Crystalline salts of oxanoribogaine

Abstract

The present disclosure relates to various crystalline salts and polymorphs of oxanoribogaine, which are useful for treating psychiatric disorders, including substance use disorders. These salts include the hydrochloride salts, fumarate salts, phosphate salts, and p-toluenesulfonate salts thereof.

Description

[0001]CRYSTALLINE SALTS OF OXANORIBOGAINE FIELD OF THE DISCLOSURE The present disclosure relates to various crystalline salts and polymorphs of oxanoribogaine, which are useful for treating psychiatric disorders, including substance use disorders. BACKGROUND OF THE DISCLOSURE Ibogaine (Scheme 1) is a natural alkaloid isolated from the African plant Tabernanthe iboga. Extensive preclinical and clinical data support the effectiveness of ibogaine in treating substance use disorders, including those involving opioids, psychostimulants, and alcohol. Noribogaine (Scheme 1) is the major active metabolite of ibogaine both preclinically and clinically and is believed to be a major contributor to ibogaine’s efficacy in treating substance use disorders. Consistent with this, noribogaine demonstrates similar activity to ibogaine in preclinical models of substance use disorders. Naturally occurring ibogaine occurs as a single, levorotatory isomer, as pictured in Scheme 1. Similarly, noribogaine produced as a metabolite of naturally derived ibogaine is also a single levorotatory isomer, as pictured in Scheme 1. Scheme 1. Structures of ibogaine and noribogaine. Oxanoribogaine (7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9-methanobenzofuro[2,3- d]pyrido[1,2-a]azepin-2-ol) is an analog of noribogaine wherein the indole NH has been replaced by an oxygen atom to form a benzofuran ring system. The compound occurs as two enantiomers, (-)-oxanoribogaine [(6R,6aS,7S,9R)-7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9- methanobenzofuro[2,3-d]pyrido[1,2-a]azepin-2-ol] and (+)-oxanoribogaine [(6R,6aS,7S,9R)- 7-ethyl-6,6a,7,8,9,10,12,13-octahydro-6,9-methanobenzofuro[2,3-d]pyrido[1,2-a]azepin-2- ol], which are pictured below in Scheme 2 as compounds 1A and 1B, respectively. Compound 1A is the pharmacologically more active enantiomer. Scheme 2. Structures of oxanoribogaine enantiomers with atom numbering indicated on the (-)-oxanoribogaine structure. The racemate of oxanoribogaine, herein designated rac-oxanoribogaine, or 1, consists of a 50:50 molar ratio mixture of the two enantiomers 1A (also referred to interchangeably as E2) and 1B (also referred to interchangeably as E1). Throughout the present disclosure, it is to be understood that the term oxanoribogaine when listed without a specific stereochemical modifier is intended to refer interchangeably to the racemate, either enantiomer, or any mixture of the two enantiomers (scalemic mixtures). In preclinical models of opioid use disorder, rac-oxanoribogaine and its more active enantiomer (-)-oxanoribogaine demonstrate potent efficacy in suppressing opioid self- administration, suggesting their potential efficacy in treating opioid use disorder. This activity is of greater potency than that of noribogaine. Furthermore, in preclinical models, rac-oxanoribogaine and (-)-oxanoribogaine demonstrate substantially improved cardiac safety compared to noribogaine. Accordingly, these compounds may be useful in treating opioid use disorder or other substance use disorders without the dangerous cardiac side effects of ibogaine and noribogaine. US Patent No.11,840,541, the contents of which are incorporated herein by reference, discloses, in part, oxanoribogaine and analogs thereof. International patent application PCT / US2022 / 016757, the contents of which are incorporated herein by reference, discloses, in part, methods of using oxanoribogaine and analogs thereof in treating substance use disorders. Many compounds may exist in more than one salt form and those salts in turn may each exist in more than one crystal form, or polymorph. Relative to one another, these salts and polymorphs exhibit different physical, chemical, and spectroscopic properties. For example, certain salts or polymorphs of a compound may be more chemically stable, may be more readily crystallized, may be more readily soluble in particular solvents, may be more or less hygroscopic, may flow more readily, or may compress more easily than others. See, e.g., P. DiMartino, et al., J. Thermal Anal.,48:447-458 (1997). In the case of drugs, certain solid forms may be more bioavailable than others, while others may be more stable under certain manufacturing, storage, and biological conditions. This is particularly important from a regulatory standpoint, since drugs are approved by governmental agencies, such as the U.S. Food and Drug Administration, only if they meet exacting purity and characterization standards. Indeed, the regulatory approval of one salt or polymorph of a compound, which exhibits certain solubility and physicochemical (including spectroscopic) properties, does not necessarily imply the ready approval of other salts or polymorphs of that same compound. Salt and polymorphic forms of a compound are known in the pharmaceutical arts to affect, for example, the solubility, stability, flowability, fractability, and compressibility of the compound, as well as the safety and efficacy of drug products comprising it. See, e.g., Knapman, K. Modern Drug Discoveries, 2000, 53. Therefore, the discovery of new salts and polymorphs of a drug can provide a variety of advantages. However, finding the appropriate conditions for preparing and crystallizing a new salt or polymorph of a particular compound is tedious and often involves trial and error, as many factors come into play to find the right conditions for the synthesis and crystallization thereof. For example, solvent, concentration, temperature, heating or cooling rate, stoichiometry of reactants, addition rates, and mixing parameters must all be varied to obtain the desired result. This present disclosure encompasses polymorphs of certain salts of oxanoribogaine and stereoisomers thereof, such as (-)-oxanoribogaine. Further, as described hereinbelow, it has now been discovered that certain salts of oxanoribogaine and stereoisomers thereof, such as salts of (-)-oxanoribogaine, can be prepared and isolated in a number of crystal forms. SUMMARY OF THE DISCLOSURE The present disclosure relates to various crystalline salts and polymorphs of oxanoribogaine, which are useful for treating psychiatric disorders, including substance use disorders. These salts include the hydrochloride salts, fumarate salts, phosphate salts, and p- toluenesulfonate salts thereof. In addition, the present disclosure relates to polymorphs of the aforementioned salts in crystalline form. BRIEF DESCRIPTION OF THE DRAWINGS The objects, features, and advantages of the present disclosure will become apparent to one of ordinary skill in the art, in view of the following detailed description, taken in combination with the attached drawings, in which: FIG.1. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine HCl Form A. FIG.2. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine HCl Form A. FIG.3. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine HCl Form B. FIG.4. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine HCl Form C. FIG.5. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine HCl Form C. FIG.6. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine HCl Form D. FIG.7. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine HCl Form D. FIG.8. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine hemifumarate Form A. FIG.9. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine hemifumarate Form A. FIG.10. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine phosphate Form A. FIG.11. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine phosphate Form A. FIG.12. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine p-toluenesulfonate Form A. FIG.13. Depicts an exemplary DSC thermogram of (-)-oxanoribogaine p-toluenesulfonate Form A. FIG.14. Depicts an exemplary XRPD diffractogram of rac-oxanoribogaine HCl Form A. FIG.15. Depicts an exemplary DSC thermogram of rac-oxanoribogaine HCl Form A. FIG.16. Depicts an exemplary XRPD diffractogram of rac-oxanoribogaine HCl Form B. FIG.17. Depicts an exemplary DSC thermogram of rac-oxanoribogaine HCl Form B. FIG.18. Depicts an exemplary XRPD diffractogram of rac-oxanoribogaine hemifumarate Form A. FIG.19. Depicts an exemplary DSC thermogram of rac-oxanoribogaine hemifumarate Form A. FIG.20. Depicts an exemplary XRPD diffractogram of rac-oxanoribogaine phosphate Form A. FIG.21. Depicts an exemplary DSC thermogram of rac-oxanoribogaine phosphate Form A. FIG.22. Depicts an exemplary XRPD diffractogram of rac-oxanoribogaine p- toluenesulfonate Form A. FIG.23. Depicts an exemplary DSC thermogram of rac-oxanoribogaine p-toluenesulfonate Form A. FIG.24. Depicts an exemplary XRPD diffractogram of (-)-oxanoribogaine free base Form A. DETAILED DESCRIPTION OF THE DISCLOSURE The salts disclosed herein include at least one asymmetric center. When the stereoisomers are specifically designated, these centers are specifically indicated by the symbols "R" or "S," depending on the configuration of substituents around the chiral atom. However, when stereochemistry is not to be designated, the structures will be drawn without indicating the stereochemistry; these structures are racemic mixtures. In some embodiments, a composition prepared herein may be enriched in a specific enantiomer of any compound disclosed herein relative to the corresponding opposite enantiomer of that compound, such that the mixture is not racemic. In such cases, the subject mixture of isomers is understood to have an enantiomeric excess and optical purity >0%. The enantiomeric excess or optical purity of the isomeric mixture may be, for example, >0%, >5%, >25%, >50%, >75%, >90%, >95%, >97%, >98%, or >99%. The enantiomeric excess or optical purity of the isomeric mixture may be, for example, 5-100%, 25-100%, 50-100%, 75-100%, 90-100%, 95-100%, 97-100%, 98-100%, or 99-100%. Thus, for example, contemplated herein is a composition including the S enantiomer of a compound substantially free of the R enantiomer, or the R enantiomer substantially free of the S enantiomer. Further, if the named compound includes more than one chiral center, the scope of the present disclosure also includes compositions containing the various stereoisomers and diastereomers, including mixtures of varying proportions between the various stereoisomers and / or diastereomers or pharmaceutically acceptable salts thereof, as well as compositions including one or more stereoisomers and diastereomers substantially free of one or more of the other stereoisomers and / or diastereomers, respectively. By “substantially free” in this context, it is meant that the composition includes less than, for example, 50%, 25%, 15%, 10%, 8%, 5%, 3%, 2%, or 1% of the minor enantiomer or diastereomer(s). For example, the expression that a compound is enantiomerically pure refers to the compound being substantially free of other stereoisomers, including any other enantiomers or diastereomers. For clarity, in the context of the present disclosure, chemical structures of a compound depicted with a specific stereochemical orientation at any particular chiral center, as defined by wedge and dash notation or other three-dimensional representation, are intended to represent the specified stereoisomer of said compound in substantially pure form, or a mixture enriched in the stereoisomer(s) with the specified stereochemical orientation at the defined chiral center over the stereoisomer(s) with the opposite orientation at said chiral center. As used herein, the term that the “composition is substantially free,” as relates to a polymorph, refers to the composition being predominantly present in a particular polymorph relative to other possible polymorphs. For