulfur, or oxygen) for a total of 1, 2, 3, or 4 hetero-ring atoms (at least one of which is a nitrogen ring atom). Examples of the substituted heterocycloalkyl group include, but are not limited to, aziridine, azetidine, pyrrolidine, isoindole, indole, dihydroindole, indazole, purine, carbazole, carboline, imidazolidine, imidazoline, piperidine, piperazine, indoline, 1,2,3,4- tetrahydroisoquinoline, thiazolidine, morpholine, or thiomorpholine, which is substituted with at 15 least one substituent. The substituent(s) may be any recited herein, including, but not limited to, deuterium, halogen (e.g., fluorine), polar substituents such as hydroxyl, oxo, unsubstituted alkoxy, substituted alkoxy (e.g., polyether groups), unsubstituted alkyl, substituted alkyl, unsubstituted alkenyl, substituted alkenyl, unsubstituted alkynyl, substituted alkynyl, unsubstituted cycloalkyl, substituted cycloalkyl, unsubstituted heterocycloalkyl, substituted heterocycloalkyl, unsubstituted 20 aryl, substituted aryl, unsubstituted heteroaryl, and substituted heteroaryl. The substituted heterocycloalkyl formed from joining R8and R9together with the nitrogen atom attached thereto contains a heterocycloalkyl group substituted with one, two, three, four, or more substituents. The substituent may be located on a carbon ring atom or on a hetero-ring atom. 65

[0062] Examples of substituted heterocycloalkyl groups formed from joining R8 and R9 together with the nitrogen atom attached thereto include, but are not limited to, , , , , , , , , , 5 , , , and . In some embodiments, the tryptamine psychedelic is a pharmaceutically acceptable salt of a compound of Formula (I), or a stereoisomer, solvate, or prodrug thereof, wherein any one or more of X1, X2, Y1, Y2, R2, R4, R5, R6, R7, R8, and R9 optionally comprises deuterium. In some embodiments, at least one of X1, X2, Y1, Y2, R2, R4, R5, R6, R7, R8, and R9 comprises deuterium. 10 In some embodiments, at least one of X1, X2, Y1, Y2, R5, R8, and R9comprises deuterium. In some embodiments, at least one of X1, X2, Y1, Y2, R8, and R9 comprises deuterium. In some embodiments, X1, X2, R8, and R9 comprise deuterium. In some embodiments, X1, X2, Y1, Y2, R8, and R9comprise deuterium. In some embodiments, X1, X2, and R5comprise deuterium. In some embodiments, X1, X2, Y1, Y2, R5, R8, and R9 comprise deuterium. 15 In some embodiments, the tryptamine psychedelic is a pharmaceutically acceptable salt of a compound of Formula (II), or a stereoisomer, solvate, or prodrug thereof 66

[0063] wherein: X1 and X2 are independently hydrogen or deuterium, Y1 and Y2 are independently hydrogen or deuterium, 5 each Z1is independently hydrogen or deuterium, each Z2is independently hydrogen or deuterium, and R2, R4, R5, R6, and R7 are independently hydrogen or deuterium. X1 and X2 may be the same, or different. In some embodiments, X1 and X2 are the same. In some embodiments, X1and X2are hydrogen. In some embodiments, X1and X2are deuterium. 10 In some embodiments, X1 and X2 are different. In some embodiments, X1 is deuterium and X2 is hydrogen. Y1and Y2may be the same, or different. In some embodiments, Y1and Y2are the same. In some embodiments, Y1 and Y2 are hydrogen. In some embodiments, Y1 and Y2 are deuterium. In some embodiments, Y1 and Y2 are different. In some embodiments, Y1 is deuterium and Y2 is 15 hydrogen. In some embodiments, X1, X2, Y1, and Y2 are hydrogen. In some embodiments, X1, X2, Y1, and Y2 are deuterium. In some embodiments, each Z1is hydrogen. In some embodiments, each Z1is deuterium. In some embodiments, one Z1is hydrogen, while the other two Z1’s are deuterium. In some 20 embodiments, one Z1 is deuterium, while the other two Z1’s are hydrogen. In some embodiments, each Z2 is hydrogen. In some embodiments, each Z2 is deuterium. In some embodiments, one Z2 is hydrogen, while the other two Z2’s are deuterium. In some embodiments, one Z2is deuterium, while the other two Z2’s are hydrogen. In some embodiments, each Z1 and Z2 is hydrogen. In some 67

[0064] embodiments, each Z1 and Z2 is deuterium. In some embodiments, R2is deuterium. In some embodiments, R2is hydrogen. In some embodiments, R4is deuterium. In some embodiments, R4is hydrogen. In some embodiments, R5is deuterium. In some embodiments, R5 is hydrogen. In some embodiments, R6 is deuterium. In 5 some embodiments, R6 is hydrogen. In some embodiments, R7 is deuterium. In some embodiments, R7is hydrogen. R2, R4, R5, R6, and R7may be the same, for example, R2, R4, R5, R6, and R7 may each be hydrogen, or alternatively, R2, R4, R5, R6, and R7 may each be deuterium. In some embodiments, at least one of R2, R4, R5, R6, and R7 is deuterium, or at least two of R2, R4, R5, R6, and R7are deuterium, or at least three of R2, R4, R5, R6, and R7are deuterium, or at least four 10 of R2, R4, R5, R6, and R7 are deuterium. In some embodiments, at least one of X1, X2, Y1, Y2, Z1, Z2, R2, R4, R5, R6, and R7 is deuterium. In some embodiments, X1, X2, Z1and Z2are deuterium. In some embodiments, X1, X2, Y1, and Y2are deuterium. In some embodiments, X1, X2, Y1, Y2, Z1, and Z2are deuterium. In some embodiments, the tryptamine psychedelic is a pharmaceutically acceptable salt of 15 a compound of Formula (III), or a stereoisomer, solvate, or prodrug thereof wherein: X1and X2are independently hydrogen or deuterium, Y1and Y2are independently hydrogen or deuterium, 20 each Z1 is independently hydrogen or deuterium, each Z2 is independently hydrogen or deuterium, each Z3is independently hydrogen or deuterium, and R2, R4, R6, and R7 are independently hydrogen or deuterium. 68

[0065] X1 and X2 may be the same, or different. In some embodiments, X1 and X2 are the same. In some embodiments, X1and X2are hydrogen. In some embodiments, X1and X2are deuterium. In some embodiments, X1and X2are different. In some embodiments, X1is deuterium and X2is hydrogen. 5 Y1 and Y2 may be the same, or different. In some embodiments, Y1 and Y2 are the same. In some embodiments, Y1and Y2are hydrogen. In some embodiments, Y1and Y2are deuterium. In some embodiments, Y1 and Y2 are different. In some embodiments, Y1 is deuterium and Y2 is hydrogen. In some embodiments, X1, X2,Y1, and Y2are hydrogen. In some embodiments, X1, X2,Y1, 10 and Y2 are deuterium. In some embodiments, each Z1 is hydrogen. In some embodiments, each Z1 is deuterium. In some embodiments, one Z1is hydrogen, while the other two Z1’s are deuterium. In some embodiments, one Z1is deuterium, while the other two Z1’s are hydrogen. In some embodiments, each Z2 is hydrogen. In some embodiments, each Z2 is deuterium. In some embodiments, one Z2 15 is hydrogen, while the other two Z2’s are deuterium. In some embodiments, one Z2 is deuterium, while the other two Z2’s are hydrogen. In some embodiments, each Z1and Z2is hydrogen. In some embodiments, each Z1 and Z2 is deuterium. In some embodiments, each Z3 is hydrogen. In some embodiments, each Z3 is deuterium. In some embodiments, one Z3is hydrogen, while the other two Z3’s are deuterium. In some 20 embodiments, one Z3is deuterium, while the other two Z3’s are hydrogen. In some embodiments, each Z1, Z2, and Z3 is hydrogen. In some embodiments, each Z1 and Z2 is hydrogen and each Z3 is deuterium. In some embodiments, each Z1, Z2, and Z3is deuterium. In some embodiments, each Z1and Z2is deuterium, and each Z3is hydrogen. In some embodiments, R2 is deuterium. In some embodiments, R2 is hydrogen. In some 25 embodiments, R4 is deuterium. In some embodiments, R4 is hydrogen. In some embodiments, R6 is deuterium. In some embodiments, R6is hydrogen. In some embodiments, R7is deuterium. In some embodiments, R7 is hydrogen. R2, R4, R6, and R7 may be the same, for example, R2, R4, R6, and R7 may each be hydrogen, or alternatively, R2, R4, R6, and R7 may each be deuterium. In some embodiments, at least one of R2, R4, R6, and R7is deuterium, or at least two of R2, R4, R6, and R730 are deuterium, or at least three of R2, R4, R6, and R7are deuterium. In some embodiments, at least one of X1, X2, Y1, Y2, Z1, Z2, Z3, R2, R4, R6, and R7 is deuterium. In some embodiments, X1, X2, Z1 and Z2 are deuterium and each Z3 is hydrogen. In 69

[0066] some embodiments, X1, X2, Y1, and Y2 are deuterium and each Z3 is hydrogen. In some embodiments, X1, X2, Y1, Y2, Z1, and Z2are deuterium and each Z3is hydrogen. In some embodiments, X1, X2, and Z3are deuterium. In some embodiments, X1, X2, Z1, Z2, and Z3are deuterium. In some embodiments, X1, X2, Y1, Y2, and Z3 are deuterium. In some embodiments, 5 X1, X2, Y1, Y2, Z1, Z2, and Z3 are deuterium. In some embodiments, the tryptamine psychedelic is a pharmaceutically acceptable salt of a compound of Formula (I) through (III), which include, but are not limited to, the following exemplary compounds (I-1), (I-2), 10 (I-3), (I-4), (I-5), (I-6), 70

[0067] or a stereoisomer, solvate, or prodrug thereof, or a combination thereof.

[0068] In some embodiments, the compound, e.g., a compound of Formula (I) or (II), is a deuterated analog of DMT, examples of which include, but are not limited to,

[0069] (I-6), (I-7), (I-8), (I-9), (I-10), (I-11), (I-12), or a combination thereof. 5 In some embodiment, the deuterated analog of DMT is one or more of 2-(1H-indol-3-yl)- N,N-dimethylethan-1-amine-1,1-d2(I-2); 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine- 1,1,2,2-d4 (I-8); 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10); 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11); 2-(1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1-d2(I-6); 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2(I-7); 103 and 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In some embodiments, the compound, e.g., a compound of Formula (I) or (III), is a deuterated analog of 5-MeO-DMT, examples of which include, but are not limited to, 5 104

[0070] 5 In some embodiment, the deuterated analog of 5-MeO-DMT is one or more of 2-(5- methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-20); 2-(5-methoxy-1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-22); 2-(5-methoxy-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-23); 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1-d2(I-18); 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine- 106

[0071] 2,2-d2 (I-19); 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-24); 2-(5- (methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-34); 2-(5-(methoxy- d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-36); 2-(5-(methoxy-d3)-1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-37); 2-(5-(methoxy-d3)-1H-indol-3-yl)- 5 N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-32); 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-2,2-d2(I-33); 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,2-d2 (I-38); 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine- 1,1-d2 (I-28); 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-2,2-d2 (I-29); 2-(5- (methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1-d (I-26); 2-(5-(methoxy-d3)-1H-10 indol-3-yl)-N,N-dimethylethan-1-amine-2-d (I-27); and 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- dimethylethan-1-amine (I-25). Any position in the compounds defined herein as having deuterium have a minimum deuterium incorporation that is greater than that found naturally occurring in hydrogen (about 0.016 atom %). In some embodiments, any position in the compound defined as having deuterium 15 has a minimum deuterium incorporation of at least 10 atom %, at least 20 atom %, at least 25 atom %, at least 30 atom %, at least 40 atom %, at least 45 atom %, at least 50 atom %, at least 60 atom %, at least 70 atom %, at least 80 atom %, at least 90 atom %, at least 95 atom %, at least 99 atom % at the site of deuteration. The compounds described herein, e.g., compounds of Formula (I) through (III), may 20 contain a stereogenic center. In such cases, the compounds may exist as different stereoisomeric forms, even though Formula (I) through (III) are drawn without reference to stereochemistry. Accordingly, the present disclosure includes all possible stereoisomers and includes not only racemic compounds but the individual enantiomers (enantiomerically pure compounds), individual diastereomers (diastereomerically pure compounds), and their non-racemic mixtures as 25 well. When a compound is desired as a single enantiomer, such may be obtained by stereospecific synthesis, by resolution of the final product or any convenient intermediate, or by chiral chromatographic methods as each are known in the art. Resolution of the final product, an intermediate, or a starting material may be performed by any suitable method known in the art. In some embodiments, the compounds described herein, e.g., compounds of Formula (I) 30 through (III), are non-stereogenic. In some embodiments, the compounds described herein, e.g., compounds of Formula (I) through (III), are racemic. In some embodiments, the compounds described herein, e.g., compounds of Formula (I) through (III), are enantiomerically enriched (one 107

[0072] enantiomer is present in a higher percentage), including enantiomerically pure. In some embodiments, the compounds described herein, e.g., compounds of Formula (I) through (III), are provided as a single diastereomer. In some embodiments, the compounds described herein, e.g., compounds of Formula (I) through (III), are provided as a mixture of diastereomers. When 5 provided as a mixture of diastereomers, the mixtures may include equal mixtures, or mixtures which are enriched with a particular diastereomer (one diastereomer is present in a higher percentage than another). As described herein, a racemic compound, e.g., a compound of Formula (I) through (III), may contain about 50% of the R- and S-stereoisomers based on a molar ratio (about 48 to about 10 52 mol %, or about a 1:1 ratio)) of one of the isomers. In some embodiments, a pharmaceutical formulation, medicament, or method of treatment may involve combining separately produced compounds of the R- and S-stereoisomers in an approximately equal molar ratio (e.g., about 48 to 52%). In some embodiments, a medicament or pharmaceutical formulation may contain a mixture of separate compounds of the R- and S-stereoisomers in different ratios. In some embodiments, 15 the pharmaceutical formulation contains an excess (greater than 50%) of the R-enantiomer. Suitable molar ratios of R / S may be from about 1.5:1, 2:1, 3:1, 4:1, 5:1, 10:1, or higher. In some embodiments, a pharmaceutical formulation may contain an excess of the S-enantiomer, with the ratios provided for R / S reversed. Other suitable amounts of R / S may be selected. For example, the R-enantiomer may be enriched, e.g., may be present in amounts of at least about 55% to 100%, or 20 at least 65%, at least 75%, at least 80%, at least 85%, at least 90%, about 95%, about 98%, or 100%. In other embodiments, the S-enantiomer may be enriched, e.g., in amounts of at least about 55% to 100%, or at least 65%, at least 75%, at least 80%, at least 85%, at least 90%, about 95%, about 98%, or 100%. Ratios between all these exemplary embodiments as well as greater than and less than them while still within the disclosure, all are included. Pharmaceutical formulations may 25 contain a mixture of the racemate and a separate compound of Formula (I) through (III), in salt form. In some embodiments, the compound of Formula (I) through (III) is an agonist of a serotonin 5-HT2 receptor. In some embodiments, the compound of Formula (I) through (III) is an agonist of a serotonin 5-HT2Areceptor. In some embodiments, the compound of Formula (I) 30 through (III) is an agonist of a serotonin 5-HT1Areceptor. In some embodiments, the compound of Formula (I) through (III) is an agonist of a serotonin 5-HT2C receptor. 108