example, (-)-oxanoribogaine HCl exists in four solid forms, Forms, A, B, C, and D. The statement that (-)-oxanoribogaine HCl exists in Form A substantially free from Forms B, C, and D means that the Form A polymorph is the predominant polymorph present relative to Forms B, C, and D, i.e., the Form A polymorph is present in excess relative to the Form B, C, and D polymorphs. By “substantially free” of Form B, C, and D relative to Form A, it is meant that the composition includes less than, for example, 50%, 25%, 15%, 10%, 8%, 5%, 3%, 2%, or 1% of the Form B, C, and D polymorphs relative to the Form A polymorph. The terms "about" or "approximately" as used herein mean within an acceptable error range for the particular value as determined by one of ordinary skill in the art, which will depend in part on how the value is measured or determined, i.e., the limitations of the measurement system. For example, "about" can mean within 3 or more than 3 standard deviations, per the practice in the art. Alternatively, "about" can mean a range of up to 20%, a range of up to 10%, a range of up to 5%, and / or a range of up to 1% of a given value. Alternatively, particularly with respect to biological systems or processes, the term can mean within an order of magnitude, e.g., within 5-fold, or within 2-fold, of a value. “About” and “approximately” are used interchangeably herein. As defined herein, an “inert solvent” is a solvent that does not react with either the reactants or products formed in the reaction. Suitable organic solvents for use in the present disclosure include, but are not limited to, alcohols having 1-6 carbon atoms, such as methanol, ethanol, isopropanol, butanol and the like; ketones having 1-6 carbon atoms, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and the like; ether solvents having 1- 6 carbon atoms, such as dimethyl ether, diethyl ether, methyl ethyl ether, methyl t-butyl ether MTBE, dipropyl ether, diisopropyl ether and the like, cyclic ethers having 4-6 carbon atoms, such as THF, dioxane, and the like; halogenated solvents such as dichloroethane, dichloromethane, chloroform and the like; esters having 2-10 carbon atoms, such as ethyl acetate, isopropyl acetate, n-propyl acetate and the like; nitriles such as acetonitrile, propionitrile and the like; hydrocarbons having 1-10 carbon atoms, including aryl groups, such as toluene, xylene, cyclohexane, heptane, xylene and the like; dimethylsulfoxide (DMSO), N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMA) and the like; and mixtures thereof in various proportion without limitation. The use of a suitable solvent includes the use of a mixture of solvents. The applicability of a particular solvent for a reaction is dependent on several factors, such as the type of reaction, the reactants, the products, reagents used, and the like. One of ordinary skill in the art can determine the appropriate solvents for the reactions described herein. As used herein, the term “protic” refers to a proton or a hydrogen atom or ion. The term “protic solvent,” as used herein, refers to a polar liquid compound that has dissociable hydrogen atoms and is capable of forming a hydrogen bond with oxygen, fluorine, or nitrogen atoms. The term “protic polar solvent,” as used herein, refers to a solvent that has at least one OH or NH bond and is miscible with water. Examples include water, methanol, ethanol, ammonia, and the like. XRPD patterns of polymorphs are depicted herein. Each polymorph is characterized by or has an XPRD pattern substantially as shown in its corresponding aforementioned figure, e.g., at least 70% of the XPRD pattern has the peaks at the values shown with variations of ±0.50 °2θ, and in another embodiment, at least 75% of the XPRD pattern has the peaks at the values shown with variations of ±0.50 °2θ, and in another embodiment, at least 80% of the XPRD pattern has the peaks at the values shown with variations of ±0.50 °2θ, and in a still further embodiment, at least 85% of the XPRD pattern has the peaks at the values shown with variations of ±0.50 °2θ, and in still another embodiment, at least 90% of the XPRD pattern has the peaks at the values shown with variations of ±0.50 °2θ. It should be understood, however, that relative intensities and assignment of the peaks of polymorphic forms depicted in these figures can vary depending on a number of factors, including, without limitation, sample preparation, aspect ratio, particle size, mounting, and the instrument and analytical procedure and settings used to obtain the spectrum. As such, the peaks observed in the figures and assignments listed herein in the various tables and figures are intended to encompass variations of ±0.5 °2θ and variations in relative peak intensity understood to be acceptable by one skilled in the art. However, it is to be understood that peak values in the tables and figures also encompass variations of ±0.1, ±0.2, ±0.3, and ±0.4 °2θ, or any value therein between. When listing the peaks for the XRPDs, it is to be understood that each of the values listed are ±0.50 °2θ, even when ±0.50 °2θ is not recited in the listing. Further, when a listing of peaks is provided with a variation at the end of the list, e.g., ±0.50 °2θ, for purposes of this disclosure, each value in the list of peaks is modified by the listed variation, e.g. ±0.50 °2θ. In other embodiments, the depicted or listed XRPD peaks have variations of between ±1 °2θ and ±0 °2θ, e.g., ±1 °2θ, ±0.75 °2θ, ±0.20 °2θ, or ±0.10 °2θ. Unless indicated to the contrary, the term “freebase” or “free base” refers to oxanoribogaine in its base, unprotonated form without any counterion, or one of its enantiomers, if indicated, e.g., (-)-oxanoribogaine freebase or (+)-oxanoribogaine freebase. As defined herein, the term “solvent” refers to a liquid substance or a mixture of liquid substances, which is capable of dissolving another substance (solute) to form a solution in which the solute is uniformly dispersed at the molecular or ionic size level. For purposes of this disclosure, the solvent may be a reaction solvent or a crystallizing solvent. Solvents referenced herein are inert solvents with respect to the solutes or reactants. As defined herein, an “inert solvent” is a solvent that does not react with either the reactants or products formed in a chemical reaction. The term “reaction solvent” or like term is a solvent in which a chemical reaction occurs. It is an inert solvent, i.e., it does not react with either the free base or the acids or the product that is formed. In an embodiment, the free base and the acid are soluble therein, and the product salt may or may not be soluble therein. Further, in an embodiment, it is a volatile solvent. Further, in an embodiment, it is a volatile solvent, which has a boiling point of 90oC or less at 1 atm pressure. As used herein, the term “crystallizing solvent” or like term is an inert solvent that is used for the crystallization of a salt of the present disclosure in which the salt is poorly soluble at room temperature or low temperature, but in which it is more soluble when heated, for example, to the boiling point of the solvent. Ideally, the salt is nearly insoluble or sparingly soluble in the solvent at room temperature and extremely soluble at the boiling point of the solvent. The crystallizing solvent may be one solvent or a mixture of solvents. If it is a mixture of liquid solvents, they may be miscible. In an embodiment, water may be a solvent or co-solvent. The term “recrystallizing solvent”, as used herein, is a crystallizing solvent, and the two terms may be used interchangeably. The term “crystalline” as applied to a compound refers to a solid phase in which the material has a regularly ordered internal structure at the molecular level and gives a distinctive X-ray diffraction pattern with defined peaks. By substantially crystalline, it is meant that the composition has greater than 50%, or greater than 55%, or greater than 60%, or greater than 65%, or greater than 70%, or greater than 75%, or greater than 80%, or greater than 85%, or greater than 90%, or greater than 95%, or greater than 99% of the compound present in crystalline form. The term “crystallization”, as used throughout this disclosure, can refer to crystallization and / or recrystallization, depending upon the applicable circumstances relating to the preparation of the salts described herein. As used herein and unless otherwise indicated, the terms "polymorph” and “polymorphic form” refer to solid crystalline forms of a compound or complex. Different polymorphs of the same compound can exhibit different physical, chemical, and / or spectroscopic properties. Different physical properties include, but are not limited to, stability (e.g., to heat or light), compressibility and density (important in formulation and product manufacturing), and dissolution rates (which can affect bioavailability). Differences in stability can result from changes in chemical reactivity (e.g., differential oxidation, such that a dosage form discolors more rapidly when comprised of one polymorph than when comprised of another polymorph) or mechanical characteristics (e.g., tablets crumble on storage as a kinetically favored polymorph converts to a thermodynamically more stable polymorph) or both (e.g., tablets of one polymorph are more susceptible to breakdown at high humidity). Different physical properties of polymorphs and / or salts can affect their processing. For example, one polymorph might be more likely to form solvates or might be more difficult to filter or wash free of impurities than another due to, for example, the shape or size distribution of particles of it. Polymorphs of a molecule can be obtained by a number of methods known in the art. Such methods include, but are not limited to, melt recrystallization, melt cooling, solvent crystallization, desolvation, rapid evaporation, rapid cooling, slow cooling, vapor diffusion and sublimation. Polymorphs can be detected, identified, classified, and characterized using well-known techniques such as, but not limited to, melting point, differential scanning calorimetry (DSC), thermogravimetry(TGA), X-ray powder diffractometry (XRPD), single crystal X-ray diffractometry, vibrational spectroscopy, solution calorimetry, solid state nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, Raman spectroscopy, hot stage optical microscopy, scanning electron microscopy (SEM), electron crystallography and quantitative analysis, particle size analysis (PSA), surface area analysis, solubility, and rate of dissolution. As used herein to refer to the spectra or data presented in graphical form (e.g., XRPD, DSC, IR, Raman, and NMR spectra), and unless otherwise indicated, the term “peak” refers to a peak or other special feature that one skilled in the art would recognize as not attributable to background noise. As used herein and unless otherwise indicated, the term “substantially pure” when used to describe a solid means a solid form of the compound that comprises one or more crystalline polymorphs disclosed herein in at least 50% by weight, and in another embodiment, in at least 60% by weight, and in another embodiment, in at least 70% by weight, and in another embodiment, in at least 75% by weight, and in a further embodiment, in at least 80% by weight, and in another embodiment, in at least 85% by weight, and in another embodiment, in at least 90% by weight, and in a further embodiment, in at least 95% by weight, and in an even further embodiment, in at least 97%, or 98%, or 99%, or 100% by weight of the solid. As used herein and unless otherwise indicated, the term “polymorphically pure” when used to describe a polymorph of a compound, means a solid form of the compound that comprises that polymorph and is substantially free of other polymorphs of the compound. For example, a representative polymorphically pure solid comprises greater than 80% by weight of one