[0073] In some embodiments, the tryptamine psychedelic used in the preparation of the pharmaceutical formulation is chemically pure, for example has a purity of greater than 90%, 92%, 94%, 96%, 97%, 98%, or 99% by UPLC or HPLC. In some embodiments, the tryptamine psychedelic has no single impurity of greater than 1%, greater than 0.5%, greater than 0.4%, 5 greater than 0.3%, or greater than 0.2%, measured by UPLC or HPLC. In some embodiments, the tryptamine psychedelic has a chemical purity of greater than 97 area %, greater than 98 area %, or greater than 99 area % by UPLC or HPLC. In some embodiments, the tryptamine psychedelic has no single impurity greater than 1 area %, greater than 0.5 area %, greater than 0.4 area %, greater than 0.3 area %, or greater than 0.2 area % as measured by UPLC or HPLC. 10 Acids which may be used to form the pharmaceutically acceptable (acid addition) salts of the compounds disclosed herein, e.g., compounds of Formula (I) through (III), include, but are not limited to, acetic acid, 2,2-dichloroacetic acid, phenylacetic acid, acylated amino acids, alginic acid, ascorbic acid, L-aspartic acid, sulfonic acids (e.g., benzenesulfonic acid, camphorsulfonic acid, (+)-(1S)-camphor-10-sulfonic acid, ethane-1,2-disulfonic acid, ethanesulfonic acid, 2-15 hydroxy-ethanesulfonic acid, methanesulfonic acid, naphthalene-2-sulfonic acid, naphthalene-1,5- disulfonic acid, p-toluenesulfonic acid, ethanedisulfonic acid, etc.), benzoic acids (e.g., benzoic acid, 4-acetamidobenzoic acid, 2-acetoxybenzoic acid, salicylic acid, 4-amino-salicylic acid, gentisic acid, etc.), boric acid, (+)-camphoric acid, cinnamic acid, citric acid, cyclamic acid, cyclohexanesulfamic acid, dodecylsulfuric acid, formic acid, fumaric acid, galactaric acid, 20 glucoheptonic acid, D-gluconic acid, D-glucuronic acid, L-glutamic acid, α-oxo-glutaric acid, glycolic acid, hippuric acid, hydrobromic acid, hydrochloric acid, hydroiodic acid, (+)-L-lactic acid, (−)-D-lactic acid, (±)-DL-lactic acid, lactobionic acid, maleic acid, malic acid, (−)-L-malic acid, (+)-D-malic acid, hydroxymaleic acid, malonic acid, (±)-DL-mandelic acid, isethionic acid, 1-hydroxy-2-naphthoic acid, nicotinic acid, nitric acid, orotic acid, oxalic acid, pamoic acid, 25 perchloric acid, phosphoric acid, L-pyroglutamic acid, saccharic acid, succinic acid, sulfuric acid, sulfamic acid, tannic acid, tartaric acids (e.g., DL-tartaric acid, (+)-L-tartaric acid, (−)-D-tartaric acid), thiocyanic acid, propionic acid, valeric acid, and fatty acids (including fatty mono- and di- acids, e.g., adipic (hexandioic) acid, lauric (dodecanoic) acid, linoleic acid, myristic (tetradecanoic) acid, capric (decanoic) acid, stearic (octadecanoic) acid, oleic acid, caprylic 30 (octanoic) acid, palmitic (hexadecenoic) acid, sebacic acid, undecylenic acid, caproic acid, etc.). Combinations of acids may also be used to form a mixture of acid addition salts. 109

[0074] When the injectable pharmaceutical formulation is prepared from a pre-formed pharmaceutically acceptable salt of a compound disclosed herein, certain salt forms are preferred among the list above because they possess physical and pharmaceutical characteristics / properties which make them well-suited for pharmaceutical preparation and administration. For example, 5 preferred salt forms of the compounds disclosed herein (e.g., compounds of Formula (I) through (III)) are those that possess one or more of the following characteristics: are easy to prepare in high yield with a propensity towards salt formation; are stable and have well-defined physical properties such as crystallinity, lack of polymorphism, and high melting / enthalpy of fusion; have slight or no hygroscopicity; are free flowing, do not cohere / adhere to surfaces, and possess a 10 regular morphology; have acceptable aqueous solubility for the intended route of administration; and / or are physiologically acceptable, e.g., do not cause irritation when administered to mammals. Crystallinity When pre-formed as a solid, the pharmaceutically acceptable salt of the compound of the present disclosure (e.g., a compound of Formula (I) through (III)) may be crystalline or amorphous, 15 preferably crystalline, as determined e.g., by X-ray powder diffraction (XRPD). In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure is amorphous, e.g., as determined by XRPD and / or DSC. The pharmaceutically acceptable salt of the compound of the present disclosure can be in a stable amorphous form. In some embodiments, a highly pure amorphous form of a pharmaceutically acceptable salt of a compound of the present 20 disclosure is provided, wherein at least 92%, at least 94%, at least 96%, at least 98%, at least 99%, or at least 99.5% by weight of the pharmaceutically acceptable salt of the compound of the present disclosure is in amorphous form, e.g., as determined by X-ray powder diffraction and / or DSC. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure is crystalline. Crystalline forms are advantageous in terms of e.g., stability and 25 providing well-defined physical properties, which is desirable for pharmaceutical preparation and administration. The pharmaceutically acceptable salt of the compound of the present disclosure can be in a stable crystalline form. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a percent crystallinity of at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 95%, at least 99%, or at least 99.5%, and up to 100%, 30 as determined by XRPD and / or DSC analysis. In some embodiments, a highly pure crystalline form of a pharmaceutically acceptable salt of a compound of the present disclosure is provided, wherein at least 90%, at least 95%, at least 99%, or at least 99.5% by weight of the 110

[0075] pharmaceutically acceptable salt of the compound of present disclosure is in crystalline form, e.g., as determined by X-ray powder diffraction and / or DSC. Preference is given to those pre-formed salt forms with high crystallinity, as determined e.g., by discrete and sharp Bragg diffractions in the X-ray diffractograms. 5 XRPD analyses can be carried out, e.g., on a Bruker D5000 X-ray powder diffractometer using CuKα radiation (wavelength = 1.54060 Å). The instrument may be equipped with a fine focus X-ray tube. The tube voltage and amperage can be set to 40 kV and 30 mA, respectively. The divergence and scattering slit widths can be set at 2 mm and the detector slit width can be set at 0.2 mm. Diffracted radiation can be detected by a NaI scintillation detector. A theta-two theta 10 continuous scan from 2.0 to 40° (4 seconds per step; 0.01° step size) can be used. In terms of pharmaceutical production processes, advantageous salt forms of the compounds of the present disclosure are those that readily afford a crystalline solid on crystallization in acceptable yield without proceeding via an oil, and with favorable volume factors, making them suitable for mass production. 15 Salts forms of the compound of the present disclosure (e.g., a compound of Formula (I) through (III)) can in some cases exist in different polymorphs (i.e., forms having a different crystal structure), however, preferred salt forms of the present disclosure are those which can be crystallized into a single crystalline form or single polymorph, as determined by XRPD and / or differential scanning calorimetry (DSC). It is also generally desirable for the salt forms to be free 20 flowing, not cohere / adhere to surfaces, and possess a regular morphology. Chemical / Solid-state Stability In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a melt onset of from about 100°C, from about 110°C, from about 120°C, from about 130°C, from about 140°C, from about 150°C, from about 160°C, from about 170°C, from about 25 180°C, from about 190°C, and up to about 250°C, up to about 225°C, up to about 210°C, up to about 200°C, as determined by DSC. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has an enthalpy of fusion of from about 90 J·g-1, from about 100 J·g-1, from about 110 J·g-1, from about 120 J·g-1, from about 130 J·g-1, from about 140 J·g-1, from about 150 J·g-1, from 30 about 160 J·g-1, and up to about 190 J·g-1, up to about 180 J·g-1, up to about 170 J·g-1, as determined by DSC. 111

[0076] Pre-formed pharmaceutically acceptable salts of the compound of the present disclosure suitable for pharmaceutical manufacture may also be characterized as non-hygroscopic or slightly hygroscopic, preferably non-hygroscopic. The hygroscopicity may be measured herein by performing a moisture adsorption-desorption isotherm using a dynamic vapor sorption (DVS) 5 analyzer with a starting exposure of 30% relative humidity (RH), increasing humidity up to 95% RH, decreasing humidity to 0%, and finally increasing the humidity back to the starting 30% RH, and classified according to the following: non-hygroscopic: < 0.2%; slightly hygroscopic: ≥ 0.2% and < 2%; hygroscopic: ≥ 2% and < 15%; very hygroscopic: ≥ 15%; deliquescent: sufficient water is absorbed to form a 10 liquid; all values measured as weight increase (w / w due to acquisition of water) at >95% RH and 25°C. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a weight increase at >95% RH of less than 1% w / w, less than 0.8% w / w, less than 0.6% w / w, less than 0.5% w / w, less than 0.4% w / w, less than 0.3% w / w, less than 0.2% w / w, less 15 than 0.1% w / w, less than 0.08% w / w, less than 0.06% w / w, less than 0.05% w / w, less than 0.02% w / w, as determined by DVS. Pre-formed pharmaceutically acceptable salts of the compounds of the present disclosure can be maintained / stored in open or closed environments, such as in open or closed flasks / vials, under ambient or stress conditions e.g., 25°C / 60% RH, 25°C / 90+% RH, 40°C / 75% RH, etc. 20 without appreciable degradation (e.g., without appreciably diminished chemical purity) or physical changes (e.g., changed forms, deliquesced, etc.). For example, dry powder samples of salt forms disclosed herein may have a purity change or form change of less than 10%, less than 5%, less than 1%, when stored under ambient conditions or stress conditions (e.g., increased temperature, e.g., 40°C, and / or humidity). 25 Physiologically Acceptability Suitable salt forms of the compounds of the present disclosure are physiologically acceptable and do not cause excessive irritation or tissue damage at the injection site. Accordingly, preferred pharmaceutical salts of the compounds of the present disclosure, e.g., compounds of Formula (I) through (III), are those formed with an organic acid, preferably an organic acid with 30 a mild acidity, for example an organic acid with a pKain water of no less than 1.0, no less than 1.5, no less than 2.0, no less than 2.5, no less than 3.0, no less than 3.5, no less than 4.0, no less than 4.5, for example, from 3.0 to 6.5. 112

[0077] Solubility The aqueous solubility of the pharmaceutical salts of the compounds of the present disclosure can be determined by equilibrating excess solid with 1 mL of water for 24 hours at 22° C. A 200 uL aliquot can be centrifuged at 15,000 revolutions per minute (rpm) for 15 minutes. 5 The supernatant can be analyzed by UPLC or HPLC and the solubility can be expressed as its free base equivalent (mg FB / mL). For example, pharmaceutically acceptable salt forms of the compounds of the present disclosure can be prepared and the solubility and solution pH can be measured. In some embodiments, the pharmaceutically acceptable salt of the compound of the present 10 disclosure, e.g., a compound of Formula (I) through (III), has a water solubility at 22°C of from about 5 mg / mL to about 400 mg / mL. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a water solubility of from about 1 mg / mL, from about 2 mg / mL, from about 3 mg / mL, from about 5 mg / mL, from about 10 mg / mL, from about 20 mg / mL, from about 30 mg / mL, from about 40 mg / mL, from about 50 mg / mL, from about 60 15 mg / mL, from about 70 mg / mL, from about 80 mg / mL, from about 90 mg / mL, from about 100 mg / mL, from about 110 mg / mL, from about 120 mg / mL, from about 130 mg / mL, from about 140 mg / mL, from about 150 mg / mL, and up to about 400 mg / mL, up to about 380 mg / mL, up to about 360 mg / mL, up to about 340 mg / mL, up to about 320 mg / mL, up to about 300 mg / mL, up to about 280 mg / mL, up to about 260 mg / mL, up to about 250 mg / mL, or any range therebetween. In some 20 embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a water solubility from about 200 mg / mL to about 400 mg / mL. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a water solubility from about 150 mg / mL to about 250 mg / mL. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure has a 25 water solubility of greater than about 1 mg / mL, 10 mg / mL, 20 mg / mL, 30 mg / mL, 40 mg / mL, 50 mg / mL, 60 mg / mL, 70 mg / mL, 80 mg / mL, 90 mg / mL, 100 mg / mL, 110 mg / mL, 120 mg / mL, 130 mg / mL, 140 mg / mL, or 150 mg / mL. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure, e.g., the compound of Formula (I) through (III), is a fumarate, a benzoate, a salicylate, 30 a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt. In terms of providing desirable physical and pharmaceutical characteristics, such as those described above, preferred pharmaceutically acceptable salts are fumarate salts, hemi-fumarate salts, benzoate salts, 113

[0078] salicylates, and succinate salts of the compounds disclosed herein, e.g., the compounds of Formula (I) through (III), with fumarate, benzoate, and salicylate salts being particularly preferred. In some embodiments, the pharmaceutically acceptable salt of the compound of the present disclosure, e.g., the compound of Formula (I) through (III), is a benzenesulfonate salt. 5 In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt of N,N- dimethyltryptamine (DMT). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi- fumarate salt of 5-hydroxy-N,N-dimethyltryptamine (5-OH-DMT). In some embodiments, the 10 pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt of 5-methoxy-N,N-dimethyltryptamine (5-MeO- DMT). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt of 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (DMT-d10). In some embodiments, the 15 pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1-d2 (a DMT-d8). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi- fumarate salt of a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1- 20 amine-1,1-d2(a DMT-d2). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi- fumarate salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(5- MeO-DMT-d10). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt 25 of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2 (5-MeO-DMT-d5). In some embodiments, the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi-oxalate, or a hemi-fumarate salt of 2-(5-(methoxy-d3)- 1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (5-MeO-DMT-d13). In some embodiments, the pharmaceutically acceptable salt of DMT or a deuterated analog 30 of DMT (e.g., DMT-d10) is a crystalline solid as disclosed in PCT / EP2023 / 050702, which is incorporated herein by reference in its entirety. 114 Non-limiting examples of pharmaceutically acceptable salts of compounds of Formula (I) and (II) are provided in Table 1. Table 1. Exemplary pharmaceutically acceptable salts of compounds of Formula (I) / (II) 5 In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a fumarate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1a) (i.e., a fumarate salt of compound I-1, depicted below). In some embodiments, when salt I-1a is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 7.8°, 10.3°, 10.9°, 13.6°, 10 15.8°, 16.1°, 17.0°, 18.4°, 19.7°, 19.9°, 20.6°, 21.3°, 21.7°, 22.5°, 23.9°, 24.1°, 25.1°, 26.2°, 33.6°, and 34.9°, as determined by XRPD using a CuKα radiation source. 115

[0079] In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a benzoate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1b) (i.e., a 5 benzoate salt of compound I-1 depicted above). In some embodiments, when salt I-1b is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 11.1°, 12.6°, 13.5°, 15.8°, 16.1°, 17.1°, 17.9°, 19.8°, 20.1°, 20.8°, 21.2°, 22.7°, 23.8°, 24.6°, 26.9°, 29.2°, 32.3°, 35.1°, and 36.1°, as determined by XRPD using a CuKα radiation source. 10 In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a salicylate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1c) (i.e., a salicylate salt of compound I-1 depicted above). In some embodiments, when salt I-1c is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 10.5°, 14.9°, 17.1°, 15 18.1°, 19.1°, 20.1°, 20.7°, 21.0°, 21.3°, 24.6°, 25.6°, 28.5°, 28.8°, 29.4°, 30.3°, 31.3°, 32.1°, 33.5°, and 34.4°, as determined by XRPD using a CuKα radiation source. In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a succinate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1d) (i.e., a succinate salt of compound I-1 depicted above). In some embodiments, when salt I-1d is in a 20 crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.8°, 11.7°, 14.3°, 14.7°, 17.0°, 17.4°, 19.6°, 20.6°, 22.3°, 22.6°, 22.9°, 23.1°, 23.4°, 24.9°, 25.2°, 26.3°, 26.8°, 27.3°, 27.7°, 28.8°, 29.1°, 30.9°, 31.5°, 33.8°, 34.5°, 36.5°, and 39.2°, as determined by XRPD using a CuKα radiation source. 25 In some embodiments, the pharmaceutically acceptable salt of a compound of the present 116

[0080] disclosure is an oxalate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1e) (i.e., an oxalate salt of compound I-1 depicted above). In some embodiments, when salt I-1e is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 11.3°, 12.3°, 15.6°, 17.7°, 5 19.5°, 20.0°, 20.8°, 21.4°, 22.3°, 22.7°, 24.8°, 25.7°, 26.7°, 27.9°, 28.7°, 29.5°, 31.4°, 33.0°, 35.4°, 36.5°, and 38.6°, as determined by XRPD using a CuKα radiation source. In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a glycolate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1f) (i.e., a glycolate salt of compound I-1 depicted above). In some embodiments, when salt I-1f is in a 10 crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 8.2°, 12.2°, 12.9°, 15.8°, 16.3°, 17.8°, 19.2°, 20.1°, 21.7°, 23.6°, 24.4°, 24.6°, 24.9°, 26.0°, 26.6°, 27.8°, 29.6°, 30.2°, 32.0°, 32.3°, 33.0°, 33.9°, and 34.6°, as determined by XRPD using a CuKα radiation source. In some embodiments, the pharmaceutically acceptable salt of a compound of the present 15 disclosure is a hemi-oxalate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1g) (i.e., a hemi-oxalate salt of compound I-1 depicted above). In some embodiments, when salt I-1g is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 8.7°, 11.5°, 13.6°, 14.2°, 15.2°, 17.4°, 17.6°, 18.0°, 19.3°, 19.6°, 20.1°, 20.6°, 21.9°, 22.1°, 22.9°, 23.2°, 23.5°, 24.5°, 25.0°, 20 25.5°, 26.1°, 26.4°, 27.1°, 28.4°, 28.7°, 29.8°, 30.4°, 30.7°, 31.4°, 31.8°, 33.4°, and 33.9°, as determined by XRPD using a CuKα radiation source. In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a hemi-fumarate salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-1h) (i.e., a hemi-fumarate salt of compound I-1 depicted above). In some embodiments, when salt I-1h is in 25 a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 8.1°, 11.3°, 12.2°, 13.3°, 14.2°, 16.2°, 17.6°, 18.3°, 18.6°, 19.5°, 19.8°, 20.0°, 20.2°, 20.9°, 21.4°, 21.9°, 22.3°, 22.7°, 22.9°, 23.8°, 24.5°, 25.0°, 25.2°, 26.1°, 26.4°, 26.9°, 28.4°, 28.8°, 29.5°, 29.8°, 30.9°, and 32.7°, as determined by XRPD using a CuKα radiation source. 30 In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a fumarate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I- 8a) (i.e., a fumarate salt of compound I-8 depicted below). In some embodiments, when salt I-8a 117 is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 7.8°, 10.3°, 10.9°, 12.5°, 13.6°, 14.6°, 15.2°, 15.5°, 15.8°, 16.1°, 16.6°, 17.0°, 18.4°, 19.0°, 19.7°, 19.9°, 20.6°, 21.3°, 21.8°, 22.5°, 23.3°, 23.8°, 24.1°, 25.1°, 26.2°, 26.8°, 27.3°, 27.9°, 28.3°, 28.9°, 29.3°, 29.6°, 29.9°, 5 30.6°, 31.0°, 31.3°, 32.4°, 32.9°, 33.3°, 33.6°, 34.3°, 34.9°, 35.7°, 36.1°, 37.4°, 38.0°, and 38.5°, as determined by XRPD using a CuKα radiation source. In some embodiments, when salt I-8a is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 7.8°, 10.3°, 10.9°, 13.6°, 15.8°, 16.1°, 17.0°, 18.4°, 19.7°, 19.9°, 20.6°, 21.3°, 21.8°, 22.5°, 23.8°, 24.1°, 25.1°, 26.2°, 10 33.6°, and 34.9°, as determined by XRPD using a CuKα radiation source. In some embodiments, when salt I-8a is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 10.9°, 13.6°, 15.8°, 16.1°, 17.0°, 18.4°, 19.7°, 19.9°, 20.6°, 23.8°, 24.1°, and 25.1°, as determined by XRPD using a CuKα radiation source. 15 In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a benzoate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I- 8b) (i.e., a benzoate salt of compound I-8 depicted above). In some embodiments, when salt I-8b 20 is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 11.1°, 12.7°, 13.5°, 15.8°, 16.1°, 17.2°, 17.9°, 19.8°, 20.1°, 20.8°, 21.2°, 22.8°, 23.8°, 24.3°, 24.6°, 25.1°, 25.3°, 25.5°, 26.9°, 28.3°, 28.9°, 29.3°, 31.4°, 31.6°, 32.0°, 32.3°, 32.8°, 35.1°, and 36.1°, as determined by XRPD using a CuKα radiation source. In some embodiments, when salt I-8b is in a crystalline 25 solid form it is characterized by an X-ray powder diffraction pattern containing at least three 118

[0081] characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 11.1°, 12.7°, 13.5°, 15.8°, 16.1°, 17.2°, 17.9°, 19.8°, 20.1°, 20.8°, 21.2°, 22.8°, 23.8°, 24.6°, 26.9°, 29.3°, 32.3°, 35.1°, and 36.1°, as determined by XRPD using a CuKα radiation source. In some embodiments, when salt I-8b is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern 5 containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 12.7°, 13.5°, 15.8°, 16.1°, 17.2°, 17.9°, 19.8°, 20.1°, 20.8°, 23.8°, 24.6°, 26.9°, 29.3°, and 35.1° as determined by XRPD using a CuKα radiation source. In some embodiments, the pharmaceutically acceptable salt of a compound of the present disclosure is a salicylate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I- 10 8c) (i.e., a salicylate salt of compound I-8 depicted above). In some embodiments, when salt I-8c is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 10.5°, 11.4°, 12.3°, 13.4°, 14.2°, 14.9°, 15.6°, 16.1°, 17.1°, 18.1°, 18.7°, 19.1°, 20.1°, 20.8°, 21.1°, 21.3°, 22.2°, 22.6°, 23.7°, 24.6°, 25.2°, 25.6°, 26.1°, 26.4°, 27.4°, 27.5°, 27.8°, 28.5°, 28.8°, 29.4°, 29.7°, 30.3°, 15 31.0°, 31.3°, 32.1°, 32.7°, 33.1°, 33.5°, 34.4°, and 35.0°, as determined by XRPD using a CuKα radiation source. In some embodiments, when salt I-8c is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 10.5°, 14.9°, 17.1°, 18.1°, 19.1°, 20.1°, 20.8°, 21.1°, 21.3°, 24.6°, 25.6°, 28.5°, 28.8°, 29.4°, 30.3°, 31.3°, 32.1°, 33.5°, and 34.4°, as determined 20 by XRPD using a CuKα radiation source. In some embodiments, when salt I-8c is in a crystalline solid form it is characterized by an X-ray powder diffraction pattern containing at least three characteristic peaks at diffraction angles (2θ ± 0.2°) selected from 9.6°, 14.9°, 17.1°, 18.1°, 19.1°, 20.1°, 20.8°, 21.3°, 24.6°, 25.6°, 28.5°, and 32.1°, as determined by XRPD using a CuKα radiation source. 25 Non-limiting examples of pharmaceutically acceptable salts of compounds of Formula (I) and (III) are provided in Table 2. 119 Table 2. Exemplary pharmaceutically acceptable salts of compounds of Formula (I) / (III) 120 Table 2. (continued) In some embodiments, the pharmaceutically acceptable salt is hydrochloride salt of N,N- dimethyltryptamine (DMT). In some embodiments, the pharmaceutically acceptable salt is a 5 hydrochloride salt of 5-hydroxy-N,N-dimethyltryptamine (5-OH-DMT). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(DMT-d10). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 2-(1H-indol-3-yl)- 10 N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (a DMT-d8). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 2-(1H-indol-3-yl)-N,N-dimethylethan- 1-amine-1,1-d2(a DMT-d2). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (5-MeO-DMT-d10). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride 15 salt of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2(5-MeO-DMT-d5). In some embodiments, the pharmaceutically acceptable salt is a hydrochloride salt of 2-(5- (methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (5-MeO-DMT-d13). Various methods and procedures may be used to prepare pre-formed pharmaceutically acceptable salts of the compounds of the present disclosure, such methods and procedures being 20 generally known to those of ordinary skill in the art. In some embodiments, the pre-formed pharmaceutically acceptable salt of a compound of the present disclosure is prepared by: (a) suspending or dissolving a free base of the compound of the present disclosure (e.g., a compound of Formula (I) through (III) in a solvent or mixture of solvents; (b) contacting an acid with the compound of the present disclosure to provide a mixture; 25 (c) optionally heating the mixture; (d) optionally cooling the mixture; and (e) isolating the salt. 121

[0082] Various solvents may be used, including one or more protic solvents, one or more aprotic solvents, or mixtures thereof. In some embodiments, the solvent(s) is a protic solvent(s). In some embodiments, the solvent is selected from the group consisting of methanol, ethanol, propanol, isopropanol, butanol, 2-butanol, acetone, butanone, dioxanes (1,4-dioxane), water, tetrahydrofuran 5 (THF), acetonitrile (MeCN), ether solvents (e.g., t-butylmethyl ether (TBME)), hexane, heptane, and octane, and combinations thereof. In some embodiments, the solvent is ethanol. Suitable acids for use during the contacting step may include those described heretofore. The acid may be an inorganic acid (e.g., hydrochloric acid) or an organic acid, with organic acids being preferred. In some embodiments, the acid is an organic acid selected from the group 10 consisting of fumaric acid, benzoic acid, salicylic acid, succinic acid, oxalic acid, and glycolic acid. In some embodiments, the acid is an organic acid selected from the group consisting of fumaric acid, benzoic acid, salicylic acid, and succinic acid, with fumaric acid, benzoic acid, and salicylic acid being preferred. In some embodiments, a stoichiometric (or superstoichiometric) quantity of the acid is contacted with the compound of the present disclosure. In some 15 embodiments, a sub-stoichiometric (e.g., 0.5 molar equivalents) quantity of the acid is contacted with the compound of the present disclosure. The use of sub-stoichiometric quantities of the acid may be desirable when, for example, the acid contains at least two acidic protons (e.g., two or more carboxylic acid groups) and the target salt is a hemi-acid salt. In some embodiments, the mixture is heated, e.g., refluxed, prior to cooling. 20 In some embodiments, the mixture is cooled and the salt is precipitated out of the solution. In some embodiments, the salt is precipitated out of solution in crystalline form. In some embodiments, the salt is precipitated out of solution in amorphous form. Isolation of the salt may be performed by various well-known isolation techniques, such as filtration, decantation, and the like. In some embodiments, the isolating step includes filtering 25 the mixture. After isolation, additional crystallization and / or recrystallization steps may also optionally be performed, if desired, for example to increase purity, crystallinity, etc. Active salt mixture The pharmaceutical formulation may comprise, as the psychopharmaceutical agent, a 30 pharmaceutically acceptable salt of a single compound of the present disclosure (e.g., a single of compound of Formula (I) through (III)) or a pharmaceutically acceptable salt of a mixture of compounds of the present disclosure (e.g., a mixture of compounds of Formula (I) through (III)). 122

[0083] In one example, the pharmaceutical formulation may contain an isotopologue mixture of compounds of the present disclosure in salt form as the psychopharmaceutical agent. In some embodiments, a subject compound of Formula (I) through (III) in salt form may be present in the pharmaceutical formulation at a purity of at least 20% by weight, at least 30% by weight, at least 5 40% by weight, at least 50% by weight, at least 60% by weight, at least 70% by weight, at least 80% by weight, at least 90% by weight, at least 95% by weight, at least 99% by weight, based on a total weight of the isotopologue mixture of compounds of Formula (I) through (III) in salt form present in the pharmaceutical formulation. For example, a pharmaceutical formulation formulated with a DMT-d10salt (salt form of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4), 10 as the subject compound in salt form, may additionally contain isotopologues of the subject compound in salt form, e.g., DMT-d9 salt, a DMT-d8 salt, etc. In some embodiments, the pharmaceutical formulation is substantially free of other isotopologues of the subject compound in salt form, e.g., the pharmaceutical formulation has less than 20, 15, 10, 9, 8, 7, 6, 5, 4, 3, 2 or 1 or 0.5 mole percent of other isotopologues of the subject compound in salt form. 15 When the injectable pharmaceutical formulation comprises, as the psychopharmaceutical agent, a pharmaceutically acceptable salt of a mixture of compounds of the present disclosure (e.g., a mixture of compounds of Formula (I) through (III)), that mixture may be referred to herein an “active salt mixture”. In some embodiments, the active salt mixture is a fumarate salt mixture, wherein the salt forms recited are fumarate salts. In some embodiments, the active salt mixture is 20 a benzoate salt mixture, wherein the salt forms recited are benzoate salts. In some embodiments, the active salt mixture is a salicylate salt mixture, wherein the salt forms recited are salicylate salts. In some embodiments, the active salt mixture is a succinate salt mixture, wherein the salt forms recited are succinate salts. In some embodiments, the pharmaceutical formulation comprises an active salt mixture 25 comprising: (i) a pharmaceutically acceptable salt of DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8); (ii) a pharmaceutically acceptable salt of DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11); and optionally (iii) a pharmaceutically30 acceptable salt of DMT-d8, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-2,2-d2(I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12). In123

[0084] some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt 5 mixture, of (i) a pharmaceutically acceptable salt of DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 10 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by 15 weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a pharmaceutically acceptable salt of DMT-d8, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I- 6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2(I-7), and / or 2-(1H-indol-3-yl)- 20 N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12). In some embodiments, the active salt mixture consists of or consists essentially of (i) a pharmaceutically acceptable salt of DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4(I-8); and (ii) a pharmaceutically acceptable salt of DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 25 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) from 90% to 99% by weight of a pharmaceutically acceptable salt of DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine- 1,1,2,2-d4(I-8), or any range therebetween, based on a total weight of the active salt mixture; and 30 (ii) from 1% to 10% by weight, in sum, of a pharmaceutically acceptable salt of DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,2,2-d3(I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11),124

[0085] or any range therebetween, based on a total weight of the active salt mixture. In some embodiments, the active salt mixture (and thus the pharmaceutical formulation) contains no detectable amount of, or is otherwise substantially free of: (1) a pharmaceutically acceptable salt of DMT-d8, i.e., a pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N- 5 bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine- 2,2-d2(I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12); (2) a pharmaceutically acceptable salt of DMT-d7; (3) a pharmaceutically acceptable salt of DMT-d6 (a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine (I-4)); (4) a pharmaceutically acceptable salt of DMT-d5; (5) a pharmaceutically acceptable salt of DMT- 10 d4 (a salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1,2,2-d4 (I-5)); (6) a pharmaceutically acceptable salt of DMT-d3; (7) a pharmaceutically acceptable salt of DMT-d2 (a salt of one or more of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2(I-2) and / or 2-(1H- indol-3-yl)-N,N-dimethylethan-1-amine-2,2-d2(I-3)); (8) a pharmaceutically acceptable salt of DMT-d1; and (9) a pharmaceutically acceptable salt of DMT (a salt of 2-(1H-indol-3-yl)-N,N- 15 dimethylethan-1-amine (I-1)). For example, in some embodiments, a weight, in sum, of pharmaceutically acceptable salts of isotopologues of DMT not listed in (i) or (ii), such as those listed in (1) through (9), is less than 1% by weight, less than 0.75% by weight, less than 0.5% by weight, less than 0.4% by weight, less than 0.3% by weight, less than 0.25% by weight, less than 0.2% by weight, less than 0.1% by weight, or 0% by weight, based on a total weight of the active 20 salt mixture. In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a fumarate salt of DMT-d10, i.e., a fumarate salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8); (ii) a fumarate salt of DMT-d9, i.e., a fumarate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2- 25 (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11); and optionally (iii) a fumarate salt of DMT-d8, i.e., a fumarate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2 (I-7), and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 30 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a fumarate salt 125

[0086] of DMT-d10, i.e., a fumarate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4(I-8). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% 5 by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a fumarate salt of DMT-d9, i.e., a fumarate salt of one or more of 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less 10 than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a fumarate salt of DMT-d8, i.e., a fumarate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2(I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-2,2-d2 (I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In 15 some embodiments, the active salt mixture consists of or consists essentially of (i) a fumarate salt of DMT-d10, i.e., a fumarate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4 (I-8); and (ii) a fumarate salt of DMT-d9, i.e., a fumarate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1,2-d3(I-11). 20 In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a benzoate salt of DMT-d10, i.e., a benzoate salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8); (ii) a benzoate salt of DMT-d9, i.e., a benzoate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11); and optionally (iii) a benzoate25 salt of DMT-d8, i.e., a benzoate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1-d2(I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2(I-7), and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by 30 weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a benzoate salt of DMT-d10, i.e., a benzoate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-126

[0087] d4 (I-8). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the 5 active salt mixture, of (ii) a benzoate salt of DMT-d9, i.e., a benzoate salt of one or more of 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, 10 less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a benzoate salt of DMT-d8, i.e., a benzoate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2(I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-2,2-d2(I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12). In some embodiments, the active salt mixture consists of or consists essentially of (i) a benzoate salt15 of DMT-d10, i.e., a benzoate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4(I-8); and (ii) a benzoate salt of DMT-d9, i.e., a benzoate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the pharmaceutical formulation comprises an active salt mixture20 comprising: (i) a salicylate salt of DMT-d10, i.e., a salicylate salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I-8); (ii) a salicylate salt of DMT-d9, i.e., a salicylate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11); and optionally (iii) a salicylate salt of DMT-d8, i.e., a salicylate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-25 1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2 (I-7), and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, 30 or any range therebetween, based on a total weight of the active salt mixture, of (i) a salicylate salt of DMT-d10, i.e., a salicylate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4(I-8). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by127