polymorphic form of the compound and less than 20% by weight of other polymorphic forms of the compound, while in another embodiment, greater than 90% by weight of one polymorphic form of the compound and less than 10% by weight of other polymorphic forms of the compound, and in a still further embodiment, greater than 95% by weight of one polymorphic form of the compound and less than 5% by weight of other polymorphic forms of the compound, and in an even further embodiment, greater than 97% by weight of one polymorphic form of the compound and less than 3% by weight of other polymorphic forms of the compound. The term “enantiomerically pure” when referring to a salt or freebase herein refers to the salt or freebase being present predominantly in one enantiomer and substantially free of the other enantiomer. For example, an enantiomerically pure salt or freebase comprises greater than 80% by weight of one enantiomeric form of the salt or freebase, and less than 20% by weight of the other enantiomer of the salt or freebase, while in another embodiment, greater than 90% by weight of one enantiomer and less than 10% by weight of the other enantiomer of the salt or freebase, and in a still further embodiment, greater than 95% by weight of one enantiomer and less than 5% by weight of the other enantiomer of the salt or freebase, and in an even further embodiment, greater than 97% by weight of one enantiomer and less than 3% by weight of the other enantiomer of the salt or freebase. The term “pharmaceutically acceptable” (such as in the recitation of a pharmaceutically acceptable excipient or carrier) refers to a material that is compatible with administration to a human subject, e.g., the material does not cause an undesirable biological effect. Examples of pharmaceutically acceptable excipients are described in the “Handbook of Pharmaceutical Excipients,” Rowe et al., Ed. (Pharmaceutical Press, 7thED., 2012). The terms “treating” and “treatment” refer to ameliorating, suppressing, eradicating, reducing the severity of, decreasing the frequency of, decreasing the incidence of, reducing the risk of, slowing the progression of damage caused by, delaying the onset of the condition, or improving the quality of life of a human patient or subject suffering from a condition. The terms "effective amount" or “therapeutically effective amount” refer to an amount of a crystalline salt described herein, a pharmaceutical composition comprising the same, a medicament comprising the same, or another material comprising the same, which is effective to achieve a particular pharmacological and / or physiological effect including, but not limited to, reducing the frequency or severity of sadness or lethargy, depressed mood, anxious or sad feelings, diminished interest in all or nearly all activities, significant increased or decreased appetite leading to weight gain or weight loss, insomnia, irritability, fatigue, feelings of worthlessness, feelings of helplessness, inability to concentrate, and recurrent thoughts of death or suicide; or providing a desired pharmacologic and / or physiologic effect, for example, reducing, inhibiting, or reversing one or more of the underlying pathophysiological mechanisms underlying the neurological dysfunction, modulating dopamine levels or signaling, modulating serotonin levels or signaling, modulating norepinephrine levels or signaling, modulating glutamate or GABA levels or signaling, modulating synaptic connectivity or neurogenesis in certain brain regions, or a combination thereof. The precise dosage will vary according to a variety of factors, such as subject- dependent variables (e.g., age, immune system health, clinical symptoms, etc.), the disease or disorder being treated, as well as the route of administration and the pharmacokinetics of the agent being administered. The term “therapeutic index” used in reference to any salt disclosed herein and associated therapeutic effects and side effects refers to the ratio of the dose of said salt required to induce a particular negative side effect to the dose of said salt required to induce the desired therapeutic effect. “Patient” or “subject” refers to animals, and can include any mammal, such as humans, rats, mice, cats, dogs, goats, sheep, horses, monkeys, apes, rabbits, cattle, etc. The mammalian subject can be in any stage of development including adults, children, infants, and neonates. Unless indicated to the contrary, the terms “drugs” and “medicament” are synonymous. As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having,” or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements, but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. When referring to a solid, the term “substantially comprising crystalline” followed by reference to a compound name, such as oxanoribogaine, including the stereoisomers, salts, and polymorphs thereof, such as (-)-oxanoribogaine or (+)-oxanoribogaine hydrochloride, fumarate, phosphate, or p-toluenesulfonate, refers to a solid having at least 50 wt% of the indicated compound in the crystalline state. It may contain other impurities. For example, the compound in an amorphous state may additionally be present or another polymorph may be present, or other impurities may be present, but the sum of these impurities is not more than 50 wt%. In an embodiment, the solid may contain at least 55 wt% of the indicated compound in a crystalline state, and in another embodiment, at least 60 wt% of the indicated compound in a crystalline state, and in a further embodiment, at least 65 wt% of the indicated compound in a crystalline state, and in a still further embodiment, at least 70 wt% of the indicated compound in a crystalline state, and in a further embodiment, at least 75 wt% of the indicated compound in a crystalline state, and in a further embodiment, at least 80 wt% of the indicated compound in a crystalline state, and in a still further embodiment, at least 85 wt% of the indicated compound in a crystalline state, and in another embodiment, at least 90 wt% of the indicated compound in a crystalline state, and in a still further embodiment, at least 95 wt% of the indicated compound in a crystalline state, and in an even further embodiment, at least 99 wt% of the indicated compound in a crystalline state. Thus the amount of the indicated compound present in a crystalline state in the solid may be 50 wt%, 51 wt%, 52 wt%, 53 wt%, 54 wt%, 55 wt%, 56 wt%, 57 wt%, 58 wt%, 59 wt%, 60 wt%, 61 wt%, 62 wt%, 63 wt%, 64 wt%, 65 wt%, 66 wt%, 67 wt%, 68 wt%, 69 wt%, 70 wt%, 71 wt%, 72 wt%, 73 wt%, 74 wt%, 75 wt%, 76 wt%, 77 wt%, 78 wt%, 79 wt%, 80 wt%, 81 wt%, 82 wt%, 83 wt%, 84 wt%, 85 wt%, 86 wt%, 87 wt%, 88 wt%, 89 wt%, 90 wt%, 91 wt%, 92 wt%, 93 wt%, 94 wt%, 95 wt%, 96 wt%, 97 wt%, 98 wt%, 99 wt%, or 100 wt%. When referring to a figure or other graphical representation of data relating to any crystal, solid, polymorph, or a mixture thereof described herein, the terms “substantially”, “substantially as depicted”, and “substantially as shown” mean characterized by the graphical data in the identified figure subject to small variations, for example, variations in peak intensities or peak positions in X-ray diffraction patterns due to factors such as variation in instrumental response, aspect ratio, particle size, experimental error, and variations in sample concentration or purity. Nevertheless, one of skill in the art will readily be capable of comparing the graphical data in the figures herein with graphical data for a second polymorph, crystal, or solid form to confirm whether the two sets of graphical data are characterizing the same material or two different materials. It should be understood that all figures are thus representative of the inherent properties of the polymorph, crystal, or solid form to which they relate and that the particular data presented is substantially as depicted in the figure whether or not the modifier substantially is explicitly included in any description of said figure. The terms “substantially”, “substantially as depicted”, and “substantially as shown” in reference to a DSC thermogram, refer to the peak temperatures being about the values shown and with the same number of peaks as depicted. Also, the use of “a” or “an” are employed to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be read to include one or at least one. Moreover, the singular also includes the plural and vice versa unless it is obvious that it is meant otherwise. Further, unless expressly stated to the contrary, “or” refers to an inclusive “or” and not to an exclusive “or.” For example, a condition A or B is satisfied by any one of the following: A is true (or present), and B is false (or not present), A is false (or not present), and B is true (or present), and both A and B are true (or present). Moreover, the term “and / or” is synonymous with the term “or”, as used herein. When a range or list of values is expressed, an embodiment includes the endpoint of the ranges and / or list and all the points therebetween. For example, a range of 6 to 9, includes the value 6 and 9 and all values therebetween. Similarly, when values are expressed as approximations, by use of the antecedent “about,” it will be understood that the values range from about the two endpoints, where “about” is defined as herein described. All ranges are inclusive and combinable. Further, reference to values stated in ranges includes each and every value within that range. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present disclosure, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, unless a particular passage is cited. In case of conflict, the present specification, including definitions, will control. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting. Unless indicated to the contrary, all percentages are by weight. The term “salts disclosed herein” or “salt disclosed herein” refers to any of the salts disclosed in the exemplification, including crystalline salts. These salts are pharmaceutically acceptable salts. The present disclosure relates, in part, to a crystalline salt of oxanoribogaine, including the stereoisomers thereof, such as (-)-oxanoribogaine or (+)-oxanoribogaine, or mixtures of the stereoisomers thereof, such as rac-oxanoribogaine. These include the hydrochloride thereof, the fumarate thereof, the phosphate thereof, and the p-toluenesulfonate thereof. Some of these salts exist in various polymorphic forms, as described herein, and are included in the present disclosure. In an embodiment, the present disclosure relates to solids that are substantially a crystalline form of any of the disclosed salts of oxanoribogaine, including the stereoisomers thereof, such as (-)-oxanoribogaine or (+)-oxanoribogaine, or mixtures of the stereoisomers thereof, such as rac-oxanoribogaine. The solid may be polymorphically pure, that is, comprising only one crystalline polymorph described herein, or alternatively, it may comprise a mixture of two or more of the aforementioned crystalline polymorphs. In an embodiment, the solid contains one or more of the crystalline polymorphs with at least one crystalline polymorph described herein present in a quantity of at least 50% by weight, and in a further embodiment, in at least 55% by weight, and in a further embodiment, in at least 60% by weight, and in a further embodiment, in at least 65% by weight, and in another embodiment, in at least 70% by weight, and in a further embodiment, in at least 75% by weight, and in a further embodiment, in at least 80% by weight, and in an even further embodiment, in at least 85% by weight, and in an even further embodiment, in at least 90% by weight, and in an even further embodiment, in at least 95% by weight, and in a further embodiment, in at least 98% by weight, and in a further embodiment, in at least 99% by weight. In another embodiment, the solid comprises a mixture of polymorphs. In an embodiment, the solid is polymorphically