[0088] weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a salicylate salt of DMT-d9, i.e., a salicylate salt of one or more of 2- 5 (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt10 mixture, of (iii) a salicylate salt of DMT-d8, i.e., a salicylate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-2,2-d2(I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-12). In some embodiments, the active salt mixture consists of or consists essentially of (i) a salicylate salt of DMT-d10, i.e., a salicylate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-15 d4 (I-8); and (ii) a salicylate salt of DMT-d9, i.e., a salicylate salt of one or more of 2-(1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a succinate salt of DMT-d10, i.e., a succinate salt of 2-(1H-indol-3-yl)-N,N- 20 bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8); (ii) a succinate salt of DMT-d9, i.e., a succinate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11); and optionally (iii) a succinate salt of DMT-d8, i.e., a succinate salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2 (I-7), and / or 2- 25 (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a succinate salt30 of DMT-d10, i.e., a succinate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4 (I-8). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 128

[0089] 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a succinate salt of DMT-d9, i.e., a succinate salt of one or more of 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N- 5 bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-11). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a succinate salt of DMT-d8, i.e., a succinate salt of one or more of 2-(1H-indol-3-10 yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6), 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-2,2-d2 (I-7), and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-12). In some embodiments, the active salt mixture consists of or consists essentially of (i) a succinate salt of DMT-d10, i.e., a succinate salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2- d4 (I-8); and (ii) a succinate salt of DMT-d9, i.e., a succinate salt of one or more of 2-(1H-indol-3-15 yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-1,1,2-d3(I-11). In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1-d2(I-6); (ii) a pharmaceutically acceptable salt of DMT-d7, i.e., a pharmaceutically 20 acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1-d; and optionally (iii) a pharmaceutically acceptable salt of DMT-d6, i.e., a pharmaceutically acceptable salt of 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine (I-4). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% 25 to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6). In some embodiments, the active salt mixture comprises from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 30 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of DMT-d7, i.e., a pharmaceutically acceptable salt of 2-(1H- 129

[0090] indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1-d. In some embodiments, the active salt mixture comprises from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of 5 (iii) a pharmaceutically acceptable salt of DMT-d6, i.e., a pharmaceutically acceptable salt of 2- (1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine (I-4). In some embodiments, the active salt mixture consists of or consists essentially of (i) a pharmaceutically acceptable salt of 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6); and (ii) a pharmaceutically acceptable salt of DMT-d7, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- 10 amine-1-d. In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1- amine-1,1-d2(I-2); (ii) a pharmaceutically acceptable salt of DMT-d1, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine-1-d; and optionally (iii) a15 pharmaceutically acceptable salt of DMT, i.e., a pharmaceutically acceptable salt of 2-(1H-indol- 3-yl)-N,N-dimethylethan-1-amine. In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween,20 based on a total weight of the active salt mixture, of (i) a pharmaceutically acceptable salt of 2- (1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2 (I-2). In some embodiments, the active salt mixture comprises from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range 25 therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of DMT-d1, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- dimethylethan-1-amine-1-d. In some embodiments, the active salt mixture comprises from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any 30 range therebetween, based on a total weight of the active salt mixture, of (iii) a pharmaceutically acceptable salt of DMT, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- dimethylethan-1-amine. In some embodiments, the active salt mixture consists of or consists 130

[0091] essentially of (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1- amine-1,1-d2(I-2); and (ii) a pharmaceutically acceptable salt of DMT-d1, i.e., a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-dimethylethan-1-amine-1-d. In some embodiments, the pharmaceutical formulation comprises an active salt mixture 5 comprising: (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I- 20); (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I- 22) and / or 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-23); and 10 optionally (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d8, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine- 1,1-d2(I-18), 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2(I-19), and 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-24). In some embodiments, the active salt mixture comprises from 60% to 99% by weight, from 60% to 98% 15 by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-20). In some 20 embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d9, i.e., a pharmaceutically acceptable25 salt of one or more of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I- 22) and / or 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-23). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based30 on a total weight of the active salt mixture, of (iii) a pharmaceutically acceptable salt of 5-MeO- DMT-d8, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol-3-yl)- N,N-bis(methyl-d3)ethan-1-amine-1,1-d2(I-18), 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-131

[0092] d3)ethan-1-amine-2,2-d2 (I-19), and 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,2-d2(I-24). In some embodiments, the active salt mixture (and thus the pharmaceutical formulation) contains no detectable amount of, or is otherwise substantially free of (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d8, i.e., a pharmaceutically acceptable salt of 5 one or more of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2 (I-18), 2- (5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2(I-19), and 2-(5-methoxy- 1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2 (I-24). In some embodiments, the active salt mixture consists of or consists essentially of (i) a pharmaceutically acceptable salt of 5-MeO- DMT-d10, i.e., a pharmaceutically acceptable salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-10 bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I-20); and (ii) a pharmaceutically acceptable salt of 5- MeO-DMT-d9, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-22) and / or 2-(5-methoxy-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-23). In some embodiments, the pharmaceutical formulation comprises an active salt mixture 15 comprising: (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d13, i.e., a pharmaceutically acceptable salt of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-34); (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d12, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,2,2-d3(I-36) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- 20 amine-1,1,2-d3(I-37); and optionally (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d11, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1-d2(I-32), 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl- d3)ethan-1-amine-2,2-d2(I-33), and 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,2-d2 (I-38). In some embodiments, the active salt mixture comprises from 60% to 99% 25 by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d13, i.e., a pharmaceutically acceptable salt of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 30 1-amine-1,1,2,2-d4(I-34). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, 132

[0093] from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of 5-MeO-DMT- d12, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)- N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-36) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- 5 bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-37). In some embodiments, the active salt mixture comprises, in sum, from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d11, i.e., a pharmaceutically10 acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,1-d2 (I-32), 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2 (I-33), and 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2-d2(I-38). In some embodiments, the active salt mixture (and thus the pharmaceutical formulation) contains no detectable amount of, or is otherwise substantially free of (iii) a pharmaceutically acceptable salt15 of 5-MeO-DMT-d11, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)- 1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1-d2(I-32), 2-(5-(methoxy-d3)-1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-2,2-d2 (I-33), and 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,2-d2 (I-38). In some embodiments, the active salt mixture consists of or consists essentially of (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d13, i.e., a20 pharmaceutically acceptable salt of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan- 1-amine-1,1,2,2-d4 (I-34); and (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d12, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-36) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3 (I-37). 25 In some embodiments, the pharmaceutical formulation comprises an active salt mixture comprising: (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d5, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine- 1,1-d2 (I-28) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-2,2-d2 (I-29); (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d4, i.e., a pharmaceutically acceptable salt 30 of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1-d (I-26) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-2-d (I-27); and optionally (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d3, i.e., a pharmaceutically acceptable salt 133

[0094] of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-25). In some embodiments, the active salt mixture comprises, in sum, from 60% to 99% by weight, from 60% to 98% by weight, from 65% to 97% by weight, from 70% to 96% by weight, from 75% to 95% by weight, from 80% to 94% by weight, from 85% to 93% by weight, from 90% to 92% by weight, from 90% 5 to 99% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (i) a pharmaceutically acceptable salt of 5-MeO-DMT-d5, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2 (I- 28) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-2,2-d2 (I-29). In some embodiments, the active salt mixture comprises, in sum, from 1% to 40% by weight, from 2% to 10 40% by weight, from 3% to 35% by weight, from 4% to 30% by weight, from 5% to 25% by weight, from 6% to 20% by weight, from 7% to 15% by weight, from 8% to 10% by weight, from 1% to 10% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (ii) a pharmaceutically acceptable salt of 5-MeO-DMT-d4, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-1-d (I-26) 15 and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine-2-d (I-27). In some embodiments, the active salt mixture comprises from 0% by weight to less than 10% by weight, less than 5% by weight, less than 3% by weight, less than 2% by weight, less than 1% by weight, less than 0.5% by weight, less than 0.25% by weight, or any range therebetween, based on a total weight of the active salt mixture, of (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d3,20 i.e., a pharmaceutically acceptable salt of 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan- 1-amine (I-25). In some embodiments, the active salt mixture (and thus the pharmaceutical formulation) contains no detectable amount of, or is otherwise substantially free of (iii) a pharmaceutically acceptable salt of 5-MeO-DMT-d3, i.e., a pharmaceutically acceptable salt of 2- (5-(methoxy-d3)-1H-indol-3-yl)-N,N-dimethylethan-1-amine (I-25). In some embodiments, the25 active salt mixture consists of or consists essentially of (i) a pharmaceutically acceptable salt of 5- MeO-DMT-d5, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H- indol-3-yl)-N,N-dimethylethan-1-amine-1,1-d2 (I-28) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)- N,N-dimethylethan-1-amine-2,2-d2 (I-29); and (ii) a pharmaceutically acceptable salt of 5-MeO- DMT-d4, i.e., a pharmaceutically acceptable salt of one or more of 2-(5-(methoxy-d3)-1H-indol-3-30 yl)-N,N-dimethylethan-1-amine-1-d (I-26) and / or 2-(5-(methoxy-d3)-1H-indol-3-yl)-N,N- dimethylethan-1-amine-2-d (I-27). Psychopharmaceutical agent content 134

[0095] For use in the treatment of a disease or disorder disclosed herein, namely a neuropsychiatric disease or disorder or an inflammatory disease or disorder, such as a central nervous system (CNS) disorder and / or psychological disorder, including those associated with a 5-HT2receptor, the pharmaceutical formulation comprises a therapeutically effective amount of the 5 psychopharmaceutical agent. In terms of unit dose, the pharmaceutical formulation comprising the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of the compound of Formula (I) through (III)) typically contains a free base dose (free base equivalence when a salt form is used) of about 1 mg, about 2 mg, about 3 mg, about 5 mg, about 10 mg, about 12 mg, about 14 mg, about 16 mg, about 18 mg, about 20 mg, about 25 mg, about 10 30 mg, about 40 mg, about 50 mg, about 75 mg, about 100 mg, about 150 mg, about 200 mg, about 300 mg, or any range therebetween. For example, a pharmaceutical formulation prepared with 40.4 mg of DMT fumarate (molar mass of 304.34 g / mol) would have a free base equivalence of DMT (molar mass of 188.27 g / mol) of about 25 mg as the unit dose. The pharmaceutical formulation can, if desired, also contain other compatible therapeutic agents. 15 The pharmaceutical formulations may have a free base concentration of psychopharmaceutical agent, e.g., a free base concentration of a compound of Formula (I) through (III) (free base equivalence when a salt form is used), by weight per total volume of pharmaceutical formulation of about 1 mg / mL, about 2 mg / mL, about 4 mg / mL, about 6 mg / mL, about 8 mg / mL, about 10 mg / mL, about 12 mg / mL, about 15 mg / mL, about 18 mg / mL, about 20 mg / mL, about 22 20 mg / mL, about 25 mg / mL, about 28 mg / mL, about 30 mg / mL, about 32 mg / mL, about 35 mg / mL, about 40 mg / mL, about 45 mg / mL, about 50 mg / mL, about 55 mg / mL, about 60 mg / mL, about 65 mg / mL, about 70 mg / mL, about 75 mg / mL, about 80 mg / mL, about 85 mg / mL, about 90 mg / mL, about 95 mg / mL, about 100 mg / mL, or any range therebetween, such as from about 5 mg / mL to about 70 mg / mL, from about 10 mg / mL to about 50 mg / mL, from about 15 mg / mL to about 40 25 mg / mL, from about 20 mg / mL to about 35 mg / mL. For example, a pharmaceutical formulation prepared from 40.4 mg of DMT fumarate (molar mass of 304.34 g / mol) in 1 mL of total volume of pharmaceutical formulation would have a free base concentration of psychopharmaceutical agent (in this example DMT free base; molar mass of 188.27 g / mol), of about 25 mg / mL. Of these concentrations, free base concentrations of psychopharmaceutical agent below about 70 mg / mL 30 provide advantageous controlled-release profiles across the broadest range of release modifier molecular weight and release modifier concentrations. However, difficulties with the pharmaceutical formulation may be encountered at free base concentrations of about 70 mg / mL 135

[0096] or higher. Firstly, to achieve the targeted controlled-release effects at these higher free base concentrations, it may be necessary to correspondingly increase the concentration of release modifier. Pushing the limits of the release modifier concentration may be problematic as the higher viscosities thus obtained may complicate or preclude the use of sterile filtration (which in the case 5 of pharmaceutical formulations containing hyaluronate salts is effectively the only suitable sterilization technique available) and may cause increased pain at the injection site. Secondly, a deterioration of pharmaceutical formulation stability may be experienced at the higher free base concentrations of about 70 mg / mL or more, with precipitation being a main concern owing to the pharmacopeial requirements for particulate matter in injectables such as subcutaneous dosage 10 forms (USP Particulate Matter in Injections <788>). Attempts to lower the free base concentration by dilution (increasing injection volume) may not be possible in subcutaneous dosage forms, for example, since higher injection volumes, especially those above 3 mL, are associated with pain at the injection site. Consequently, for subcutaneous pharmaceutical formulations, the free base concentration of psychopharmaceutical agent (e.g., tryptamine psychedelic such as a compound 15 of Formula (I) through (III)) is typically kept below about 70 mg / mL, below about 65 mg / mL, below about 60 mg / mL, below about 55 mg / mL, with 10 to 50 mg / mL being preferred. In terms of pharmaceutical formulations containing a tryptamine psychedelic, it is for these reasons that tryptamine psychedelics with longer half-lives, such as deuterated tryptamine psychedelics may provide significant advantages over their non-deuterated counterparts, 20 especially in subcutaneous dosage forms. Specifically deuterated tryptamine psychedelics possess advantageous metabolic degradation profiles which can lead to higher plasma concentrations and enhanced brain penetration, so that in some embodiments the therapeutic doses may be reduced. For example, initial human clinical studies indicate that a therapeutically relevant psychedelic dose of DMT (non-deuterium enriched) may be in the range of about 70 mg or higher (free base),25 whereas for deuterated analogs of DMT such as 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,1,2,2-d4(DMT-d10) less drug (e.g., 10 to 50 mg, 15 to 50 mg, 20 to 40 mg, 30 to 50 mg, free base) may be needed to maintain desired blood concentrations owing to its longer half-life in vivo. The lower dosing requirements of deuterated analogs of DMT such as DMT-d10 allow for lower concentrations of release modifier to be used to achieve desirable controlled-release profiles, 30 and for lower injection volumes. Release modifier 136

[0097] The pharmaceutical formulation comprises a release modifier. The release modifier is the component primarily responsible for providing a controlled, tunable, and linear release of the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) upon injection of the pharmaceutical formulation, 5 such as upon subcutaneous injection. Without being limited by theory, it is believed that the release modifier acts by thickening and building viscosity of the pharmaceutical formulation, while potentially also providing electrostatic attraction with the psychopharmaceutical agent, such that upon injection the psychopharmaceutical agent can be slowly released from the injection site (e.g., in the case of subcutaneous injection, within the fat or the layer of skin directly below the dermis 10 and epidermis) and absorbed more slowly, generating a depot-like release effect. The release modifier may be a polymeric material, such as a hyaluronate salt or a carboxymethyl cellulose salt, which may, or may not, be crosslinked. The rate of release of the psychopharmaceutical agent can be controlled through cross-linking or the lack thereof, or the extent of cross-linking of the release modifier. Release modifiers which are not cross-linked will typically provide a shorter release 15 profile than those which are crosslinked, with crosslinking capable of extending the release significantly, such as over the course of a day or multiple days. For delivery of tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)), whereby a controlled-release is sought which provides a duration of peak effects of about 30 to 120 minutes, the release modifier is generally not crosslinked so as not to overextend the release 20 period. For clarity, the release modifier is considered a separate component from the psychopharmaceutical agent. The release modifier is also considered a separate component from the pharmaceutically acceptable additive(s) described hereinafter (such as a buffering agent, a tonicity agent, a pH adjusting agent, etc.) when such pharmaceutically acceptable additives are included in the pharmaceutical formulation of the present disclosure, even though the release 25 modifier may perform a similar function to a particular additive(s). For example, the release modifier is considered different from a tonicity agent even though the release modifier contributes to the overall osmolality of the pharmaceutical formulation. In another example, the release modifier is considered different from a buffering agent or a pH adjusting agent, even though the release modifier may influence the pH of the pharmaceutical formulation. 30 Hyaluronate salt In some embodiments, the release modifier is a hyaluronate salt (anionic salt form of hyaluronic acid), which is non-sulfated glycosaminoglycan and long- 137

[0098] chain polymer of disaccharide units of glucuronate-N-acetylglucosamine. Hyaluronate salts are biocompatible and are distributed widely throughout human connective, epithelial, and neural tissues. The hyaluronate salt may include, but is not limited to, a sodium salt of hyaluronate (sodium hyaluronate), a potassium salt of hyaluronate (potassium hyaluronate), a calcium salt of 5 hyaluronate (calcium hyaluronate), a zinc salt of hyaluronate (zinc hyaluronate), and a magnesium salt of hyaluronate (magnesium hyaluronate), or a combination thereof. In some embodiments, the release modifier is sodium hyaluronate. While not limited thereto, the hyaluronate salt may be produced by a microbial fermentation and purification process and is preferably pharmacopoeia compliant. In terms of purification, hyaluronate salts are known to be heat sensitive, and so cannot 10 be typically sterilized by thermal sterilization methods such as steam sterilization, dry-heat sterilization / depyrogenation, etc., which can cause polymer degradation. Instead, hyaluronate salts are sterilized by sterile filtration such as sterile filtration through a 0.25 μm filter size or less. After sterile filtration, hyaluronate salts may be optionally sterilized with a secondary sterilization process such as ethylene oxide (ETO) gas sterilization or gamma sterilization under less harsh 15 conditions. In some embodiments, the hyaluronate salt is a native hyaluronate salt, meaning it is not substituted, modified with pendant groups, conjugated, crosslinked, or otherwise covalently modified. Rather, the native hyaluronate salt possesses unmodified disaccharide units of glucuronate-N-acetylglucosamine. Examples may include, but are not limited to, sodium 20 hyaluronate products available from Lifecore Biomedical, Inc. In some embodiments, the hyaluronate salt is a non-native hyaluronate salt, i.e., those that are substituted, modified with pendant groups, conjugated, crosslinked, deacetylated, or otherwise covalently modified. The non-native hyaluronate salts may be, inter alia, acetylated, deacetylated, alkylated, esterified, amidated, hydrazidated, epoxy grafted, silylated, sulfated, and / or crosslinked 25 hyaluronate salts. These modifications such as crosslinking may enable the formation of hydrogels of hyaluronate salts. The degree of modification or substitution in non-native hyaluronate salts is typically about 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, or any range therebetween. Examples of non-native hyaluronate salts include, but are not limited to, sodium hyaluronate salts modified with pendant tyramine groups (an amidated hyaluronate salt) whereby 30 tyramine is introduced onto glucuronate units using amide bond chemistry (EDC chemistry); and Corgel® BioHydrogel products available from Lifecore Biomedical, Inc., whereby the tyramine substituted sodium hyaluronate (TS-NaHy) from above is subsequently cross-linked by forming 138

[0099] stable dihydroxyphenyl covalent bonds through an enzyme driven reaction involving e.g., horseradish peroxidase. While crosslinked or hydrogels of hyaluronate salts may be employed in some cases, for the delivery of tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) in which a controlled-release is sought that provides 5 a duration of peak effects of about 30 to 120 minutes, the hyaluronate salt is generally not crosslinked or in hydrogel form so as not to overextend the release period and the resulting duration of peak effects beyond about 120 minutes. The weight average molecular weight (Mw) of the hyaluronate salt may be about 500 kDa, about 550 kDa, about 600 kDa, about 650 kDa, about 700 kDa, about 750 kDa, about 800 kDa, 10 about 850 kDa, about 900 kDa, about 950 kDa, about 1,000 kDa, about 1,200 kDa, about 1,300 kDa, about 1,400 kDa, about 1,500 kDa, about 1,600 kDa, about 1,700 kDa, about 1,800 kDa, about 1,900 kDa, about 2,000 kDa, or any range therebetween such as from about 500 kDa to about 2,000 kDa, from about 600 kDa to about 1,500 kDa, from about 750 kDa to about 1,000 kDa, from about 1,000 kDa to about 2,000 kDa, from about 1,000 kDa to about 1,900 kDa, from 15 about 1,000 kDa to about 1,800 kDa, from about 1,200 kDa to about 1,800 kDa, from about 1,500 kDa to about 1,700 kDa, from about 1,600 kDa to about 1,800 kDa. A weight average molecular weight of the hyaluronate salt which is above the aforementioned upper limit may result in pharmaceutical formulations which are too viscous, thereby complicating the sterile filtration process and resulting in painful injections, especially in the case of subcutaneous injections. 20 Further, hyaluronate salts with a weight average molecular weight above the aforementioned upper limit may provide a release profile which is too slow for achieving the desired peak effects time course of about 30 to 120 minutes in the case of some tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)). On the other hand, hyaluronate salts with a weight average molecular weight below the aforementioned lower limit 25 may not provide any meaningful controlled-release effects, and the pharmaceutical formulation may instead behave similarly to those which are formulated without any release modifier. In some embodiments, the hyaluronate salt has a molecular weight range in between about 500 kDa, about 600 kDa, about 700 kDa, about 800 kDa, about 900 kDa, about 1,000 kDa, about 1,100 kDa, about 1,200 kDa, about 1,300 kDa, about 1,400 kDa, about 1,500 kDa, about 1,600 kDa, about 1,700 30 kDa, about 1,800 kDa, about 1,900 kDa, and about 2,000 kDa, or any intermediate range between any of these values. In some embodiments, the hyaluronate salt has a molecular weight range of about 500 kDa to about 2,000 kDa. In some embodiments, the hyaluronate salt has a molecular 139

[0100] weight range of about 500 kDa to about 750 kDa. In some embodiments, the hyaluronate salt has a molecular weight range of about 750 kDa to about 1,000 kDa. In some embodiments, the hyaluronate salt has a molecular weight range of about 750 kDa to about 1,500 kDa. In some embodiments, the hyaluronate salt has a molecular weight range of about 1,000 kDa to about 1,800 5 kDa. In some embodiments, the hyaluronate salt has a molecular weight range of about 900 kDa to about 1,400 kDa. The weight average molecular weight of the hyaluronate salt would then fall somewhere within the molecular weight range. Examples of suitable hyaluronate salts include, but are not limited to, sodium hyaluronate products HA700K (molecular weight range of 500 – <750 kDa), HA1M (molecular weight range 10 of 750 – 1,000 kDa), and HA15M (molecular weight range of >1,000 – 1,800 kDa), available from Lifecore Biomedical, Inc., and Hyatrue® HA-EP1.8 (molecular weight range of 900-1,400 kDa) available from Bloomage Freda Biopharm Co. Ltd. A concentration of hyaluronate salt by weight per total volume of the pharmaceutical formulation expressed as a percentage (% w / v) may be about 0.02%, about 0.03%, about 0.04%, 15 about 0.05%, about 0.06%, about 0.08%, about 0.09%, about 0.1%, about 0.15%, about 0.2%, about 0.25%, about 0.3%, about 0.35%, about 0.4%, about 0.45%, about 0.5%, about 0.55%, about 0.6%, about 0.65%, about 0.7%, about 0.75%, about 0.8%, about 0.85%, about 0.9%, about 0.95%, about 1%, about 1.1%, about 1.2%, about 1.3%, about 1.4%, about 1.5%, about 1.6%, about 1.7%, about 1.8%, about 1.9%, about 2%, or any range therebetween, such as from about 0.1% to about 20 2%, about 0.1% to about 1.5%, about 0.1% to about 1%, about 0.1% to about 0.75%, about 0.1% to about 0.5%, about 0.15% to about 1%, about 0.2% to about 0.75%, or about 0.25% to about 0.5%. As the concentration of hyaluronate salt is increased, so to is the viscosity of the pharmaceutical formulation. Exceeding viscosity specifications is problematic for sterile filtration (and hyaluronate salts are sensitive to thermal sterilization techniques) and may cause increased 25 pain at the injection site. Moreover, in the case of tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) in which a release is sought that provides a peak effects time course of about 30 to 120 minutes, too high a concentration of hyaluronate salt may overextend the release profile and the resulting duration of peak effects beyond about 120 minutes, which is not clinically favorable as it would necessitate prolonged 30 supervised clinical observation. For these reasons, in such embodiments, the concentration of hyaluronate salt preferably does not exceed about 1%, about 0.95%, about 0.9%, about 0.85%, about 0.8%, about 0.75%, about 0.7%, about 0.65%, about 0.6%, about 0.55%, about 0.5% w / v. 140

[0101] In preferred embodiments, the concentration of hyaluronate salt is from about 0.1% to about 0.5% w / v. Attempts to lower the concentration of hyaluronate salt by dilution (increasing injection volume) may not be possible in subcutaneous dosage forms, for example, since higher injection volumes, especially those above 3 mL, are associated with pain at the injection site. Conversely, 5 hyaluronate salt concentrations which are below the aforementioned lower limit may not provide any meaningful controlled-release effects, and the pharmaceutical formulation may instead behave similarly to those which are formulated without any release modifier. In some embodiments, a ratio of free base concentration of psychopharmaceutical agent, (e.g., a free base concentration of a compound of Formula (I) through (III)), in terms of weight per 10 total volume of pharmaceutical formulation (mg / mL), to the concentration of hyaluronate salt by weight per total volume of the pharmaceutical formulation expressed as a percentage (% w / v) is about 10:1, about 15:1, about 20:1, about 25:1, about 30:1, about 35:1, about 40:1, about 45:1, about 50:1, about 55:1, about 60:1, about 65:1, about 70:1, about 75:1, about 80:1, about 85:1, about 90:1, about 95:1, about 100:1, about 105:1, about 110:1, about 115:1, about 120:1, about 15 125:1, about 130:1, or any range therebetween, such as from about 10:1 to about 130:1, about 15:1 to about 120:1, about 20:1 to about 110:1, or about 25:1 to about 100:1. In the case of tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) in which a release profile is sought that provides a peak effects duration of about 30 to 120 minutes, ratios below the aforementioned lower limit may result in pharmaceutical formulations with a 20 release profile which is overextended (too slow) in terms of clinical practicality. Ratios above the aforementioned upper limit tend to provide a release that is not meaningfully different from formulations lacking release modifier (too fast). Even so, there are instances where higher ratios of free base concentration of psychopharmaceutical agent (mg / mL) to the concentration of hyaluronate salt (% w / v) can be used, for example up to about 500:1, about 400:1, about 300:1, 25 about 200:1, or about 140:1, such as when a faster release profile is desirable or where other parameters in the formulation can counteract any fast release effects attributable to the use of such higher ratios. In some embodiments, a ratio of the weight average molecular weight (Mw) of the hyaluronate salt (in kDa) to a free base concentration of psychopharmaceutical agent, (e.g., a free 30 base concentration of a compound of Formula (I) through (III)), in terms of weight per total volume of pharmaceutical formulation (mg / mL), is about 17:1, about 18:1, about 19:1, about 20:1, about 25:1, about 30:1, about 35:1, about 40:1, about 45:1, about 50:1, about 55:1, about 60:1, about 141

[0102] 65:1, about 70:1, about 75:1, about 80:1, about 85:1, about 90:1, about 95:1, about 100:1, or any range therebetween, such as from about 17:1 to about 100:1, about 20:1 to about 100:1, about 22:1 to about 80:1, about 24:1 to about 60:1, or about 25:1 to about 55:1, or about 26:1 to about 100:1, or about 28:1 to about 100:1, or about 30:1 to about 75:1. Ratios below the aforementioned lower 5 limit may result in pharmaceutical formulations with a release profile similar to those which are formulated without any release modifier (too fast), whereas ratios above the aforementioned upper limit may overextend the release (too slow) and the resulting duration of peak effects, which is not favorable in the case of certain tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)). In some embodiments, such as when the 10 psychopharmaceutical agent is a pharmaceutically acceptable salt of a compound of Formula (III), a ratio of the weight average molecular weight of the hyaluronate salt (in kDa) to a free base concentration of psychopharmaceutical agent, in terms of weight per total volume of pharmaceutical formulation (mg / mL), is preferably about 30:1, about 31:1, about 32:1, about 33:1, about 34:1, about 35:1, about 40:1, about 45:1, about 50:1, about 55:1, about 60:1, about 15 65:1, about 70:1, about 75:1, about 80:1, about 85:1, about 90:1, about 95:1, about 100:1, or any range therebetween, such as from about 35:1 to about 100:1, about 40:1 to about 100:1, about 42:1 to about 80:1, about 44:1 to about 60:1, or about 45:1 to about 55:1. Carboxymethyl cellulose salt In some embodiments, the release modifier is a carboxymethyl cellulose salt, which is a 20 cellulose derivative with carboxymethyl groups (-CH2COO-) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. The carboxymethyl cellulose salt may include, but is not limited to, a sodium salt of carboxymethyl cellulose (sodium carboxymethyl cellulose). While not limited thereto, the carboxymethyl cellulose salt may be produced by reacting alkali cellulose with sodium monochloroacetate, and this reaction may be 25 performed under rigidly controlled conditions to control the degree of substitution (DS), which is the average number of hydroxyl groups of the glucopyranose monomers that are carboxymethylated, with the theoretical limit being a DS of 3.0. The resultant polymer is purified and dried for pharmacopoeia compliance. In some embodiments, the carboxymethyl cellulose salt is not substituted, modified with 30 pendant groups, conjugated, crosslinked, or otherwise covalently modified. Rather, the carboxymethyl cellulose salt possesses a cellulose backbone formed from glucopyranose monomers which are substituted only with carboxymethyl groups. For example, in some 142

[0103] embodiments, the carboxymethyl cellulose salt is not crosslinked with glycolic acid to form a croscarmellose salt such as sodium croscarmellose. The carboxymethyl cellulose salt may have a degree of substitution (DS) of 0.7, 0.75, 0.8, 0.85, 0.9, 0.95, 1.0, 1.05, 1.1, 1.15, 1.2, or any range therebetween, such as from 0.45 to less than 5 0.9, from 0.9 to less than 1.2, or from 1.2 to 1.5. In some embodiments, the carboxymethyl cellulose salt has a DS of 0.85 to 1.15 or 0.9 to 1.0. The weight average molecular weight (Mw) of the carboxymethyl cellulose salt is typically below about 500 kDa, for example, about 50 kDa, about 60 kDa, about 70 kDa, about 80 kDa, about 90 kDa, about 100 kDa, about 110 kDa, about 120 kDa, about 130 kDa, about 140 kDa, 10 about 150 kDa, about 160 kDa, about 170 kDa, about 180 kDa, about 190 kDa, about 200 kDa, about 210 kDa, about 220 kDa, about 230 kDa, about 240 kDa, about 250 kDa, about 300 kDa, about 350 kDa, about 400 kDa, about 450 kDa, or any range therebetween, such as from about 90 kDa to about 300 kDa, from about 100 kDa to about 300 kDa, from about 100 kDa to about 275 kDa, from about 150 kDa to about 250 kDa. A weight average molecular weight of the 15 carboxymethyl cellulose salt which is above the aforementioned upper limit generally results in pharmaceutical formulations that exceed viscosity specifications for being injectable and syringeable, and are not generally approved by the Food & Drug Administration (FDA) for use in injectables. Accordingly, suitable carboxymethyl cellulose salts are typically those with a Brookfield viscosity, measured as 2% aqueous solutions using spindle number 3 at 30 rpm, of 20 from about 400 cP, about 600 cP, about 800 cP, about 1,000 cP, about 1,200 cP, about 1,500 cP, about 1,750 cP, about 2,000 cP, about 2,250 cP, about 2,500 cP, about 2,750 cP, about 3,000 cP, about 3,100 cP, or any range therebetween, such as from about 400 cP to about 3,100 cP or about 1,500 cP to about 3,100 cP. Examples of the carboxymethyl cellulose salt may include, but are not limited to, 25 Aqualon™ and Blanose™ sodium carboxymethyl cellulose products available from Ashland, such as Aqualon™ / Blanose™ grades 9M8F PH, 9M8XF, 9M31F PH, 9M31XF PH, and 7MF PH. In some embodiments, the carboxymethyl cellulose salt is 7MF PH from Ashland (sodium carboxymethyl cellulose; Mw = 250 kDa; DS = 0.7; Brookfield viscosity, measured as 2% aqueous solution using spindle number 3 at 30 rpm, of from 400 cP to 800 cP). 30 A concentration of carboxymethyl cellulose salt by weight per total volume of the pharmaceutical formulation expressed as a percentage (% w / v) may be about 0.55%, about 0.6%, about 0.65%, about 0.7%, about 0.75%, about 0.8%, about 0.85%, about 0.9%, about 0.95%, about 143