pure. That is, it contains one crystalline polymorph substantially free of other crystalline polymorphs. In addition, regardless of whether the solid is polymorphically pure or contains a mixture, it may contain other materials, such as a pharmaceutically acceptable carrier or adjuvant(s) known in the pharmaceutical arts or optionally non-polymorphic impurities. In an embodiment, the solid may be substantially pure. In another embodiment, it may be polymorphically pure, and in a still further embodiment, it may be both substantially pure and polymorphically pure. In a further embodiment, it may be polymorphically pure and enantiomerically pure. In a further embodiment, it may be substantially pure, enantiomerically pure, and polymorphically pure. In addition, in an embodiment, the solid is anhydrous, that is, contains less than 5% by weight water. Thus, in an embodiment, the solid is anhydrous and substantially pure, and in another embodiment, is polymorphically pure and is anhydrous, and in a still further embodiment, is substantially pure, polymorphically pure, and is anhydrous. In a still further embodiment, the solid is substantially pure, enantiomerically pure, polymorphically pure, and is anhydrous. The salts of the present disclosure are prepared by reacting the free base, such as (-)- oxanoribogaine free base, with an acid to effectuate the formation of the salt. Since the reactions do not affect the chiral center of the free base, the resulting salt product maintains the stereochemistry of the free base. Examples of acids include hydrochloric acid, sulfuric acid, p-tolunesulfonic acid, methanesulfonic acid, phosphoric acid, tartaric acid, fumaric acid, citric acid, glycolic acid, maleic acid, malic acid, hippuric acid, and the like, and are illustrated in the exemplification below. The selection of the solvent system for the crystallization of a salt is based on the solubility of the free base and the acid chosen. The solvent may be a single solvent or a mixture of solvents, including mixtures containing water. The techniques that can be used for salt crystallization are known to the skilled artisan. They include, but are not limited to, melt recrystallization, melt cooling, solvent crystallization, desolvation, rapid evaporation, rapid cooling, slow cooling, vapor diffusion and sublimation. The resulting crystalline products are dried by techniques known in the art, such as air drying, oven drying, vacuum drying, or evaporation of the solvent, such as water. Polymorphs can be detected, identified, classified, and characterized using well-known techniques such as, but not limited to, melting point, differential scanning calorimetry (DSC), thermogravimetry(TGA), X-ray powder diffractometry (XRPD), single crystal X-ray diffractometry, vibrational spectroscopy, solution calorimetry, solid state nuclear magnetic resonance (NMR), infrared (IR) spectroscopy, Raman spectroscopy, hot stage optical microscopy, scanning electron microscopy (SEM), electron crystallography and quantitative analysis, particle size analysis (PSA), surface area analysis, solubility, and rate of dissolution. The salts prepared are purified by techniques known in the art, such as chromatography, including column chromatography, HPLC, recrystallization, trituration, sublimation, filtration, and the like. The following non-limiting examples are exemplary for the preparation and isolation of the various salts disclosed herein, but the teachings of the present disclosure are not so limiting. EXEMPLIFICATION The following is a list of abbreviations used in this disclosure. List of Abbreviations 1H NMR Proton Nuclear Magnetic Resonance ACN Acetonitrile DMF N,N-Dimrthylforamide DMSO Dimethyl sulfoxide DSC Differential Scanning Calorimetry EtOAc Ethyl Acetate EtOH Ethanol HPLC High Performance Liquid Chromatography MtBE Methyl tert-butyl ether RT Room Temperature (20–25 °C) SFC Supercritical Fluid Chromatography THF Tetrahydrofuran UPLC Ultra Performance Liquid Chromatography XRPD X-Ray Powder Diffraction The following is a listing of the instruments and methods discussed herein. Instruments and Methods X-Ray Powder Diffraction (XRPD) XRPD was performed using a Bruker D8 Advance equipped with LYNXEYE detector in reflection mode (i.e. Bragg-Brentano geometry). Samples were prepared on Si zero-return wafers. The parameters for XRPD methods used are listed below: Parameter Regular scan High resolution scan X-ray wavelength Cu Kα1, 1.540598 Å Cu Kα1, 1.540598 Å X-ray tube setting 40 Kv, 40 Ma 40 Kv, 40 Ma Slit condition 0.6 mm div. + 2.5° soller 0.6 mm div. + 2.5° soller Scan mode Step Step Scan range (°2θ)4–30 4–40 Step size (°2θ) 0.03 0.02 Dwell time (s / step) 0.23 0.9 Spin Yes (0.5 Hz) Yes (0.5 Hz) Proton Nuclear Magnetic Resonance NMR) 1H NMR was performed on a Bruker Avance 400 or 500 MHz spectrometers. Solids were dissolved in 0.75 mL deuterated solvent (DMSO-d6) in a 2 mL vial, transferred to an NMR tube (Wilmad 5 mm thin wall 8² 200 MHz, 506-PP-8), and analyzed according to the following parameters: Parameters – Bruker Avance 400 Instrument Bruker Avance 400 MHz Neo Nanobay spectrometer Temperature 298 K Probe Z163739_0636 (PI HR-BBO400S1-BBF / H / D-5.0-Z SP) Number of scans 64 Relaxation delay 1.0000 s Pulse width 7.7000 μs Acquisition time 3.9977 s Spectrometer frequency 400.30 MHz Nucleus1H Parameters – Bruker Avance 500 Instrument Bruker Avance 500 MHz spectrometer Temperature 300 K Probe 5 mm PABBO BB-1H / D Z-GRD Z113652 / 0159 Number of scans 64 Relaxation delay 1.000 s Pulse width 14.0000 μs Acquisition time 3.2506 s Spectrometer frequency 500.13 MHz Nucleus1H Differential Scanning Calorimetry (DSC) DSC was performed using a Mettler Toledo DSC 3+. The sample (1–5 mg) was weighed directly in a 40 µL hermetic aluminum pan with a pinhole and analyzed according to the parameters below: Parameters Method Ramp Sample size 1-2 mg Heating rate 10.0 °C / min Temperature range 30 to 300 °C Method gas N2at 60.00 Ml / min Alternatively, DSC was performed using a TA Discovery DSC. The sample (1–2 mg) was weighed directly in a 40 µL hermetic aluminum pan with a pinhole and analyzed according to the parameters below: Parameters Method Ramp Sample size1–2 mg Heating rate 10.0 °C / min Temperature range 30 to 350 °C Method gas N2 at 50.00 Ml / min Ultra Performance Liquid Chromatography (UPLC) UPLC was conducted using an Agilent 1290 Infinity LC System equipped with a VWD (Variable Wavelength Detector). Flow rate range of the instrument is 0.2–5.0 mL / min, operating pressure range is 0–1300 bar, temperature range is 5 °C above ambient to 60 °C, and wavelength range is 190–600 nm. The following parameters were used in analyses: Parameters Mobile phase A 0.1 % TFA in distilled water Mobile phase B 100 % ACN Diluent ACN:distilled water (1:1 vol.) Injection volume 1 Μl Monitoring wavelength 214 nm Column Waters Acquity UPLC HSS-T3, 2.1 × 150 mm, 1.8 μm Column temperature 35 °C Time (min) % A Flow rate (mL / min) 0.0 90 0.3 1.5 90 0.3 Gradient method 3.0 85 0.3 9.0 10 0.3 12.0 10 0.3 13.5 90 0.3 15.0 90 0.3 In the examples below, the solids are analyzed by XRPD to determine if they are crystalline and if so, by DSC to determine melting point. In characterizing the polymorphs described herein, various methods, including XRPD patterns with various peaks are depicted. The peaks observed in the figures and assignments listed herein are intended to encompass variations of ±0.5 °2θ. As such, the XRPD patterns are substantially as shown, with the peaks in the Figures herein and / or Tables herein having a variation of, for example, ±0.5 °2θ or other reasonable variation as described above. The entire list of peaks or a subset thereof can be sufficient to characterize the crystalline form or characteristics thereof by a pattern substantially similar that is identifiable by one of ordinary skill using the characterization method depicted within experimental variations. EXAMPLE 1. Preparation of (-)-oxanoribogaine hydrochloride Form A. Rac-oxanoribogaine was prepared as previously described in US Patent No. 11,840,541, the contents of which are incorporated herein by reference. This rac-noribogaine (1, 11.5 g) was separated into its enantiomers by chiral SFC [Column Name: CHIRLPAK IA (21.0 mm ID*250 mm length) 5u (001) (R); Mobile Phase: {CO2-0.1% ethanolic ammonia in IPA (80:20)}; Flow Rate: 60 mL / min; Column Temp: 30°C; Pressure: 100 bar]. The separated fractions were concentrated under reduced pressure and lyophilized to afford (+)- oxanoribogaine free base (1B, first eluting enantiomer E1, off-white solid, 3.9 g) and (-)- oxanoribogaine free base (1A, second eluting enantiomer E2, off-white solid, 3.1 g) 1B: LC-MS: 298.26 9.03 (s, 1H), 7.18 (d, J = 8.4 Hz, 1H), 6.74 (d, J = 2.4 Hz, 1H), 6.62 (dd, J = 8.4, 2.4 Hz, 1H), 3.28 - 3.25 (m, 1H), 3.13 - 3.04 (m, 3H), 2.92 - 2.90 (m, 1H), 2.83 - 2.81 (m, 1H), 2.73 (s, 1H), 2.42 - 2.36 (m, 1H).2.01 - 1.95 (m, 1H), 1.80 - 1.72 (m, 2H), 1.55 - 1.45 (m, 3H), 1.41 - 1.34 (m, 1H), 1.08 - 1.04 (m, 1H), 0.86 (t, J = 7.2 Hz, 3H). 1A: LC-MS: 298.15 9.04 (s, 1H), 7.18 (d, J = 8.4 Hz, 1H), 6.75 (d, J = 2.4 Hz, 1H), 6.63 (dd, J = 8.4, 2.4 Hz, 1H), 3.29 - 3.24 (m, 1H), 3.14 - 3.06 (m, 3H), 2.93 - 2.82 (m, 2H), 2.74 (s, 1H), 2.43 - 2.37 (m, 1H), 2.02 - 1.96 (m, 1H), 1.80 - 1.74 (m, 2H), 1.56 - 1.35 (m, 5H), 1.08 - 1.05 (m, 1H), 0.87 (t, J = 7.2 Hz, 3H). To a stirred solution of (-)-oxanoribogaine free base (1A, 3.1 g, 10.42 mmol) in DCM (35 mL) was added 4M HCl in 1,4-dioxane (5.21 mL, 20.8 mmol) dropwise at 0 °C. The reaction mixture was then stirred for 3 h at room temperature (after 1 h, a white solid precipitate formed in the initially clear reaction mixture). The reaction mixture was then concentrated under reduced pressure on a rotary evaporator at 45 °C to afford the crude HCl salt. This solid was triturated with diethyl ether (50 mL) and n-pentane (40 mL) and then filtered under nitrogen using line vacuum. The collected solid was then dissolved in ACN (10 mL) and water (50 mL) and the resulting solution was lyophilized for 12 h to afford (-)-oxanoribogaine hydrochloride as an off-white solid (1A-HCl, 3.350 g, 96%). HRMS m / z 298.20 [M+1]+;1H NMR (400 MHz, DMSO-d6): δ = 10.00 (br s, 1H), 9.24 (s, 1H), 7.28 (d, J = 8.8 Hz, 1H), 6.84 (d J = 2.4 Hz,1H), 6.72 (dd, J = 8.8, 2.4 Hz, 1H), 3.67 - 3.55 (m, 3H), 3.49 (d, J = 11.2 Hz, 1H), 3.21 - 3.17 (m, 1H), 3.07 - 2.97 (m, 2H), 2.17 - 2.10 (m, 2H), 1.97 - 1.86 (m, 2H), 1.82 - 1.72 (m, 2H), 1.60 (d, J = 11.2 Hz, 1H), 1.29 - 1.28 (m, 1H), 0.91 (t, J = 7.2 Hz, 3H). The above resulting (-)-oxanoribogaine hydrochloride was designated as Form A (also referred to interchangeably as (-)-oxanoribogaine HCl Form A, (-)-oxanoribogaine HCl-A, E2-HCl-A, 1A hydrochloride Form A, 1A HCl Form A, 1A HCl-A, or 1A-HCl-A). The diffractogram of Form A is depicted in FIG.1. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 1. Table 1. XRPD peak values for FIG 1 ((-)-oxanoribogaine HCl Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 8.62 10.25 100 14.43 6.13 80 12.79 6.91 66 13.02 6.79 37 15.19 5.83 30 14.70 6.02 29 22.22 4.00 26 11.86 7.46 25 19.19 4.62 20 8.97 9.85 19 7.19 12.28 16 25.95 3.43 15 19.53 4.54 10 26.22 3.40 10 9.39 9.41 9 17.23 5.14 7 7.68 11.50 6 21.76 4.08 6 20.17 4.40 5 26.64 3.34 5 17.99 4.93 4 25.35 3.51 4 31.82 2.81 3 As shown, in an embodiment, this (-)-oxanoribogaine hydrochloride Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 8.62, 14.43, and 12.79±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 8.62, 14.43, 12.79, 13.02, and 15.19±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 8.62, 14.43, 12.79, 13.02, 15.19, 14.70, 22.22, 11.86, 19.19, and 8.97±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 1 ±0.5 °2θ. This (-)-oxanoribogaine hydrochloride Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG.2. The DSC thermogram of this (-)-oxanoribogaine hydrochloride Form A salt exhibited several peak temperatures, with the most intense peak temperature at about 281.6 °C. EXAMPLE 2. Preparation of additional polymorphs of (-)-oxanoribogaine hydrochloride. To screen for additional polymorphs of (-)-oxanoribogaine hydrochloride, short-term slurries were carried out at two temperatures in four solvents and one mixed solvent system. Approximately 20 mg of solid (-)-oxanoribogaine hydrochloride Form A was added to a 2 mL vial, followed by a 6.3 mm stir bar. Aliquots of solvent (2–5 vol.) were added at RT. In between additions, each vial was left to stir for 5–10 min (350 rpm). After stirring for four days, a small portion of each slurry was suction filtered and sampled for XRPD analysis. The temperature was raised to 50 °C and all five slurries were left to stir. The slurries were monitored and solids that crusted or stuck to the vial were redispersed. Solvent evaporation was corrected with additional solvent. After two days, another aliquot of solid was taken by filtration to assess by XRPD. Experiments that showed differences between the RT and 50 °C wet patterns were cooled back to RT and left to stir overnight. A final aliquot of solid was taken by filtration and assessed. Solids exhibiting XRPD patterns distinct from hydrochloride Form A were dried at 50 °C under active vacuum (-29 inHg) and analyzed by XRPD again. The results are summarized below in Table 2. Table 2. XRPD results from the slurry experiments with (-)-oxanoribogaine HCl Form A. XRPD Pattern Solvent RT 50 °C RTaWet Dry Wet Wet E2-HCl-C Acetone E2-HCl-B E2-HCl-D E2-HCl-D (L.C.) EtOAc E2-HCl-C E2-HCl-C E2-HCl-C - EtOH E2-HCl-D E2-HCl-D E2-HCl-D - THF E2-HCl-D - E2-HCl-D - EtOH:water E2-HCl-D - E2-HCl-D - (95:5 vol.) Note: L.C, low-crystalline. Hyphen indicates that data were not collected due to redundancy.aSecondary room temperature experiments. Three additional polymorphs of (-)-oxanoribogaine hydrochloride were observed in the slurry experiments and were designated as Form B (also referred to interchangeably as (- )-oxanoribogaine HCl Form B, (-)-oxanoribogaine HCl-B, E2-HCl-B, 1A hydrochloride Form B, 1A HCl Form B, 1A HCl-B, or 1A-HCl-B), Form C (also referred to interchangeably as (-)-oxanoribogaine HCl Form C, (-)-oxanoribogaine HCl-C, E2-HCl-C, 1A hydrochloride Form C, 1A HCl Form C, 1A HCl-C, or 1A-HCl-C), and Form D (also referred to interchangeably as (-)-oxanoribogaine HCl Form D, (-)-oxanoribogaine HCl-D, E2-HCl-D, 1A hydrochloride Form D, 1A HCl Form D, 1A HCl-D, or 1A-HCl-D). The diffractogram of Form B is depicted in FIG.3. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 3. Table 3. XRPD peak values for FIG 3 ((-)-oxanoribogaine HCl Form B). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 17.01 5.21 100 8.67 10.2 87 20.2 4.39 83 12.49 7.08 81 13.71 6.45 54 23.71 3.75 52 8.15 10.85 41 24.57 3.62 30 7.23 12.22 27 28.91 3.09 27 12.72 6.95 17 25.11 3.54 17 24.82 3.58 15 16.63 5.33 14 17.34 5.11 13 23.48 3.79 13 19.07 4.65 10 17.96 4.94 9 26.44 3.37 9 28.31 3.15 9 27 3.3 8 29.45 3.03 6 15.19 5.83 5 16.31 5.43 5 27.61 3.23 4 22.85 3.89 3 25.99 3.43 3 26.13 3.41 3 29.71 3 3 As shown, in an embodiment, this (-)-oxanoribogaine hydrochloride Form B salt can be characterized by intense peaks in the X-Ray diffractogram at 17.01, 8.67, and 20.2±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 17.01, 8.67, 20.2, 12.49, and 13.71±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 17.01, 8.67, 20.2, 12.49, 13.71, 23.71, 8.15, 24.57, 7.23, and 28.91±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 3 ±0.5 °2θ. This (-)-oxanoribogaine hydrochloride Form B salt could not be analyzed by DSC because on drying it converted to Form C. The diffractogram of Form C is depicted in FIG.4. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 4. Table 4. XRPD peak values for FIG 4 ((-)-oxanoribogaine HCl Form C). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 19.47 4.56 100 14.25 6.21 41 11.98 7.38 38 15.77 5.62 38 20.72 4.28 32 25.42 3.5 27 17.26 5.13 17 15.06 5.88 16 29.37 3.04 16 8.52 10.38 13 6.43 13.75 12 16.18 5.47 10 23.83 3.73 10 19.2 4.62 9 20.46 4.34 9 24.23 3.67 9 24.96 3.56 5 13.27 6.67 4 18.01 4.92 4 23.11 3.85 4 28.27 3.15 4 28.69 3.11 4 35.18 2.55 4 35.9 2.5 4 28.92 3.09 3 37.96 2.37 3 As shown, in an embodiment, this (-)-oxanoribogaine hydrochloride Form C salt can be characterized by intense peaks in the X-Ray diffractogram at 19.47, 14.25, and 11.98±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 19.47, 14.25, 11.98, 15.77, and 20.72±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 19.47, 14.25, 11.98, 15.77, 20.72, 25.42, 17.26, 15.06, 29.37, and 8.52±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 4 ±0.5 °2θ. This (-)-oxanoribogaine hydrochloride Form C salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG.5. The DSC thermogram of this (-)-oxanoribogaine hydrochloride Form C salt exhibited an intense peak temperature at about 290.5 °C. The diffractogram of Form D is depicted in FIG.6. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 5. Table 5. XRPD peak values for FIG 6 ((-)-oxanoribogaine HCl Form D). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 19.48 4.55 100 14.26 6.2 44 15.78 5.61 42 25.42 3.5 31 20.72 4.28 27 11.99 7.38 25 29.38 3.04 22 15.07 5.87 17 17.28 5.13 16 29.44 3.03 12 23.85 3.73 10 24.21 3.67 10 8.53 10.35 9 19.2 4.62 9 20.44 4.34 9 16.2 5.47 7 14.88 5.95 5 24.93 3.57 5 13.33 6.64 4 28.29 3.15 4 17.11 5.18 3 27.17 3.28 3 28.71 3.11 3 28.99 3.08 3 30.24 2.95 3 32.7 2.74 3 11.66 7.58 1 As shown, in an embodiment, this (-)-oxanoribogaine hydrochloride Form D salt can be characterized by intense peaks in the X-Ray diffractogram at 19.48, 14.26, and 15.78±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 19.48, 14.26, 15.78, 25.42, and 20.72±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 19.48, 14.26, 15.78, 25.42, 20.72, 11.99, 29.38, 15.07, 17.28, and 29.44±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 5 ±0.5 °2θ. This (-)-oxanoribogaine hydrochloride Form D salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG.7. The DSC thermogram of this (-)-oxanoribogaine hydrochloride Form D salt exhibited an intense peak temperature at about 291.9 °C. EXAMPLE 3. Preparation of (-)-oxanoribogaine free base. Preparation of (-)-oxanoribogaine free base was accomplished by treating (-)- oxanoribogaine hydrochloride Form A with aqueous NaHCO3according to the procedure described below. 1. The input solid (-)-oxanoribogaine hydrochloride Form A (253.2 mg) was weighed into a 20 mL scintillation vial and a 15 mm stir bar was added. The solids were dispersed in 4.0 mL of saturated aqueous NaHCO3and set to stir. a. A non-homogeneous, cream-colored mixture was observed. 2. To the same 20 mL vial, 3.0 mL of MtBE was added. The 20 mL vial was inverted and gently shaken to ensure free base extraction and was then transferred to a 10 mL separatory funnel. Aliquots of MtBE were used to rinse the 20 mL vial and also added to the separatory funnel. The combined mixture in the separatory funnel was then left to settle for 15 min. 3. The bottom aqueous layer was removed. a. All subsequent aqueous layers were collected in the same vial. b. A clear, pale-yellow organic layer and a slightly hazy, white aqueous layer were observed. 4. The organic layer was diluted with MtBE (6 mL) and then washed with sat. aq. NaHCO3(2 × 3 mL), brine (1 × 3 mL), and lastly distilled water (2 × 3 mL). 5. The organic layer was transferred through the top of the separatory funnel into a tared 20 mL vial and was left uncapped at 50 °C to evaporate. a. An amber oil was observed. 6. The resulting amber oil was then covered with a Kimwipe and left under active vacuum (-29 inHg) at 50 °C to dry overnight. An off-white, ‘foam-like’ solid was observed after drying. The recovered solids were characterized by NMR, UPLC, and XRPD to confirm successful free base generation and to assess purity and crystallinity. The diffractogram of the resulting (-)-oxanoribogaine free base is depicted in FIG.24. This free base material was designated as (-)-oxanoribogaine free base Form A (also referred to interchangeably as (-)- oxanoribogaine free base-A, E2 free base Form A, E2 free base-A, E2-free base-A, 1A free base Form A, 1A free base-A, or 1A-free base-A). The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 6. Table 6. XRPD peak values for FIG 24 ((-)-oxanoribogaine free base). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 14.13 6.26 100 14.63 6.05 77 14.76 6 75 13.41 6.6 62 13.93 6.35 62 17.53 5.05 50 18.48 4.8 47 13.15 6.73 43 17.92 4.95 37 12.48 7.09 36 15.21 5.82 34 19.39 4.57 31 12.13 7.29 28 8.95 9.87 27 18.93 4.68 27 16.15 5.49 21 24.68 3.6 20 22.07 4.02 17 21.53 4.12 16 21.24 4.18 14 22.88 3.88 13 22.26 3.99 12 25.54 3.49 10 As shown, in an embodiment, this (-)-oxanoribogaine free base can be characterized by intense peaks in the X-Ray diffractogram at 14.13, 14.63, and 14.76 ±0.5 °2θ. In another embodiment, this free base can be characterized by peaks at 14.13, 14.63, 14.76, 13.41, and 13.93±0.5 °2θ. In another embodiment, this free base can be characterized by peaks at 14.13, 14.63, 14.76, 13.41, 13.93, 17.53, 18.48, 13.15, 17.92, and 12.48±0.5 °2θ. In another embodiment, this free base can be characterized by peaks at all of the values listed in Table 6 ±0.5 °2θ. Although some peaks were observed in the XRPD pattern of the isolated free base suggesting some degree of crystallinity, the presence of amorphous (-)-oxanoribogaine as a component of the isolated solid was not ruled out. EXAMPLE 4. Preparation of additional (-)-oxanoribogaine salts. Experiments were set up for the salt screening process in 4 mL vials containing 10 mm stir bars. A stock solution of (-)-oxanoribogaine free base was prepared in EtOH with a concentration of 67.5 mg / mL. Stock solutions of counter ions were prepared in EtOH. The counter ions, their IDs, and the corresponding pKas are listed in Table 7. An aliquot of free base was added to each vial as the aforementioned EtOH stock solution, followed by the appropriate counter ion stock solution, both in the quantities indicated in Table 8. The vials were left to stir at 40 °C for 1 h before cooling to RT, after which the vials were uncapped and left to evaporate while stirring overnight at RT in atmosphere. The vials were then placed under active vacuum (~-29 inHg) at 50 °C for 3 h to dry thoroughly. Approximately 10 volumes of one of several screening solvents (EtOAc, EtOH, EtOH:water [95:5 vol.], ACN) was added to each vial, and the samples were heated to 40 °C while stirring (350 rpm). Vials that demonstrated significant precipitation or gumming were vortexed and sonicated often to ensure thorough mixing. After 2 h, the temperature was reduced to RT and the samples were left to stir overnight. EtOH and EtOAc were chosen for the first round of solvents. If no precipitation was observed, or if a slurry yielded a pattern that was already seen, the vials were left uncapped to evaporate as before, and a second round of solvent (EtOH:water [95:5 vol.]) was added (EtOH:water [95:5 vol.]). This process was repeated with a third solvent (ACN) if no unique pattern or precipitation was observed. Resulting solids were collected by filtration and analyzed by XRPD analysis in three stages. First, XRPD analysis of the wet cake was completed for all samples where solids were observed. Unique solids were then left on XRPD plates, dried under vacuum (~-29 inHg) at 50 °C for 3 h, and then analyzed again by XRPD. Finally, solids were exposed to over 95 % RH overnight and XRPD on the resulting solids was carried out. The humid environment was generated by placing a beaker of saturated potassium sulfate in water in a sealed chamber along with the samples. All XRPD patterns were compared to counter ion XRPD patterns and known free base patterns. Any crystalline patterns observed were denoted with the counter ion number (see Table 7) followed by a letter in alphabetical order for each distinct form with the same counterion (e.g., E2-2-A = (-)-oxanoribogaine phosphate Form A). Where relevant, solids were also analyzed by NMR to determine the ratio of free base to counterion. A summary of the salt screening results is shown in Table 8. Table 7. Summary of counter ion information. Counter pKa Eq. Used Counter Ion Ion # fumaric acid 13.031.1 phosphoric acid 21.961.1 sulfuric acid 3 -3 0.55, 1.1 p-toluenesulfonic 4 -7 1.1 acid Table 8. Summary of salt screening parameters and results for (-)-oxanoribogaine (E2) free base. Amount Residual XRPD Pattern Solve API:CI of (-)- nt xanorib (w (NMR) o t. %) ogaine Counte Eq. Amount RT r io Solvent (E2) free n CI of CI 95 Dry base Wet Dry % RH After 95 % RH 25.3 11.0 mg EtOH E2-1-A E2-1-A E2-1-A - N.Q. ic ( 1.00:0.49 fumar EtOH) 25.3 acid 1.1 EtOAc E2-1-A + FA 25.3 11.0 mg 95 EtOH:5 H2O E2-1-A - - - - - 25.3 ACN E2-1-A + FA E2-2-A 25.3 phosph EtOH E2-2-A E2-2-A + E2-2- E2-2-A 1.0 B (EtOH) - oric 1. 