[0104] 1%, or any range therebetween, such as from about 0.6% to about 1%, about 0.7% to about 1%, about 0.75% to about 1%, about 0.75% to about 0.9%, about 0.75% to about 0.8%. Concentrations of carboxymethyl cellulose salt which exceed the aforementioned upper limit provide pharmaceutical formulations which are too viscous for sterile filtration, injectability, and / or 5 syringeability, for example may cause increased pain at the injection site. On the contrary, carboxymethyl cellulose salt concentrations which are below the aforementioned lower limit may not provide any meaningful controlled-release effects, and the pharmaceutical formulation may instead behave similarly to those which are formulated without any release modifier. In some embodiments, a ratio of free base concentration of psychopharmaceutical agent, 10 (e.g., a free base concentration of a compound of Formula (I) through (III)), in terms of weight per total volume of pharmaceutical formulation (mg / mL), to the concentration of carboxymethyl cellulose salt by weight per total volume of the pharmaceutical formulation expressed as a percentage (% w / v) is about 10:1, about 15:1, about 20:1, about 25:1, about 30:1, about 35:1, about 40:1, about 45:1, about 50:1, about 55:1, about 60:1, about 65:1, about 70:1, about 75:1, about 15 80:1, about 85:1, about 90:1, about 95:1, about 100:1, or any range therebetween, such as from about 10:1 to about 100:1, about 13:1 to about 90:1, about 15:1 to about 75:1, or about 20:1 to about 50:1. In some embodiments, a ratio of the weight average molecular weight of the carboxymethyl cellulose salt (in kDa) to a free base concentration of psychopharmaceutical agent, (e.g., a free 20 base concentration of a compound of Formula (I) through (III)), in terms of weight per total volume of pharmaceutical formulation (mg / mL), is about 1:1, about 2:1, about 3:1, about 4:1, about 5:1, about 6:1, about 8:1, about 10:1, about 12:1, about 14:1, about 16:1, about 18:1, about 20:1, about 22:1, about 24:1, about 26:1, about 28:1, about 30:1, about 32:1, about 34:1, about 36:1, about 38:1, about 40:1, about 42:1, about 44:1, about 46:1, about 48:1, about 50:1, or any range 25 therebetween, such as from about 1:1 to about 50:1, about 5:1 to about 40:1, about 10:1 to about 30:1, about 15:1 to about 20:1, or about 1:1 to about 10:1. Aqueous vehicle The pharmaceutical formulation comprises an aqueous vehicle. The term “vehicle” herein 30 refers to a diluent, adjuvant, excipient, carrier, and / or any other auxiliary or supporting ingredient with which a psychopharmaceutical agent and release agent of present disclosure is formulated for administration to a mammal. The aqueous vehicle, and thus the pharmaceutical formulation, 144

[0105] comprises water, such as water for injection (WFI). Suitable aqueous vehicles include, but are not limited to, water, saline, physiological or isotonic saline, phosphate buffered saline (PBS), sodium chloride injection, Ringers injection, isotonic dextrose injection, sterile water injection, dextrose and lactated Ringers injection. 5 In addition to water, the aqueous vehicle, and thus the pharmaceutical formulation, may optionally contain one or more pharmaceutically acceptable additives, as desired / needed. “Pharmaceutically acceptable additives” may be diluents, adjuvants, excipients, carriers, or any other auxiliary or supporting ingredient approved by a regulatory agency of the Federal or a state government or listed in the U.S. Pharmacopeia or other generally recognized pharmacopeia for 10 use in mammals, such as humans. Examples of pharmaceutically acceptable additives include, but are not limited to, water-miscible vehicles, non-aqueous vehicles, antimicrobial agents or preservatives against the growth of microorganisms, stabilizing agents, tonicity agents, buffering agents, antioxidants, local anesthetics, complexing agents, sequestering or chelating agents, pH adjusting agents, absorption enhancers, including combinations thereof. It should be understood 15 that many pharmaceutically acceptable additives may serve several functions, even within the same pharmaceutical formulation, for example, a buffering agent may also act as a tonicity agent and vice versa. Water-miscible vehicles include, but are not limited to, ethanol, 1,3-butanediol, liquid polyethylene glycol (e.g., polyethylene glycol 300 and polyethylene glycol 400), propylene glycol, 20 glycerin, N-methyl-2-pyrrolidone, dimethylacetamide, and dimethylsulfoxide, or a combination thereof. Non-aqueous vehicles include, but are not limited to, fixed oils of vegetable origin, castor oil, corn oil, cottonseed oil, olive oil, peanut oil, peppermint oil, safflower oil, sesame oil, soybean oil, hydrogenated vegetable oils, hydrogenated soybean oil, and medium-chain 25 triglycerides of coconut oil, and palm seed oil, or a combination thereof. Antimicrobial agents or preservatives include, but are not limited to, phenols (e.g., phenol), cresols, mercurials, benzyl alcohol, chlorobutanol, methyl and propyl p-hydroxybenzates, thimerosal, benzalkonium chloride, benzethonium chloride, methyl-, ethyl-, and propyl-parabens, benzoic acid, sodium benzoate, and sorbic acid, or a combination thereof. 30 Stabilizing agents include, but are not limited to, fatty acids, fatty alcohols, alcohols, long chain fatty acid esters, long chain ethers, hydrophilic derivatives of fatty acids, polyvinyl pyrrolidones, polyvinyl ethers, polyvinyl alcohols, glycerol, methionine, monothioglycerol, 145

[0106] ascorbic acid, citric acid, polysorbate, arginine, and sorbitol, or a combination thereof. For example, fatty acids may act as lipid carriers. The fatty acid may have from 4 to 30 carbon atoms, 6 to 28 carbon atoms, 8 to 24 carbon atoms, 10 to 20 carbon atoms, or 12 to 18 carbon atoms. The fatty acid may be a fatty monoacid or a fatty diacid. Exemplary fatty acids may include, but are 5 not limited to, adipic (hexandioic) acid, lauric (dodecanoic) acid, linoleic acid, myristic (tetradecanoic) acid, capric (decanoic) acid, stearic (octadecanoic) acid, oleic acid, caprylic (octanoic) acid, palmitic (hexadecenoic) acid, sebacic acid, undecylenic acid, caproic acid, arachidic acid, behenic acid, lignoceric acid, palmitolic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid, docosahexaenoic acid, and combinations thereof. In some embodiments, 10 the pharmaceutical formulation is formulated without a fatty acid to prevent hydrogel formation and an overextended release (for an example of a hydrogel that generates a release over days, see Kang NW, et al. Subcutaneously Injectable Hyaluronic Acid Hydrogel for Sustained Release of Donepezil with Reduced Initial Burst Release: Effect of Hybridization of Microstructured Lipid Carriers and Albumin. Pharmaceutics.2021 Jun 11;13(6):864). 15 A tonicity agent is a chemical that, on inclusion within a pharmaceutical formulation, modulates the osmolality of the pharmaceutical formulation. Sometimes, the concentration of psychopharmaceutical agent and the release modifier in the pharmaceutical formulation provides a desired osmolality, and so no tonicity agent is needed / included. Alternatively, the concentration of psychopharmaceutical agent and the release modifier in the pharmaceutical formulation does 20 not provide the osmolality specifications for injection, and so one or more tonicity agents may be included to reach a desired osmolality. When the pharmaceutical formulation comprises a tonicity agent, the concentration of the tonicity agent will be adjusted considering the osmolality contributions from the concentrations of psychopharmaceutical agent and the release modifier to provide a pharmaceutical formulation with a desirable osmolality range (e.g., 150 to 600 25 mOsm / kg). Tonicity agents include, but are not limited to, sodium chloride; potassium chloride; calcium chloride; magnesium chloride; dextrose; glucose; mannitol; lactose; sorbitol; sucrose; alanine; ethanol; benzyl alcohol; creatinine; glycine; glycerol; histidine; polyethylene glycol; propylene glycol; sodium bicarbonate; sodium hydroxide; hydrochloric acid; phosphoric acid; a phosphate salt such as sodium phosphate or potassium phosphate; acetic acid; an acetate salt such 30 as sodium acetate, potassium acetate, or ammonium acetate; citric acid; a citrate salt such as sodium citrate or potassium citrate; arginine; ascorbic acid; an ascorbate salt such as potassium ascorbate or sodium ascorbate; edetic acid; an edetate salt such as sodium edetate or calcium 146

[0107] edetate; lactic acid; a lactate salt such as potassium lactate or sodium lactate; tartaric acid; a tartrate salt such as sodium tartrate or potassium tartrate, as well as combinations thereof. In some embodiments, the tonicity agent is at least one selected from the group consisting of sodium chloride, potassium chloride, calcium chloride, sodium bicarbonate, magnesium chloride, 5 dextrose, glucose, mannitol, lactose, sorbitol, sucrose, and sodium lactate. Typically, the tonicity agent is sodium chloride. In some embodiments, the pharmaceutical formulation comprises sodium chloride at a concentration, in terms of weight per total volume of the pharmaceutical formulation expressed as a percentage (% w / v), of about 0.1%, about 0.2%, about 0.3%, about 0.4%, about 0.5%, about 0.6%, about 0.7%, about 0.8%, or any range therebetween such as from 10 about 0.1% to about 0.6%, about 0.2% to about 0.55%, about 0.3% to about 0.5% w / v. A buffering agent is a chemical that on inclusion into the pharmaceutical formulation comprises a weak acid and its conjugate base in equilibrium, which resist changes in pH on addition of acid or base to the pharmaceutical formulation. In other words, addition of acid or base to the pharmaceutical formulation shifts the position of equilibrium in favor of the weak acid or 15 conjugate base, respectively, and as a consequence, the concentration of free protons in the pharmaceutical formulation (and thus the pH) is relatively unchanged or changed by less than the amount expected for the quantity of acid or base added (until the buffer capacity is reached). For clarity, the buffering agent is considered a separate component from the psychopharmaceutical agent (e.g., a pharmaceutically acceptable salt of a compound of the present disclosure such as a 20 pharmaceutically acceptable salt of a compound of Formula (I) through (III)). In this sense, the buffering agent is not merely a counterion to the protonated form of the compound of the present disclosure. Rather the buffering agent, when included, provides a buffering effect to resist changes in pH above that which may be provided by the psychopharmaceutical agent. The buffering agent is also considered a separate component from the release modifier, and again, provides a buffering 25 effect to resist changes in pH above that which may be provided by the release modifier. Buffering agents include, but are not limited to, a phosphate buffer (a phosphate salt and phosphoric acid; pKa = 2.14, 7.20, and 12.37), an acetate buffer (an acetate salt and acetic acid; pKa = 4.76), a citrate buffer (a citrate salt and citric acid; pKa = 3.13, 4.76, and 6.40), an ascorbate buffer (an ascorbate salt and ascorbic acid; pKa = 4.10 and 11.6), a benzoate buffer (a benzoate salt and 30 benzoic acid; pKa = 4.20), an oxalate buffer (an oxalate salt and oxalic acid; pKa = 1.25 and 4.14), a formate buffer (a formate salt and formic acid; pKa = 3.75), or a combination thereof. Generally, a suitable buffer is optionally selected that comprises an acid with a pKa value (or an acid having 147

[0108] at least one pKa value in the case of polyprotic acids) that lies within ±1 of the desired pH of the pharmaceutical formulation. In some embodiments, the pharmaceutical formulation is not formulated with a buffering agent. Antioxidants include, but are not limited to, bisulfite and sodium metabisulfite, ascorbic 5 acid, citric acid, tartaric acid, thiol derivatives, or combinations thereof. In some embodiments, the pharmaceutical formulation has an oxygen content of less than 2 ppm, such as between 0.1 ppm and 2 ppm. Local anesthetics include, but are not limited to, procaine hydrochloride. Complexing agents include, but are not limited to, cyclodextrins, including ca- 10 cyclodextrin, β-cyclodextrin, hydroxypropyl-3-cyclodextrin, sulfobutylether-β-cyclodextrin, and sulfobutylether 7-O-cyclodextrin (CAPTISOL®, CyDex, Lenexa, Kans.), or combinations thereof. Sequestering or chelating agents include, but are not limited to EDTA. pH adjusting agents include, but are not limited to, sodium hydroxide, potassium 15 hydroxide, sodium carbonate, ammonium hydroxide, calcium hydroxide, magnesium hydroxide, hydrochloric acid, citric acid, and lactic acid, or combinations thereof. Absorption enhancers include, but are not limited to, a hyaluronidase enzyme. In pharmaceutical formulations containing a hyaluronate salt, the hyaluronidase enzyme may have the added effect of breaking down the hyaluronate salt to speed drug release in cases where 20 increased release rates are desired. This additive may be added to the pharmaceutical formulation immediately prior to injection or may be injected separately as part of a multi-component injection, such as using a dual chamber syringe or a multi-syringe (e.g., two syringe) set up. In some embodiments, the pharmaceutical formulation does not contain a hyaluronidase enzyme, nor is a hyaluronidase enzyme employed during or post injection of the pharmaceutical formulation. 25 In some embodiments, the pharmaceutical formulation comprises the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)); the release modifier; and an aqueous vehicle made up of saline, optionally a buffering agent, optionally a pH adjusting agent (e.g., sodium hydroxide), and optionally a tonicity agent other than sodium chloride. In some embodiments, the 30 pharmaceutical formulation comprises the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)); the release modifier; and an aqueous vehicle made up of water for injection, optionally a 148

[0109] buffering agent, optionally a pH adjusting agent (e.g., sodium hydroxide), and optionally a tonicity agent. In some embodiments, the pharmaceutical formulation comprises the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)); the release modifier; and an aqueous vehicle made up of water for 5 injection, optionally a buffering agent, optionally a pH adjusting agent (e.g., sodium hydroxide), wherein the aqueous vehicle does not contain a tonicity agent such as sodium chloride. In some embodiments, the pharmaceutical formulation comprises the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)); the release modifier; and an aqueous vehicle made up of water for injection or 10 saline, and optionally a pH adjusting agent (e.g., sodium hydroxide), wherein the pharmaceutical formulation is formulated without a buffering agent. In some embodiments, the pharmaceutical formulation consists of, or consists essentially of, the psychopharmaceutical agent (e.g., a tryptamine psychedelic such as a pharmaceutically acceptable salt of a compound of Formula (I) through (III)); the release modifier; and water and optional tonicity agent (e.g., sodium chloride) 15 as the aqueous vehicle. By consists essentially of, it is meant that the presence of additional components within the pharmaceutical formulation is permitted, provided the amounts of such additional components do not materially affect the essential characteristics of the pharmaceutical formulation—namely that the pharmaceutical formulation is suitable for injection and provides time-restricted temporal controlled-release of a psychopharmaceutical agent. In some 20 embodiments of administering tryptamine psychedelics (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)), this time-restricted controlled-release would provide a duration of peak effects of about 30 to 120 minutes. Physiochemical properties 25 The pharmaceutical formulation may have a pH of about 2, about 2.25, about 2.5, about 2.75, about 3, about 3.25, about 3.5, about 3.75, about 4, about 4.25, about 4.5, about 4.75, about 5, about 5.25, about 5.5, about 5.75, about 6, about 6.25, about 6.5, about 6.75, about 7, about 7.25, about 7.5, about 7.75, about 8, about 8.25, about 8.5, about 8.75, about 9, about 9.25, about 9.5, about 9.75, about 10, about 10.25, about 10.5, about 10.75, about 11, or any range 30 therebetween. Generally, pH values which are too high are associated with tissue necrosis, whereas pH values which are too low are associated with pain and inflammation at the injection site. In some embodiments, the pharmaceutical formulation is suitable for intravenous injection (is an 149

[0110] intravenous pharmaceutical formulation) or intramuscular injection (is an intramuscular pharmaceutical formulation), and has a pH ranging from about 2 to about 11, about 3 to about 9, about 4 to about 7, about 4.5 to about 6. In some embodiments, the pharmaceutical formulation is suitable for subcutaneous injection (is a subcutaneous pharmaceutical formulation), and has a pH 5 ranging from about 3 to about 9, about 3 to about 7, about 4 to about 9, about 4 to about 7.5, about 4 to about 7, about 4.5 to about 7.5, about 4.5 to about 7, about 4.5 to about 6.5, about 4.5 to about 6. The pharmaceutical formulation may have an osmolality of about 150 mOsm / kg, about 155 mOsm / kg, about 160 mOsm / kg, about 165 mOsm / kg, about 170 mOsm / kg, about 175 10 mOsm / kg, about 180 mOsm / kg, about 185 mOsm / kg, about 190 mOsm / kg, about 195 mOsm / kg, about 200 mOsm / kg, about 225 mOsm / kg, about 250 mOsm / kg, about 275 mOsm / kg, about 300 mOsm / kg, about 325 mOsm / kg, about 350 mOsm / kg, about 375 mOsm / kg, about 400 mOsm / kg, about 425 mOsm / kg, about 450 mOsm / kg, about 475 mOsm / kg, about 500 mOsm / kg, about 525 mOsm / kg, about 550 mOsm / kg, about 575 mOsm / kg, about 600 mOsm / kg, or any range 15 therebetween, such as from about 150 to about 600 mOsm / kg, about 200 to about 500 mOsm / kg, about 250 to about 550 mOsm / kg, about 275 to about 500 mOsm / kg, about 300 to about 450 mOsm / kg, about 150 mOsm / kg to about 200 mOsm / kg, about 150 mOsm / kg to about 175 mOsm / kg. Osmolalities which are outside of these values are reported to cause pain. In some embodiments, the pharmaceutical formulation is isotonic with human blood serum, i.e., has an 20 osmolality of about 275 to about 300 mOsm / kg. The pharmaceutical formulation may have viscosity of less than about 10,000 cP, less than about 9,000 cP, less than about 8,000 cP, less than about 7,000 cP, less than about 6,000 cP, less than about 5,000 cP, less than about 4,000 cP, less than about 3,000 cP, less than about 2,000 cP, less than about 1,000 cP, less than about 500 cP, less than about 100 cP, less than about 50 cP, less 25 than about 45 cP, less than about 40 cP, less than about 35 cP, less than about 30 cP, less than about 25 cP, less than about 20 cP, for example, about 1 cP, about 2 cP, about 3 cP, about 4 cP, about 5 cP, about 8 cP, about 10 cP, about 12 cP, about 15 cP, about 18 cP, about 20 cP, about 22 cP, about 25 cP, about 28 cP, about 30 cP, about 32 cP, about 35 cP, about 38 cP, about 40 cP, about 42 cP, about 45 cP, about 50 cP, about 60 cP, about 70 cP, about 80 cP, about 90 cP, about 30 100 cP, about 150 cP, about 200 cP, about 250 cP, about 300 cP, about 350 cP, about 400 cP, about 500 cP, about 600 cP, about 800 cP, about 1,000 cP, about 1,200 cP, about 1,500 cP, about 1,750 cP, about 2,000 cP, about 2,250 cP, about 2,500 cP, about 2,750 cP, about 3,000 cP, about 3,100 150

[0111] cP, about 3,500 cP, about 4,000 cP, about 4,500 cP, about 5,000 cP, about 6,000 cP, about 7,000 cP, about 8,000 cP, about 9,000 cP, about 10,000 cP, or any range therebetween. Such viscosity values allow the pharmaceutical formulation to be syringeable and injectable, for example without causing excessive pain at the injection site. In some embodiments, such as when the release 5 modifier employed is a hyaluronate salt, suitable viscosity values also enable the use of sterile filtration as the sterilization technique. In some embodiments, the pharmaceutical formulation is suitable for subcutaneous injection (is a subcutaneous pharmaceutical formulation), and preferably has a viscosity of less than about 3,000 cP, less than about 2,500 cP, less than about 2,000 cP, less than about 1,500 cP, less than about 1,000 cP, less than about 500 cP, less than about 100 cP, less 10 than about 50 cP, less than about 25 cP, less than about 20 cP, for example, about 1 cP, about 2 cP, about 3 cP, about 4 cP, about 5 cP, about 8 cP, about 10 cP, about 12 cP, about 15 cP, about 18 cP, about 20 cP, about 22 cP, or any range therebetween. In some embodiments, the pharmaceutical formulation has a shelf-life as an aqueous solution of at least 1 day, 2 days, 3 days, 4 days 5 days, 6 days, 1 week, 2 weeks, 3 weeks, 4 weeks, 15 5 weeks, 6 weeks, or longer, without significant product degradation or physical changes such as precipitation. In some embodiments, the pharmaceutical formulation can be maintained / stored as an aqueous solution in open or closed environments, such as in open or closed flasks / vials under sub-ambient, ambient, or stress conditions (elevated temperatures) without appreciable degradation or physical changes such as precipitation. Pharmaceutical formulations with a 20 prolonged shelf-life of at least several days or at least several weeks are advantageous because they may be prepared well in advance of administration if desired, and optionally stored, without materially affecting efficacy or injectability. In some embodiments, pharmaceutical formulations formed from a pharmaceutically acceptable salt of a compound of the present disclosure, e.g., a compound of Formula (I) through (III), as the psychopharmaceutical agent, are characterized by 25 increased stability compared to formulations prepared using the same compound as free base but are otherwise substantially the same. For example, the pharmaceutical formulation of the present disclosure formed from a pharmaceutically acceptable salt of a compound of the present disclosure, e.g., a compound of Formula (I) through (III), may be at least 5%, at least 10%, at least 15%, at least 20%, at least 25%, at least 30%, at least 35%, at least 40%, at least 45%, at least 30 50%, at least 55%, at least 60%, at least 65%, at least 70% more stable upon storage for 24 hours, 48 hours, 72 hours, 1 week, 2 weeks, 3 weeks, 4 weeks, or longer, in terms of degradation or physical changes such as precipitation, compared to formulations prepared from a free base 151

[0112] counterpart but are otherwise substantially the same. Release kinetics The pharmaceutical formulation enables time-restricted temporal controlled-release of the 5 psychopharmaceutical agent via bolus injection to humans, and via bolus subcutaneous injection in particular. In the case of delivering a tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)), the pharmaceutical formulations enable controlled-release of the tryptamine psychedelic via bolus injection to humans, and via bolus subcutaneous injection in particular, that mimics the clinically advantageous peak effects 10 time course of about 30 to 120 minutes achievable by IV infusion of such psychopharmaceutical agents over about 90 minutes. In some embodiments, the duration of peak effects following bolus injection of the pharmaceutical formulation, preferably bolus subcutaneous injection of the pharmaceutical formulation, is about 30 minutes, about 35 minutes, about 40 minutes, about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 15 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 minutes, about 100 minutes, about 105 minutes, about 110 minutes, about 115 minutes, about 120 minutes, or any range therebetween, such as from about 30 to about 120 minutes, from about 30 to about 45 minutes, from about 40 to about 100 minutes, from about 45 to about 90 minutes, from about 50 to about 75 minutes, from about 60 to about 70 minutes. 20 In some embodiments, the controlled-release of a psychedelic (e.g., tryptamine psychedelic) places the patient into a psychedelic state (a correlate of positive clinical outcomes) for about 35 minutes, about 40 minutes, about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 minutes, about 100 minutes, about 105 minutes, about 110 25 minutes, about 115 minutes, about 120 minutes, about 130 minutes, about 140 minutes, about 150 minutes, about 160 minutes, about 170 minutes, about 180 minutes, or any range therebetween, such as a psychedelic state time course of from about 35 minutes to about 100 minutes, from about 40 minutes to about 80 minutes, from about 35 to about 45 minutes, from about 50 minutes to about 60 minutes, from about 40 minutes to about 50 minutes, from about 90 minutes to about 120 30 minutes. Non-limiting examples of PD clinical scales, diary assessments, and assessments by a clinician or caregiver which can be used to assess the duration of action, duration of psychedelic 152

[0113] state, duration of peak effects, mental state, mood, drug effect, etc. of the patient following injection include, but are not limited to, Mystical Experience Questionnaire (MEQ30), the 5- Dimensional Altered States of Consciousness Rating Scale (5D-ASC), the Hallucinogen Rating Scale (HRS), the visual analogue scale (VAS) ratings of ‘Any drug effect’, a 5-item Persisting 5 Effects Questionnaire (PEQ) assessing the meaningfulness, spirituality and psychological insights and challenges of the experience and overall drug effect, the NeuroCart test battery (e.g., saccadic eye movements, smooth pursuit eye movements, adaptive tracking, body sway, pupil size ratio, Visual analogs Scales Bond and Lader (VAS B&L) and Bowdle (VAS Bowdle)), pharmaco electroencephalogram (EEG), State-Trait Anxiety Inventory (STAI), The Dutch Temperament and 10 Character Inventory (TCI), The Dutch Personality Questionnaire-2-Revised (NPV-2-R), The Profile of Mood States (POMS), the Real-Time Intensity scale, and MINI. The time course that the patient experiences peak effects may also be assessed by the time the patient has a drug concentration in the blood of ≥ 40 ng / mL, for example, about 40 ng / mL, about 45 ng / mL, about 50 ng / mL, about 55 ng / mL, about 60 ng / mL, about 65 ng / mL, about 70 ng / mL, about 75 ng / mL, 15 about 80 ng / mL, about 85 ng / mL, about 90 ng / mL, about 95 ng / mL, about 100 ng / mL, about 105 ng / mL, about 110 ng / mL, about 115 ng / mL, about 120 ng / mL, about 125 ng / mL, about 130 ng / mL, about 135 ng / mL, about 140 ng / mL, about 145 ng / mL, about 150 ng / mL, or any range therebetween. The time course that the patient spends in the psychedelic state may also be assessed by the time the patient has a therapeutically relevant concentration of the drug in the blood, e.g., 20 the time that the patient has a drug concentration between about 20 ng / mL and about 150 ng / mL, for example, about 20 ng / mL, about 25 ng / mL, about 30 ng / mL, about 35 ng / mL, about 40 ng / mL, about 45 ng / mL, about 50 ng / mL, about 55 ng / mL, about 60 ng / mL, about 65 ng / mL, about 70 ng / mL, about 75 ng / mL, about 80 ng / mL, about 85 ng / mL, about 90 ng / mL, about 95 ng / mL, about 100 ng / mL, about 105 ng / mL, about 110 ng / mL, about 115 ng / mL, about 120 ng / mL, about 25 125 ng / mL, about 130 ng / mL, about 135 ng / mL, about 140 ng / mL, about 145 ng / mL, about 150 ng / mL, or any range therebetween. The Mystical Experiences Questionnaire was first developed during an online survey on psilocybin-containing mushrooms and validated using data from experimental studies with controlled doses of psilocybin. The revised version contains 30 items (MEQ30) regarding 30 subjective drug effects and is completed retrospectively. Effects are scored in total and on four subdomains (mystical, positive mood, space / time, ineffability), based on a percentage of maximum possible score. A Mystical Experience Questionnaire (MEQ30) score of greater than 153

[0114] 60%, the criteria for a complete mystical experience, has been shown to be a mediator of symptom improvement in previous psychedelic clinical trials. In some embodiments, the methods herein provide the patient with a Mystical Experience Questionnaire (MEQ30) score of at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%. In 5 some embodiments, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 90% of subjects treated with the methods described herein have a Mystical Experience Questionnaire (MEQ30) score of at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%. The 5-Dimensional Altered States of Consciousness Rating Scale (5D-ASC) measures 10 altered states of consciousness and contains 94 items (visual analog scales). The 5D-ASC scale measures alterations in mood, perception, experience of self in relation to environment, and thought disorder. The instrument consists of five subscales / dimensions and 11 lower-order scales. The 5D-ASC dimension “Oceanic Boundlessness” (27 items) measures derealization and depersonalization associated with positive emotional states, ranging from heightened mood to 15 euphoric exaltation. The corresponding lower-order scales include “experience of unity,” “spiritual experience,” “blissful state,” and “insightfulness.” The dimension “Anxious Ego Dissolution” (21 items) summarizes ego disintegration and loss of self-control phenomena associated with anxiety. The corresponding lower-order scales include “disembodiment,” “impaired control of cognition,” and “anxiety.” The dimension “Visionary Restructuralization”20 (18 items) consists of the lower-order scales “complex imagery,” “elementary imagery,” “audio- visual synesthesia,” and “changed meaning of percepts.” Two additional dimensions describe “Auditory Alterations” (15 items) and “Reduction of Vigilance” (12 items). Scoring is based on a percentage of maximum possible score. The scale is well-validated and widely used to characterize the subjective effects of various psychedelic drugs. In some embodiments, the 5D-ASC is used to 25 measure changes in the subjects’ subjective psychedelic experience. In some embodiments, the methods herein provide the patient with a 5D-ASC score (e.g., on the oceanic boundlessness subscale) of at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%. In some embodiments, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 90% of subjects treated with the methods 30 described herein have a 5D-ASC score (e.g., on the oceanic boundlessness subscale) of at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90%, at least 95%. 154

[0115] The Hallucinogen Rating Scale (HRS) is a questionnaire with up to 100 items, and the questionnaire is designed to assess the subjective effects of hallucinogenic substances. Participants rate responses to the majority of questions on a 5-point intensity scale: 0=not at all; 1=slightly; 2=moderately; 3=quite a bit; and 4=extremely. Some questions have a slightly modified scale, and 5 one question asks to rate the amount of time between when the drug was administered and feeling an effect from: no effect, 0-5 minutes, 5-15 minutes, 15-30 minutes, 30-60 minutes, or more than one hour. Questions are grouped into factors or domains including: 1) somaesthesia, 2) affect, 3) perception, 4) cognition, 5) volition, and 6) intensity. In some embodiments, the methods herein provide the patient with a Hallucinogen Rating Scale (HRS) score (e.g., on the intensity subscale) 10 of at least 1.8, at least 2.0, at least 2.2, at least 2.4, at least 2.6, at least 2.8, at least 3.0, at least 3.2, at least 3.4, at least 3.6, at least 3.8, or 4.0. In some embodiments, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 90% of subjects treated with the methods described herein have a score on the Intensity subscale of the HRS of greater than > 2.79, for example, a score of at least 2.8, at least 3.0, at least 3.2, at least 3.4, at least 3.6, at 15 least 3.8, or 4.0. The visual analogue scale (VAS) is a psychometric response scale that can be used in questionnaires. It is a measurement instrument for subjective characteristics or attitudes that cannot be directly measured. When responding to a VAS item, respondents specify their level of agreement to a statement by indicating a position along a continuous line between two end points, 20 usually a horizontal 100-mm line marked from “not at all,” “definitely not,” or the like, on the left to “extremely,” “definitely so,” or the like, on the right. The Bond and Lader VAS involves the subject indicating (with vertical marks) on sixteen horizontal 100-mm visual analogue scales how he / she feels. From these measurements, three main factors are calculated as described by Bond and Lader: alertness (from nine scores), contentedness (often called mood; from five scores), and 25 calmness (from two scores). The Bowdle VAS and Drug Rating VAS provides the subject with items of the drug rating questionnaire: feel drug, like drug, and dislike drug. The VAS any drug effect involves the subject indicating (with vertical marks) on horizontal 100-mm visual analogue scales with the any drug effects item (“I can feel any drug effect”). In some embodiments, the subject has a maximum VAS score (e.g., Bond and Lader VAS, Bowdle VAS and Drug Rating 30 VAS, and / or VAS any drug effect) of > 60 mm or ≥ 70 mm after treatment. In some embodiments the subject has a VAS score (e.g., Bond and Lader VAS, Bowdle VAS and Drug Rating VAS, and / or VAS any drug effect) of greater than or equal to 60 mm, 65 mm, 70 mm, 75 mm, 80 mm, 155

[0116] 85 mm, 90 mm, or 95 mm, after treatment. In some embodiments, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 85%, at least 90% of subjects treated with the methods described herein report a maximum VAS score (e.g., Bond and Lader VAS, Bowdle VAS and Drug Rating VAS, and / or VAS any drug effect) of greater than or 5 equal to 60 mm, 65 mm, 70 mm, 75 mm, 80 mm, 85 mm, 90 mm, or 95 mm following treatment. In some embodiments, following treatment, the subject experiences a VAS any drug effect score of ≥ 70 mm for a duration of about 30 minutes, about 35 minutes, about 40 minutes, about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 10 minutes, about 100 minutes, about 105 minutes, about 110 minutes, about 115 minutes, about 120 minutes, or any range therebetween, such as from about 30 to about 120 minutes, from about 30 to about 45 minutes, from about 40 to about 100 minutes, from about 45 to about 90 minutes, from about 50 to about 75 minutes, from about 60 to about 70 minutes. The 5-item Persisting Effects Questionnaire (PEQ) is a 5-item questionnaire that assesses 15 the meaningfulness, spiritual significance, psychological insightfulness, and how psychologically challenging a participant experience was during the medicine session. Scores are assessed on a scale from 0 (not at all) to 5 (extremely). Higher scores (under consideration of reverse-scored items) indicate stronger persisting treatment effects. In some embodiments, the patient reports their experience as the most or among the top five most meaningful experiences of their life according 20 to the Persisting Effects Questionnaire (PEQ). In some embodiments, the patient reports their experience as the most or among the top five most psychologically insightful experiences of their life, according to the Persisting Effects Questionnaire (PEQ). The Profile of Mood States (POMS) measures six identifiable mood- or affective states: Tension-Anxiety, Depression-Rejection, Anger-Hostility, Vigor-Activity, and Fatigue-Inertia. In 25 the original POMS, these states are addressed through 65 five-point adjective rating scales, and a sixth dimension (confusion-bewilderment) is added that does not appear in the abbreviated POMS wherein 32 questions are used to assess different periods (usually past two hours, sometimes past week). The scales use a five-point score system, ranging from 0 (not at all) to 4 (extremely). The scores of the different states are calculated using a scoring algorithm. 30 In the Real-Time Intensity scale, subjects are asked to verbally rate the psychological intensity of their experience on a scale from 0-4 (0 = not at all; 1 = slightly; 2 = moderately; 3 very much; 4 = extremely) on three levels: visual intensity, bodily intensity, and 156