25 µL 25.3 3 aci (4.5 M) EtOAc E2-2-A 25.3 d 95 EtOH:5 H2O E2-2-A - - - - - 25.3 ACN E2-2-A 24.3 40 µLaEtOH Solution 14.5 0.55 23.8 µas L EtOAc Oiled out - - - - - 24.3 ulfuric aci 40 µLaACN Brown gum 25.3 d 21 µLb25.3 1.1 EtOH Solution 21 µLbEtOAc Solution - - - - - 25.3p-16.3 mg EtOH E2-4-A E2-4-A E2-4-A - 0.3 (EtOH) 1.00:1.02 toluenes 25.3 ulfonic 1.1 EtOAc E2-4-A 25.3 acid 16.3 mg 95 EtOH:5 H2O E2-4-A - - - - - 25.3 ACN E2-4-A + 5.5 °2θ Note: CI = counter ion; N.Q. = not quantifiable. Hyphen indicates that data not collected. a1.125 M solution. b4.5 M solution. A single stable polymorph of (-)-oxanoribogaine fumarate was observed and was designated as Form A (also referred to interchangeably as (-)-oxanoribogaine hemifumarate Form A, (-)-oxanoribogaine hemifumarate-A, E2-1-A, 1A hemifumarate Form A, 1A hemifumarate-A, or 1A-hemifumarate-A). The diffractogram of (-)-oxanoribogaine hemifumarate Form A is depicted in FIG.8. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 9. Table 9. XRPD peak values for FIG 8 ((-)-oxanoribogaine hemifumarate Form A). d- Relative Angle (°2θ) Spacing intensity (Å) (%) 5.47 16.16 100 10.91 8.1 93 17.02 5.21 73 13.75 6.44 43 17.58 5.04 40 12.35 7.16 36 16.37 5.41 20 22.9 3.88 18 24.28 3.66 16 33.06 2.71 12 24.33 3.66 10 19.8 4.48 9 23.16 3.84 9 22.36 3.97 8 33.14 2.7 7 16.29 5.44 6 21.88 4.06 6 27.41 3.25 6 26.15 3.4 5 38.76 2.32 5 22.23 4 4 23.69 3.75 4 25.01 3.56 4 25.84 3.44 4 29.65 3.01 4 36.53 2.46 4 16.53 5.36 3 20.76 4.28 3 23.92 3.72 3 24.58 3.62 3 25.56 3.48 3 25.77 3.45 3 26.29 3.39 3 29.71 3 3 29.88 2.99 3 38.86 2.32 3 As shown, in an embodiment, this (-)-oxanoribogaine hemifumarate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 5.47, 10.91, and 17.02±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 5.47, 10.91, 17.02, 13.75, and 17.58±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 5.47, 10.91, 17.02, 13.75, 17.58, 12.35, 16.37, 22.9, 24.28, and 33.06±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 9 ±0.5 °2θ. This (-)-oxanoribogaine hemifumarate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG.9. The DSC thermogram of this (-)-oxanoribogaine hemifumarate Form A salt exhibited an intense peak temperature at about 231.8 °C. A single stable polymorph of (-)-oxanoribogaine phosphate was observed and was designated as Form A (also referred to interchangeably as (-)-oxanoribogaine phosphate-A, E2-2-A, 1A phosphate Form A, 1A phosphate-A, or 1A-phosphate-A). The diffractogram of (-)-oxanoribogaine phosphate Form A is depicted in FIG.10. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 10. Table 10. XRPD peak values for FIG 10 ((-)-oxanoribogaine phosphate Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 18.83 4.71 100 10.75 8.22 42 6.3 14.02 36 13.58 6.52 23 14.01 6.32 20 12.55 7.05 19 25.71 3.46 18 16.68 5.31 17 22.6 3.93 13 14.46 6.12 12 20.02 4.43 9 24.35 3.65 9 16.33 5.42 7 17.81 4.98 7 22.46 3.96 7 23.49 3.78 7 24.61 3.61 7 22.84 3.89 6 25.18 3.53 6 8.15 10.83 5 15.41 5.75 5 19.86 4.47 5 21.8 4.07 5 25.39 3.51 4 27.25 3.27 3 28.38 3.14 3 28.69 3.11 3 19.31 4.59 2 As shown, in an embodiment, this (-)-oxanoribogaine phosphate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 18.83, 10.75, and 6.3±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 18.83, 10.75, 6.3, 13.58, and 14.01±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 18.83, 10.75, 6.3, 13.58, 14.01, 12.55, 25.71, 16.68, 22.6, and 14.46±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 10 ±0.5 °2θ. This (-)-oxanoribogaine phosphate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG.11. The DSC thermogram of this (-)-oxanoribogaine phosphate Form A salt exhibited several peak temperatures, with the most intense peak temperature at about 231.7 °C. A single stable polymorph of (-)-oxanoribogaine p-toluenesulfonate was observed and was designated as Form A (also referred to interchangeably as (-)-oxanoribogaine p- toluenesulfonate-A, E2-4-A, 1A p-toluenesulfonate Form A, 1A p-toluenesulfonate-A, or 1A- p-toluenesulfonate-A). The diffractogram of (-)-oxanoribogaine p-toluenesulfonate Form A is depicted in FIG.12. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 11. Table 11. XRPD peak values for FIG 12 ((-)-oxanoribogaine p-toluenesulfonate Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 7.15 12.35 100 11.71 7.55 23 21.36 4.16 19 11.41 7.75 15 14.18 6.24 14 17.82 4.97 14 19.25 4.61 13 13.34 6.63 12 21.49 4.13 12 20.12 4.41 11 14.72 6.01 8 19.92 4.45 8 22.08 4.02 8 16.76 5.29 7 25.17 3.54 6 27.09 3.29 6 16.84 5.26 5 21.85 4.07 5 23.29 3.82 5 25.89 3.44 5 27.42 3.25 5 9.58 9.22 4 20.83 4.26 4 9.93 8.9 3 12.85 6.88 3 20.93 4.24 3 25.94 3.43 3 27.48 3.24 3 31.64 2.83 3 As shown, in an embodiment, this (-)-oxanoribogaine p-toluenesulfonate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 7.15, 11.71, and 21.36±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 7.15, 11.71, 21.36, 11.41, and 14.18±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 7.15, 11.71, 21.36, 11.41, 14.18, 17.82, 19.25, 13.34, 21.49, and 20.12±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 11 ±0.5 °2θ. This (-)-oxanoribogaine p-toluenesulfonate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 13. The DSC thermogram of this (-)-oxanoribogaine p-toluenesulfonate Form A salt exhibited an intense peak temperature at about 274.6 °C. No crystalline sulfate salts of (-)-oxanoribogaine were obtained under the conditions tested. EXAMPLE 5. Preparation of rac-oxanoribogaine hydrochloride Form A. Rac-oxanoribogaine was prepared as previously described in US Patent No. 11,840,541, the contents of which are incorporated herein by reference. To a stirred solution of rac-oxanoribogaine free base (1, 19.0 g, 63.89 mmol) in DCM (190 mL) was added 4M HCl in 1,4-dioxane (31.94 mL, 127.77 mmol) dropwise at 0 °C. The reaction mixture was then stirred for 2 h at room temperature (after 1 h, a white solid precipitate formed in the initially clear reaction mixture). The reaction mixture was then concentrated under reduced pressure on a rotary evaporator at 45 °C to afford the crude HCl salt. This solid was washed with diethyl ether (2 x 30 mL) and then dried again under vacuum. The resulting solid was than dissolved in ACN (30 mL) and water (100 mL) and the resulting solution was lyophilized for 12 h to afford rac-oxanoribogaine hydrochloride as an off-white solid (1-HCl, 19.10 g, 90%). HRMS m / z 298.20 [M+1]+;1H NMR (400 MHz, DMSO-d6): δ = 9.72 (br s, 1H), 9.23 (s, 1H), 7.28 (d, J=8.8 Hz, 1H), 6.832 (s, 1H), 6.72 (dd, J=2.4 Hz, 8.40 Hz, 1H), 3.65-3.55 (m, 3H), 3.50- 3.47 (m, 1H), 3.35-3.33 (m, 1H), 3.24-3.20 (m, 1H), 3.13-3.04 (m, 1H), 3.01-2.97 (m, 1H). 2.17-2.10 (m, 2H), 1.99-1.87 (m, 2H), 1.78-1.63 (m, 2H), 1.63-1.59 (m, 1H), 1.26-1.25 (m, 1H), 0.91 (t, J=7.2 Hz, 7.2 Hz, 3H). The above resulting rac-oxanoribogaine hydrochloride was designated as Form A (also referred to interchangeably as rac-oxanoribogaine HCl Form A, rac-oxanoribogaine HCl-A, Rac-HCl-A, 1 hydrochloride Form A, 1 HCl Form A, 1 HCl-A, or 1-HCl-A). The diffractogram of Form A is depicted in FIG.14. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 12. Table 12. XRPD peak values for FIG 14 (rac-oxanoribogaine HCl Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 8.66 10.2 100 14.61 6.06 79 7.31 12.09 48 11.84 7.47 48 14.45 6.13 42 9.31 9.49 36 15.34 5.77 36 12.99 6.81 26 23.95 3.71 21 22.48 3.95 20 26.13 3.41 15 26.61 3.35 13 23.48 3.79 10 19.58 4.53 9 21.98 4.04 8 24.34 3.65 7 17.34 5.11 6 20.26 4.38 6 16.61 5.33 4 14.85 5.96 3 18.66 4.75 3 19.24 4.61 3 25.71 3.46 3 As shown, in an embodiment, this rac-oxanoribogaine hydrochloride Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 8.66, 14.61, and 7.31±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 8.66, 14.61, 7.31, 11.84, and 14.45±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 8.66, 14.61, 7.31, 11.84, 14.45, 9.31, 15.34, 12.99, 23.95, and 22.48±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 12 ±0.5 °2θ. This rac-oxanoribogaine hydrochloride Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 15. The DSC thermogram of this rac-oxanoribogaine hydrochloride Form A salt exhibited an intense peak temperature at about 292.4 °C. EXAMPLE 6. Preparation of additional polymorphs of rac-oxanoribogaine hydrochloride. To screen for additional polymorphs of rac-oxanoribogaine hydrochloride, short-term slurries were carried out at two temperatures in four solvents and one mixed solvent system. Approximately 20 mg of solid rac-oxanoribogaine hydrochloride Form A was added to a 2 mL vial, followed by a 6.3 mm stir bar. Aliquots of solvent (2–5 vol.) were added at RT. In between additions, each vial was left to stir for 5–10 min (350 rpm). After stirring for four days, a small portion of each slurry was suction filtered and sampled for XRPD analysis. The temperature was raised to 50 °C and all five slurries were left to stir. The slurries were monitored and solids that crusted or stuck to the vial were redispersed. Solvent evaporation was corrected with additional solvent. After two days, another aliquot of solid was taken by filtration to assess by XRPD. Experiments that showed differences between the RT and 50 °C wet patterns were cooled back to RT and left to stir overnight. A final aliquot of solid was taken by filtration and assessed. Solids exhibiting XRPD patterns distinct from hydrochloride Form A were dried at 50 °C under active vacuum (-29 inHg) and analyzed by XRPD again. The results are summarized below in Table 13. Table 13. XRPD results from the slurry experiments with rac-oxanoribogaine HCl Form A. XRPD Pattern Solvent RT 50 °C RTaWet Dry Wet Dry Wet Dry Rac- Rac- Rac-HCl- Acetone - - - HCl-A HCl-A A Rac- Rac-HCl- EtOAc - - - - HCl-A A Rac-HCl- Rac-HCl- Rac- Rac- Rac- EtOH - A + Rac- A + Rac- HCl-A HCl-B HCl-B HCl-B HCl-B Rac- Rac-HCl- THF - - - - HCl-A A EtOH:water Rac- - - - - - (95:5 vol.) HCl-A Note: Hyphen indicates data were not collected either due to redundancy, or if a solution was observed.aSecondary room temperature experiment, from cooling the 50 °C slurry. One additional polymorph of rac-oxanoribogaine hydrochloride was observed in the slurry experiments and was designated as Form B (also referred to interchangeably as rac- oxanoribogaine HCl Form B, rac-oxanoribogaine HCl-B, Rac-HCl-B, 1 hydrochloride Form B, 1 HCl Form B, 1 HCl-B, or 1-HCl-B). The diffractogram of Form B is depicted in FIG.16. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 14. Table 14. XRPD peak values for FIG 16 (rac-oxanoribogaine HCl Form B). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 15.53 5.7 100 10.03 8.81 44 23.37 3.8 43 9.97 8.86 37 16.87 5.25 26 21.56 4.12 21 19.51 4.55 19 21.38 4.15 17 25.41 3.5 17 7.76 11.38 16 24.16 3.68 13 13.73 6.44 12 17.64 5.02 12 18.02 4.92 12 21.29 4.17 12 20.36 4.36 11 14.53 6.09 8 16.25 5.45 8 31.33 2.85 8 8.55 10.33 7 13.5 6.55 7 21.15 4.2 7 15.86 5.58 6 22.86 3.89 6 7.51 11.77 5 11.61 7.62 5 27.12 3.29 5 29.37 3.04 5 23 3.86 4 27.81 3.21 4 31.08 2.88 4 31.15 2.87 4 13.22 6.69 3 18.28 4.85 3 21.9 4.06 3 25.08 3.55 3 25.18 3.53 3 26.85 3.32 3 28.44 3.14 3 29.8 3 3 35.03 2.56 3 35.11 2.55 3 As shown, in an embodiment, this rac-oxanoribogaine hydrochloride Form B salt can be characterized by intense peaks in the X-Ray diffractogram at 15.53, 10.03, and 23.37±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 15.53, 10.03, 23.37, 9.97, and 16.87±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 15.53, 10.03, 23.37, 9.97, 16.87, 21.56, 19.51, 21.38, 25.41, and 7.76±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 14 ±0.5 °2θ. This rac-oxanoribogaine hydrochloride Form B salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 17. The DSC thermogram of this rac-oxanoribogaine hydrochloride Form B salt exhibited an intense peak temperature at about 281.9 °C. EXAMPLE 7. Preparation of rac-oxanoribogaine free base. Preparation of rac-oxanoribogaine free base was accomplished by treating rac- oxanoribogaine hydrochloride Form A with aqueous NaHCO3 according to the procedure described below. 7. The input solid rac-oxanoribogaine hydrochloride Form A (255.5 mg) was weighed into a 20 mL scintillation vial and a 15 mm stir bar was added. The solids were dispersed in 4.0 mL of sat. aq. NaHCO3 and set to stir at 200 rpm. a. A non-homogeneous, cream-colored mixture was observed. 8. To the same 20 mL vial, 3.0 mL of MtBE was added. The 20 mL vial was inverted and gently shaken to ensure free base extraction and was then transferred to a 10 mL separatory funnel. Aliquots of MtBE were used to rinse the 20 mL vial and also added to the separatory funnel. The combined mixture in the separatory funnel was then left to settle for 15 min. 9. The bottom aqueous layer was removed. a. All subsequent aqueous layers were collected in the same vial. b. A clear, pale-yellow organic layer and a slightly hazy, white aqueous layer were observed. 10. The organic layer was diluted with MtBE (6 mL) and then washed with sat. aq. NaHCO3 (2 × 3 mL), brine (1 × 3 mL), and lastly distilled water (2 × 3 mL). 11. The organic layer was transferred through the top of the separatory funnel into a tared 20 mL vial and was left uncapped at 50 °C to evaporate. a. An amber oil was observed. 12. The resulting amber oil was then covered with a Kimwipe and left under active vacuum (-29 inHg) at 50 °C to dry overnight. A pale-yellow, ‘foam-like’ solid was observed after drying. The recovered solids were characterized by NMR, UPLC, and XRPD to confirm successful free base generation and to assess purity and crystallinity. The free base prepared by this method was found to be amorphous. EXAMPLE 8. Preparation of additional rac-oxanoribogaine salts. Experiments were set up for the salt screening process in 4 mL vials containing 10 mm stir bars. A stock solution of rac-oxanoribogaine free base was prepared in EtOH with a concentration of 69.1 mg / mL. Stock solutions of counter ions were prepared in EtOH. The counter ions, their IDs, and the corresponding pKas are listed in Table 15. An aliquot of free base was added to each vial as the aforementioned EtOH stock solution, followed by the appropriate counter ion stock solution, both in the quantities indicated in Table 16. The vials were left to stir at 40 °C for 1 h before cooling to RT, after which the vials were uncapped and left to evaporate while stirring overnight at RT in atmosphere. The vials were then placed under active vacuum (~-29 inHg) at 50 °C for 3 h to dry thoroughly. Approximately 10 volumes of one of several screening solvents (EtOAc, EtOH, EtOH:water [95:5 vol.], ACN) was added to each vial, and the samples were heated to 40 °C while stirring (350 rpm). Vials that demonstrated significant precipitation or gumming were vortexed and sonicated often to ensure thorough mixing. After 2 h, the temperature was reduced to RT and the samples were left to stir overnight. EtOH and EtOAc were chosen for the first round of solvents. If no precipitation was observed, or if a slurry yielded a pattern that was already seen, the vials were left uncapped to evaporate as before, and a second round of solvent (EtOH:water [95:5 vol.]) was added (EtOH:water [95:5 vol.]). This process was repeated with a third solvent (ACN) if no unique pattern or precipitation was observed. Resulting solids were collected by filtration and analyzed by XRPD analysis in three stages. First, XRPD analysis of the wet cake was completed for all samples where solids were observed. Unique solids were then left on XRPD plates, dried under vacuum (~-29 inHg) at 50 °C for 3 h, and then analyzed again by XRPD. Finally, solids were exposed to over 95 % RH overnight and XRPD on the resulting solids was carried out. The humid environment was generated by placing a beaker of saturated potassium sulfate in water in a sealed chamber along with the samples. All XRPD patterns were compared to counter ion XRPD patterns and known free base patterns. Any crystalline patterns observed were denoted with the counter ion number (see Table 15) followed by a letter in alphabetical order for each distinct form with the same counterion (e.g., Rac-2-A = rac-oxanoribogaine phosphate Form A). Where relevant, solids were also analyzed by NMR to determine the ratio of free base to counterion. A summary of the salt screening results is shown in Table 16. Table 15. Summary of counter ion information. Counter pKa Eq. Used Counter Ion Ion # fumaric acid 1 3.03 1.1 phosphoric acid 2 1.96 1.1 sulfuric acid 3 -3 0.55, 1.1 p-toluenesulfonic 4 -7 1.1 acid Table 16. Summary of salt screening parameters and results for rac-oxanoribogaine (Rac) free base. Residual XRPD Solv API:CI Amou ent (NM t of (w R) n t. %) rac- Counter Eq. Amount Ion CI of C Solvents oxanor I 95 % ibogai Wet Dry RH ne (mg) 25.9 11.3 mg EtOH Rac-1-A Rac-1-A Rac-1-A N.Q 1 ic ( .00:0.47 Fumar EtOH) 25.9 acid 1.1 EtOAc Rac-1-A 25.9 11.4 mg 95 EtOH:5 H2O Rac-1-A - - - - 25.9 ACN Rac-1-A + FA 25.9 EtOH Rac-2-A Rac-2-A Rac-2-A 2.5 ( - Phosp EtOH) 25.9 horic 1.1 21 µL EtOA 5.9 a c Rac-2-A 2 cid (4.5 M) 95 EtOH:5 H2O Rac-2-A - - - - 25.9 ACN Rac-2-A 24.6 40.4 µLaEtOH Solution 9.2 Sulfu 0.55 14.8 µLaEtOAc Oiled out - - - - 24.6 ric acid 40.4 µLaACN Brown gum 25.9 26 µLbE 25.9 1.3 tOH Solution 26 µLbEtOAc Solution - - - - 25.9 16.5 mg EtOH Rac-4-A Rac-4-A Rac-4-A 0.7 (EtOH) 1.00:0.97 25.9 TSA 1.1 EtOAc Rac-4-A 25.9 16.3 mg 95 EtOH:5 H2O Rac-4-A - - - - 25.9 ACN Rac-4-A Note: CI, counter ion; N.Q., not quantifiable. Hyphen indicates that data was not collected due to redundancy. a1.125 M solution. b4.5 M solution. A single stable polymorph of rac-oxanoribogaine fumarate was observed and was designated as Form A (also referred to interchangeably as rac-oxanoribogaine hemifumarate Form A, rac-oxanoribogaine hemifumarate-A, Rac-1-A, 1 hemifumarate Form A, 1 hemifumarate-A, or 1-hemifumarate-A). The diffractogram of rac-oxanoribogaine hemifumarate Form A is depicted in FIG. 18. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 17. Table 17. XRPD peak values for FIG 18 (rac-oxanoribogaine hemifumarate Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 13.32 6.64 100 12.03 7.35 79 16.56 5.35 63 20.74 4.28 60 21.01 4.23 46 18.97 4.67 38 20.26 4.38 30 11.74 7.53 27 22.37 3.97 23 12.44 7.11 22 15.98 5.54 20 29.52 3.02 13 16.26 5.45 11 16.93 5.23 9 23.5 3.78 7 14.18 6.24 6 27.82 3.2 6 21.38 4.15 5 25.43 3.5 5 14.34 6.17 4 25.7 3.46 4 30.64 2.92 4 6.24 14.15 3 28.56 3.12 3 28.93 3.08 3 31.38 2.85 3 33.28 2.69 3 37.79 2.38 3 37.79 2.38 3 As shown, in an embodiment, this rac-oxanoribogaine hemifumarate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 13.32, 12.03, and 16.56±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 13.32, 12.03, 16.56, 20.74, and 21.01±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 13.32, 12.03, 16.56, 20.74, 21.01, 18.97, 20.26, 11.74, 22.37, and 12.44±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 17 ±0.5 °2θ. This rac-oxanoribogaine hemifumarate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 19. The DSC thermogram of this rac-oxanoribogaine hemifumarate Form A salt exhibited an intense peak temperature at about 248.6 °C. A single stable polymorph of rac-oxanoribogaine phosphate was observed and was designated as Form A (also referred to interchangeably as rac-oxanoribogaine phosphate-A, Rac-2-A, 1 phosphate Form A, 1 phosphate-A, or 1-phosphate-A). The diffractogram of rac-oxanoribogaine phosphate Form A is depicted in FIG.20. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 18. Table 18. XRPD peak values for FIG 20 (rac-oxanoribogaine phosphate Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 6.09 14.5 100 18.28 4.85 60 10.77 8.2 30 10.96 8.07 27 12.57 7.04 27 10.13 8.73 25 16.41 5.4 18 23.83 3.73 17 22.84 3.89 16 15.39 5.75 15 12.2 7.25 14 14.64 6.05 14 12.29 7.2 13 22.52 3.94 13 15.57 5.69 10 12.76 6.93 9 22.34 3.98 7 24.21 3.67 7 26.56 3.35 6 27.54 3.24 6 15.89 5.57 5 19.46 4.56 5 20.86 4.26 5 23.27 3.82 5 24.45 3.64 5 15.06 5.88 4 18.89 4.69 4 21.01 4.23 4 22.01 4.04 3 25.22 3.53 3 As shown, in an embodiment, this rac-oxanoribogaine phosphate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 6.09, 18.28, and 10.77±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 6.09, 18.28, 10.77, 10.96, and 12.57±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 6.09, 18.28, 10.77, 10.96, 12.57, 10.13, 16.41, 23.83, 22.84, and 15.39±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 18 ±0.5 °2θ. This rac-oxanoribogaine phosphate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 21. The DSC thermogram of this rac-oxanoribogaine phosphate Form A salt exhibited several peak temperatures, with the most intense peak temperature at about 227.6 °C. A single stable polymorph of rac-oxanoribogaine p-toluenesulfonate was observed and was designated as Form A (also referred to interchangeably as rac-oxanoribogaine p- toluenesulfonate-A, Rac-4-A, 1 p-toluenesulfonate Form A, 1 p-toluenesulfonate-A, or 1-p- toluenesulfonate-A). The diffractogram of rac-oxanoribogaine p-toluenesulfonate Form A is depicted in FIG.22. The peak values and relative intensities (compared to the most intense peak) of the XPRD are provided below in Table 19. Table 19. XRPD peak values for FIG 22 (rac-oxanoribogaine p-toluenesulfonate Form A). d- Relative Angle Spacing intensity (°2θ) (Å) (%) 12.31 7.19 100 11.16 7.93 85 18.53 4.79 64 18.2 4.87 59 24.69 3.6 46 6.17 14.31 33 20.21 4.39 21 21.7 4.09 19 21.83 4.07 16 23.75 3.74 13 22.08 4.02 12 14.45 6.12 11 13.99 6.33 10 19.12 4.64 9 12 7.37 8 11.34 7.8 6 21 4.23 6 29.08 3.07 6 30.99 2.88 5 19.75 4.49 4 27.58 3.23 4 21.47 4.14 3 28.1 3.17 3 36.77 2.44 3 As shown, in an embodiment, this rac-oxanoribogaine p-toluenesulfonate Form A salt can be characterized by intense peaks in the X-Ray diffractogram at 12.31, 11.16, and 18.53±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 12.31, 11.16, 18.53, 18.20, and 24.69±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at 12.31, 11.16, 18.53, 18.20, 24.69, 6.17, 20.21, 21.70, 21.83, and 23.75±0.5 °2θ. In another embodiment, this salt can be characterized by peaks at all of the values listed in Table 19 ±0.5 °2θ. This rac-oxanoribogaine p-toluenesulfonate Form A salt was also analyzed by DSC according to the methodology described hereinabove. The data is depicted in FIG. 23. The DSC thermogram of this rac-oxanoribogaine p-toluenesulfonate Form A salt exhibited an intense peak temperature at about 294.6 °C. No crystalline sulfate salts of rac-oxanoribogaine were obtained under the conditions tested. UTILITIES AND PHARMACEUTICAL COMPOSITIONS The salts disclosed herein are useful for treating psychiatric disorders, including substance use disorders. The utility includes those uses described in international patent application PCT / US2022 / 016757, the contents of which are incorporated herein by reference. More specifically, in another aspect, provided herein is a method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a salt