[0117] emotional / metacognitive intensity. Their answers are recorded during the drug administration (during the experience). In some embodiments, the methods herein provide the patient with a Real- Time Intensity scale score (e.g., on the emotional / metacognitive subscale) of at least 1.8, at least 2.0, at least 2.2, at least 2.4, at least 2.6, at least 2.8, at least 3.0, at least 3.2, at least 3.4, at least 5 3.6, at least 3.8, or 4.0. In some embodiments, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, at least 75%, at least 80%, at least 90% of subjects treated with the methods described herein have a score on the Real-Time Intensity scale of greater than > 2.79, for example, a score of at least 2.8, at least 3.0, at least 3.2, at least 3.4, at least 3.6, at least 3.8, or 4.0. In some embodiments, the pharmaceutical formulation provides a controlled-release of the 10 psychopharmaceutical agent such as a tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) following bolus injection, including bolus subcutaneous injection, which achieves an onset of effects within about 30 minutes, about 25 minutes, about 20 minutes, about 15 minutes, about 10 minutes post administration, such as from about 1 minute to about 30 minutes, about 5 minutes to about 25 minutes, about 10 minutes to 15 about 20 minutes, about 15 minutes to about 30 minutes, about 5 minutes to about 10 minutes. In some embodiments, the pharmaceutical formulation provides a controlled-release of the psychopharmaceutical agent such as a tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) following bolus injection, including bolus subcutaneous injection, which achieves an offset of effects of greater than about 35 minutes and 20 up to about 180 minutes post administration, such as about 35 minutes, about 40 minutes, about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 minutes, about 100 minutes, about 105 minutes, about 110 minutes, about 115 minutes, about 120 minutes, about 125 minutes, about 130 minutes, about 135 minutes, about 140 minutes, about 145 25 minutes, about 150 minutes, about 160 minutes, about 170 minutes, about 180 minutes, post administration, or any range therebetween. In some embodiments, the pharmaceutical formulation provides a controlled-release of the psychopharmaceutical agent such as a tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) following bolus injection, including bolus 30 subcutaneous injection, with a drug concentration in the blood of ≥ 40 ng / mL, corresponding to peak psychedelic effects. For example, following bolus injection, including bolus subcutaneous injection, the pharmaceutical formulation may provide a drug concentration in the blood of about 157

[0118] 40 ng / mL, about 45 ng / mL, about 50 ng / mL, about 55 ng / mL, about 60 ng / mL, about 65 ng / mL, about 70 ng / mL, about 75 ng / mL, about 80 ng / mL, about 85 ng / mL, about 90 ng / mL, about 95 ng / mL, about 100 ng / mL, about 105 ng / mL, about 110 ng / mL, about 115 ng / mL, about 120 ng / mL, about 125 ng / mL, about 130 ng / mL, about 135 ng / mL, about 140 ng / mL, about 145 ng / mL, about 5 150 ng / mL, or any range therebetween. For maximum therapeutic benefits and clinical scalability, these drug concentrations (and thus peak effects) are preferably provided for a duration of about 30 minutes, about 35 minutes, about 40 minutes, about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 minutes, about 100 minutes, about 105 10 minutes, about 110 minutes, about 115 minutes, about 120 minutes, or any range therebetween. In some embodiments, the pharmaceutical formulation provides a controlled-release of the psychopharmaceutical agent such as a tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) following bolus injection, including bolus subcutaneous injection, which places the subject into a psychedelic state with a therapeutically 15 relevant concentration of the drug in the blood of about 20 ng / mL, about 25 ng / mL, about 30 ng / mL, about 35 ng / mL, about 40 ng / mL, about 45 ng / mL, about 50 ng / mL, about 55 ng / mL, about 60 ng / mL, about 65 ng / mL, about 70 ng / mL, about 75 ng / mL, about 80 ng / mL, about 85 ng / mL, about 90 ng / mL, about 95 ng / mL, about 100 ng / mL, about 105 ng / mL, about 110 ng / mL, about 115 ng / mL, about 120 ng / mL, about 125 ng / mL, about 130 ng / mL, about 135 ng / mL, about 20 140 ng / mL, about 145 ng / mL, about 150 ng / mL, or any range therebetween, such as from about 20 to about 150 ng / mL, or from about 30 to about 100 ng / mL, or from about 60 to about 100 ng / mL or from about 40 to about 80 ng / mL, or from about 45 to about 60 ng / mL, or from about 60 to about 80 ng / mL, or from about 50 to about 80 ng / mL. The psychedelic state and therapeutically relevant concentration of the drug may last for about 35 minutes, about 40 minutes, 25 about 45 minutes, about 50 minutes, about 55 minutes, about 60 minutes, about 65 minutes, about 70 minutes, about 75 minutes, about 80 minutes, about 85 minutes, about 90 minutes, about 95 minutes, about 100 minutes, about 105 minutes, about 110 minutes, about 115 minutes, about 120 minutes, about 130 minutes, about 140 minutes, about 150 minutes, about 160 minutes, about 170 minutes, about 180 minutes, or any range therebetween. 30 Further, desirable pharmaceutical formulations provide a controlled-release of the tryptamine psychedelic (e.g., a pharmaceutically acceptable salt of a compound of Formula (I) through (III)) following bolus injection, including bolus subcutaneous injection, to achieve the 158

[0119] aforementioned duration of peak effects and / or psychedelic state time course, but do so without a burst release of the tryptamine psychedelic exceeding maximum plasma levels (Cmax) of about 200 ng / mL, about 195 ng / mL, about 190 ng / mL, about 185 ng / mL, about 180 ng / mL, about 175 ng / mL, about 170 ng / mL, about 165 ng / mL, about 160 ng / mL, or about 155 ng / mL. Consequently, 5 pharmaceutical formulations of the present disclosure, and in particular subcutaneous pharmaceutical formulations of the present disclosure, provide a smoother, more controlled delivery of the psychopharmaceutical agent contained therein compared to bolus I...

Claims

CLAIMS 1. An injectable pharmaceutical formulation, comprising: a psychopharmaceutical agent; a hyaluronate salt; and 5 an aqueous vehicle; wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of a compound of Formula (I) or a stereoisomer, solvate, or prodrug thereof, wherein: 10 X1and X2are independently selected from the group consisting of hydrogen, deuterium, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; Y1and Y2are independently selected from the group consisting of hydrogen and 15 deuterium; R2is selected from the group consisting of hydrogen, deuterium, halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; 20 R4and R5are independently selected from the group consisting of hydrogen, deuterium, hydroxyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkoxy, unsubstituted or substituted alkylthio, and unsubstituted or substituted acyloxy; R6and R7are independently selected from the group consisting of hydrogen, deuterium, 291halogen, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl; and R8 and R9 are independently selected from the group consisting of hydrogen, deuterium, 5 unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted cycloalkyl, unsubstituted or substituted heterocycloalkyl, unsubstituted or substituted aryl, and unsubstituted or substituted heteroaryl, or alternatively R8 and R9 together with the nitrogen atom attached thereto are optionally joined to form an unsubstituted or substituted heterocycloalkyl. 10 2. The injectable pharmaceutical formulation of claim 1, wherein the compound has a structure of Formula (II), or a stereoisomer, solvate, or prodrug thereof wherein: 15 X1and X2are independently hydrogen or deuterium, Y1 and Y2 are independently hydrogen or deuterium, each Z1 is independently hydrogen or deuterium, each Z2is independently hydrogen or deuterium, and R2, R4, R5, R6, and R7are independently hydrogen or deuterium. 20 3. The injectable pharmaceutical formulation of claim 1, wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of at least one compound selected from the group consisting of 292(I-9), (I-10), (I-11), and (I-12), or a stereoisomer, solvate, or prodrug thereof. 5 4. The injectable pharmaceutical formulation of claim 1, wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2,2-d4 (I-8).

5. The injectable pharmaceutical formulation of claim 1, wherein the10 psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1-d2 (I-6).

6. The injectable pharmaceutical formulation of claim 1, wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N- 15 dimethylethan-1-amine-1,1-d2(I-2).

7. The injectable pharmaceutical formulation of claim 1, wherein the psychopharmaceutical agent is an active salt mixture comprising: (i) a pharmaceutically acceptable salt of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8); and (ii) a 294pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1- amine-1,2,2-d3(I-10) and / or 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11).

8. The injectable pharmaceutical formulation of claim 7, wherein the active salt mixture 5 comprises (i) from 60% to 99% by weight of the pharmaceutically acceptable salt of 2-(1H-indol- 3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-8), based on a total weight of the active salt mixture; and (ii) from 1% to 40% by weight, in sum, of the pharmaceutically acceptable salt of one or more of 2-(1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,2,2-d3 (I-10) and / or 2-(1H- indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-11), based on a total weight of the active 10 salt mixture.

9. The injectable pharmaceutical formulation of claim 1, wherein the compound has a structure of Formula (III), or a stereoisomer, solvate, or prodrug thereof15 wherein: X1 and X2 are independently hydrogen or deuterium, Y1 and Y2 are independently hydrogen or deuterium, each Z1is independently hydrogen or deuterium, each Z2is independently hydrogen or deuterium, 20 each Z3 is independently hydrogen or deuterium, and R2, R4, R6, and R7 are independently hydrogen or deuterium.

10. The injectable pharmaceutical formulation of claim 1, wherein the 295psychopharmaceutical agent is a pharmaceutically acceptable salt of at least one compound selected from the group consisting of 5stereoisomer, solvate, or prodrug thereof.

11. The injectable pharmaceutical formulation of claim 1, wherein the 5 psychopharmaceutical agent is a pharmaceutically acceptable salt of 2-(5-methoxy-1H-indol-3- yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-20).

12. The injectable pharmaceutical formulation of claim 1, wherein the psychopharmaceutical agent is an active salt mixture comprising: (i) a pharmaceutically acceptable 10 salt of 2-(5-methoxy-1H-indol-3-yl)-N,N-bis(methyl-d3)ethan-1-amine-1,1,2,2-d4(I-20); and (ii) a pharmaceutically acceptable salt of one or more of 2-(5-methoxy-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,2,2-d3(I-22) and / or 2-(5-methoxy-1H-indol-3-yl)-N,N- bis(methyl-d3)ethan-1-amine-1,1,2-d3(I-23). 15 13. The injectable pharmaceutical formulation of claim 1, wherein the pharmaceutically acceptable salt is a fumarate, a benzoate, a salicylate, a succinate, an oxalate, a glycolate, a hemi- oxalate, or a hemi-fumarate salt.

14. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the 20 psychopharmaceutical agent by weight (in terms of free base equivalence) per total volume of the pharmaceutical formulation is about 1 mg / mL to about 100 mg / mL.

15. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the psychopharmaceutical agent by weight (in terms of free base equivalence) per total volume of the 25 pharmaceutical formulation is about 10 mg / mL to about 50 mg / mL.

16. The injectable pharmaceutical formulation of claim 1, wherein the hyaluronate salt is 299sodium hyaluronate.

17. The injectable pharmaceutical formulation of claim 1, wherein the hyaluronate salt has a weight average molecular weight of about 500 kDa to about 2,000 kDa. 5 18. The injectable pharmaceutical formulation of claim 1, wherein the hyaluronate salt has a weight average molecular weight of about 1,000 kDa to about 1,800 kDa.

19. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the 10 hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 2% (w / v).

20. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% 15 to about 1% (w / v).

21. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 0.75% (w / v). 20 22. The injectable pharmaceutical formulation of claim 1, wherein a concentration of the hyaluronate salt by weight per total volume of the pharmaceutical formulation is from about 0.1% to about 0.5% (w / v). 25 23. The injectable pharmaceutical formulation of claim 1, which has a pH of about 3 to about 7.

24. The injectable pharmaceutical formulation of claim 1, which has an osmolality of about 150 mOsm / kg to about 600 mOsm / kg. 30 25. The injectable pharmaceutical formulation of claim 1, which has a viscosity of less than about 3,000 cP. 30026. The injectable pharmaceutical formulation of claim 1, which is suitable for subcutaneous injection. 5 27. The injectable pharmaceutical formulation of claim 1, which is suitable for bolus subcutaneous injection.

28. The injectable pharmaceutical formulation of claim 1, wherein the injectable pharmaceutical formulation provides a duration of peak effects of about 30 minutes to about 120 10 minutes after being administered to a human subject via bolus subcutaneous injection.

29. A kit suitable for preparing the injectable pharmaceutical formulation of claim 1, the kit comprising: (a1) a first solution comprising the psychopharmaceutical agent and the aqueous vehicle; 15 and (b1) a second solution comprising the hyaluronate salt and the aqueous vehicle.

30. A method of treating a central nervous system (CNS) disorder and / or psychological disorder in a subject in need thereof, comprising administering to the subject a therapeutically 20 effective amount of the injectable pharmaceutical formulation of claim 1.

31. The method of claim 30, wherein the CNS disorder and / or psychological disorder is a substance use disorder. 25 32. The method of claim 31, wherein the substance use disorder is alcohol use disorder.

33. The method of claim 30, wherein the CNS disorder and / or psychological disorder is an anxiety disorder. 30 34. The method of claim 33, wherein the anxiety disorder is generalized anxiety disorder (GAD). 30135. The method of claim 34, wherein the generalized anxiety disorder is comorbid with depression.

36. The method of claim 33, wherein the anxiety disorder is social anxiety disorder. 5 37. The method of claim 30, wherein the CNS disorder and / or psychological disorder is a depressive disorder.

38. The method of claim 37, wherein the depressive disorder is major depressive disorder 10 (MDD) or treatment-resistant depression (TRD).

39. The method of claim 30, wherein the CNS disorder and / or psychological disorder is at least one selected from the group consisting of post-traumatic stress disorder (PTSD), major depressive disorder (MDD), treatment-resistant depression (TRD), suicidal ideation, suicidal 15 behavior, melancholic depression, atypical depression, dysthymia, non-suicidal self-injury disorder (NSSID), bipolar and related disorders, obsessive-compulsive disorder (OCD), generalized anxiety disorder (GAD), acute psychedelic crisis, social anxiety disorder, alcohol use disorder, opioid use disorder, amphetamine use disorder, nicotine use disorder, cocaine use disorder, Alzheimer’s disease, cluster headache and migraine, attention deficit hyperactivity 20 disorder (ADHD), pain, aphantasia, childhood-onset fluency disorder, major neurocognitive disorder, mild neurocognitive disorder, chronic fatigue syndrome, Lyme disease, gambling disorder, anorexia nervosa, bulimia nervosa, binge-eating disorder, pedophilic disorder, exhibitionistic disorder, voyeuristic disorder, fetishistic disorder, sexual masochism or sadism disorder, transvestic disorder, sexual dysfunction, and obesity. 25 40. The method of claim 30, wherein the injectable pharmaceutical formulation is administered via injection.

41. The method of claim 30, wherein the injectable pharmaceutical formulation is 30 administered via subcutaneous injection.

42. The method of claim 30, wherein the injectable pharmaceutical formulation is 302administered via bolus subcutaneous injection.

43. The method of claim 42, wherein the bolus subcutaneous injection provides a duration of peak effects of about 30 minutes to about 120 minutes after being administered. 5 44. An injectable pharmaceutical formulation, comprising: a psychopharmaceutical agent; a hyaluronate salt; and an aqueous vehicle; 10 wherein the psychopharmaceutical agent is a pharmaceutically acceptable salt of ketamine, or a stereoisomer, solvate, or prodrug thereof.

45. The injectable pharmaceutical formulation of claim 44, wherein the pharmaceutically acceptable salt is an inorganic salt. 15 46. The injectable pharmaceutical formulation of claim 44, wherein the pharmaceutically acceptable salt is a hydrochloride salt.

47. A kit suitable for preparing the injectable pharmaceutical formulation of claim 44, the 20 kit comprising: (a1) a first solution comprising the psychopharmaceutical agent and the aqueous vehicle; and (b1) a second solution comprising the hyaluronate salt and the aqueous vehicle. 25 48. A method of treating a central nervous system (CNS) disorder and / or psychological disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the injectable pharmaceutical formulation of claim 44. 303

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