disclosed herein. The salts are useful in a method for treating a psychiatric disorder in a patient in need of treatment, such method comprising administering to a subject in need thereof a therapeutically effective amount of a salt or composition comprising a salt disclosed herein. Contemplated psychiatric disorders may include Depressive Disorders, e.g., Major Depressive Disorder, Persistent Depressive Disorder, Postpartum Depression, Premenstrual Dysphoric Disorder, Seasonal Affective Disorder, Psychotic Depression, Disruptive Mood Dysregulation Disorder, Substance / Medication-Induced Depressive Disorder, and Depressive Disorder Due to Another Medical Condition. The salts described herein are useful for treating refractory depression, e.g., patients suffering from a depressive disorder that does not, and / or has not, responded to adequate courses of at least one, or at least two, other antidepressant compounds or therapeutics. As used herein "depressive disorder" encompasses refractory depression. In some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Bipolar and Related Disorders, e.g., Bipolar I Disorder, Bipolar II Disorder, Cyclothymic Disorder, Substance / Medication-Induced Bipolar and Related Disorder, and Bipolar and Related Disorders due to another medical condition. In some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Substance-Related Disorders, e.g., preventing a substance use craving, diminishing a substance use craving, and / or facilitating substance use cessation or withdrawal. Substance use disorders involve abuse of psychoactive compounds such as alcohol, caffeine, cannabis, inhalants, opioids, sedatives, hypnotics, anxiolytics, stimulants, nicotine, and tobacco. As used herein "substance" or "substances" are psychoactive compounds which can be addictive, such as alcohol, caffeine, cannabis, hallucinogens, inhalants, opioids, sedatives, hypnotics, anxiolytics, stimulants, nicotine, and tobacco. For example, the methods and compositions may be used to facilitate smoking cessation or cessation of opioid use.! In some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Anxiety Disorders, e.g., Separation Anxiety Disorder, Selective Mutism, Specific Phobia, Social Anxiety Disorder (Social Phobia), Panic Disorder, Panic Attack, Agoraphobia, Generalized Anxiety Disorder, Substance / Medication-Induced Anxiety Disorder, and Anxiety Disorder Due to Another Medical Condition. In embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Obsessive-Compulsive and Related Disorders, e.g., Obsessive-Compulsive Disorder, Body Dysmorphic Disorder, Hoarding Disorder, Trichotillomania (Hair-Pulling Disorder), Excoriation (Skin-Picking) Disorder, Substance / Medication-Induced Obsessive-Compulsive, and Related Disorder, and Obsessive- Compulsive and Related Disorder Due to Another Medical Condition. In some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Trauma- and Stressor-Related Disorders, e.g., Reactive Attachment Disorder, Disinhibited Social Engagement Disorder, Posttraumatic Stress Disorder, Acute and Stress Disorder, and Adjustment Disorders. In some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Feeding and Eating Disorders, e.g., Anorexia Nervosa, Bulimia Nervosa, Binge-Eating Disorder, Pica, Rumination Disorder, and Avoidant / Restrictive Food Intake Disorder. Further, in some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Neurocognitive Disorders, e.g., Delirium, Major Neurocognitive Disorder, Mild Neurocognitive Disorder, Major or Mild Neurocognitive Disorder Due to Alzheimer’s Disease, Major or Mild Frontotemporal Neurocognitive Disorder, Major or Mild Neurocognitive Disorder With Lewy Bodies, Major or Mild Vascular Neurocognitive Disorder, Major or Mild Neurocognitive Disorder Due to Traumatic Brain Injury, Substance / Medication- Induced Major or Mild Neurocognitive Disorder, Major or Mild Neurocognitive Disorder Due to HIV Infection, Major or Mild Neurocognitive Disorder Due to Prion Disease, Major or Mild Neurocognitive Disorder Due to Parkinson’s Disease, Major or Mild Neurocognitive Disorder Due to Huntington’s Disease, Major or Mild Neurocognitive Disorder Due to Another Medical Condition, and Major or Mild Neurocognitive Disorder Due to Multiple Etiologies. Moreover, in some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Neurodevelopmental Disorders, e.g., Autism Spectrum Disorder, Attention- Deficit / Hyperactivity Disorder, Stereotypic Movement Disorder, Tic Disorders, Tourette’s Disorder, Persistent (Chronic) Motor or Vocal Tic Disorder, and Provisional Tic Disorder. Further, in some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Personality Disorders, e.g., Borderline Personality Disorder. In addition, in some embodiments, the salts disclosed herein may be used to treat a psychiatric disorder including Sexual Dysfunctions, e.g., Delayed Ejaculation, Erectile Disorder, Female Orgasmic Disorder, Female Sexual Interest / Arousal Disorder, Genito-Pelvic Pain / Penetration Disorder, Male Hypoactive Sexual Desire Disorder, Premature (Early) Ejaculation, and Substance / Medication-Induced Sexual Dysfunction. In some embodiments the salts disclosed herein may be used to treat a psychiatric disorder including Gender Dysphoria, e.g., Gender Dysphoria. In some embodiments, the salts are orally administered. In another embodiment, the salts are administered parenterally, for example, intravenously or intramuscularly. In some embodiments, methods of using the salts disclosed herein include treating a psychiatric disorder by administering to a subject in need thereof a pharmaceutical composition including about 0.01 mg to about 400 mg of a salt disclosed herein. In some embodiments, doses may be, e.g., in the range of about 0.1 to 300 mg, 0.1 to 250 mg, 0.1 to 200 mg, 0.1 to 150 mg, 0.1 to 100 mg, 0.1 to 75 mg, 0.1 to 50 mg, 0.1 to 25 mg, 0.1 to 20 mg, 0.1 to 15 mg, 0.1 to 10 mg, 0.1 to 5 mg, 0.1 to 1 mg, 10 to 300 mg, 10 to 250 mg, 10 to 200 mg, 10 to 150 mg, 10 to 100 mg, 10 to 50 mg, 10 to 25 mg, 10 to 15 mg,, 20 to 300 mg, 20 to 250 mg, 20 to 200 mg, 20 to 150 mg, 20 to 100 mg, 20 to 50 mg, 50 to 300 mg, 50 to 250 mg, 50 to 200 mg, 50 to 150 mg, 50 to 100 mg, 100 to 300 mg, 100 to 250 mg, 100 to 200 mg, with doses of, e.g., about 0.25 mg, 0.5 mg, 0.75 mg, 1 mg, 1.25 mg, 1.5 mg, 1.75 mg, 2.0 mg, 2.5 mg, 3.0 mg, 3.5 mg, 4.0 mg, 4.5 mg, 5 mg, 10 mg, 15 mg, 20 mg, 25 mg, 30, mg, 35 mg, 40 mg, 45 mg, 50 mg, 75 mg, 100 mg, 125 mg, 150 mg, 175 mg, 200 mg, 225 mg, 250 mg, 275 mg, 300 mg, and 400 mg being examples. In some embodiments, dosages may include amounts of the salts disclosed herein in the range of about, e.g., 1 mg to 200 mg, 1 mg to 100 mg, 1 mg to 50 mg, 1 mg to 40 mg, 1 mg to 30 mg, 1 mg to 20 mg, 1 mg to 15 mg, 0.01 mg to 10 mg, 0.1 mg to 15 mg, 0.15 mg to 12.5 mg, or 0.2 mg to 10 mg, with doses of 0.1 mg, 0.2 mg, 0.3 mg, 0.4 mg, 0.5 mg, 0.6 mg, 0.7 mg, 0.8 mg, 0.9 mg, 1.5 mg, 1.0 mg, 1.75 mg, 2 mg, 2.5 mg, 2.75 mg, 3 mg, 3.5 mg, 3.75 mg, 4 mg, 4.5 mg, 4.75 mg, 5 mg, 5.5 mg, 6 mg, 6.5 mg, 7 mg, 7.5 mg, 8 mg, 8.5 mg, 9 mg, 10 mg, 11 mg, 12 mg, 15 mg, 20 mg, 25 mg, 30 mg, 35 mg, 40 mg, 45 mg, 50 mg, 60 mg, 75 mg, 80 mg, 90 mg, 100 mg, 125 mg, 150 mg, and 200 mg being specific examples of doses. Typically, dosages of a salt disclosed herein are administered once, twice, three or four times daily, every other day, every three days, once weekly, once a month, every other month, four times yearly, three times yearly, twice yearly, or yearly to a patient in need thereof. In some embodiments, the dosage is about, e.g., 1-400 mg / day, or 1-300 mg / day, or 1-250 mg / day, or 1- 200 mg / day, for example 300 mg / day, 250 mg / day, 200 mg / day, 150 mg / day, 100 mg / day, 75 mg / day, 50 mg / day, 25 mg / day, 20 mg / day, 10 mg / day, 5 mg / day, or 1 mg / day. In some embodiments, pharmaceutical compositions for parenteral administration or inhalation, e.g., a spray or mist of salt disclosed herein or a sterile solution of a salt disclosed herein, include a concentration of about 0.005 mg / mL to about 500 mg / mL. In some embodiments, the compositions include a salt disclosed herein at a concentration of, e.g., about 0.05 mg / mL to about 50 mg / mL, about 0.05 mg / mL to about 100 mg / mL, about 0.005 mg / mL to about 500 mg / mL, about 0.1 mg / mL to about 50 mg / mL, about 0.1 mg / mL to about 10 mg / mL, about 0.05 mg / mL to about 25 mg / mL, about 0.05 mg / mL to about 10 mg / mL, about 0.05 mg / mL to about 5 mg / mL, or about 0.05 mg / mL to about 1 mg / mL. In some embodiments, the composition includes a salt disclosed herein at a concentration of, e.g., about 0.05 mg / mL to about 15 mg / mL, about 0.5 mg / mL to about 10 mg / mL, about 0.25 mg / mL to about 5 mg / mL, about 0.5 mg / mL to about 7 mg / mL, about 1 mg / mL to about 10 mg / mL, about 5 mg / mL to about 10 mg / mL, about 5 mg / mL to about 15 mg / mL, about 5 mg / mL to 25 mg / mL, about 5 mg / mL to 50 mg / mL, about 10 mg / mL to 100 mg / mL, about 20 mg / mL to 200 mg / mL, or about 30 mg / mL to about 300 mg / mL. In some embodiments, the pharmaceutical compositions are formulated as a total volume of about, e.g., 10 mL, 20 mL, 25 mL, 50 mL, 100 mL, 200 mL, 250 mL, or 500 mL. Typically, dosages may be administered to a subject once, twice, three or four times daily, every other day, every three days, twice weekly, once weekly, twice monthly, once monthly, every other month, four time yearly, three times yearly, twice yearly, or yearly. In some embodiments, a salt disclosed herein is administered to a subject once in the morning, or once in the evening. In some embodiments, a salt disclosed herein is administered to a subject once in the morning, and once in the evening. In some embodiments, a salt disclosed herein is administered to a subject three times a day (e.g., at breakfast, lunch, and dinner), at a dose, e.g., of 50 mg / administration (e.g., 150 mg / day). In some embodiments, a salt disclosed herein is administered to a subject at a dose of 25 mg / day in one or more doses. In some embodiments, a salt disclosed herein is administered to a subject at a dose of 50 mg / day in one or more doses. In some embodiments, a salt disclosed herein is administered to a subject at a dose of 100 mg / day in one or more doses. In some embodiments, a salt disclosed herein is administered to a subject at a dose of 150 mg / day in one or more doses. In some embodiments, a salt disclosed herein is administered to a subject at a dose of 200 mg / day in one or more doses. In some embodiments, a salt disclosed herein is administered to a subject at a dose of 250 mg / day in one or more doses. In some embodiments, the dosage of a salt disclosed herein is 0.01-100 mg / kg, 0.5-50 mg / kg, 0.5-10 mg / kg, or 25-50 mg / kg once, twice, three times, or four times daily. For example, in some embodiments, the dosage is 0.1 mg / kg, 0.25 mg / kg, 0.5 mg / kg, 1 mg / kg, 5 mg / kg, 7.5 mg / kg, or 10 mg / kg once, twice, three times, or four times daily. In some embodiments, a subject is administered a total daily dose of 0.01 mg to 500 mg of a salt disclosed herein once, twice, three times, or four times daily. In some embodiments, the total amount administered to a subject in a 24-hour period is, e.g., 5 mg, 10 mg, 20 mg, 25 mg, 30 mg, 35 mg, 40 mg, 45 mg, 50 mg, 60 mg, 75 mg, 80 mg, 90 mg, 100 mg, 125 mg, 150 mg, 175 mg, 200 mg, 225 mg, 250 mg, 275 mg, 300 mg, 325 mg, 350 mg, 375 mg, 400 mg, 425 mg, 450 mg, 475 mg, 500 mg, 525 mg, 550 mg, 575 mg, or 600 mg. In some embodiments, the subject may be started at a low dose and the dosage is escalated. In some embodiments, the subject may be started at a high dose and the dosage is decreased. In some embodiments, a salt disclosed herein is administered to a patient under the supervision of a healthcare provider. In some embodiments, a salt disclosed herein is administered to a patient under the supervision of a healthcare provider at a clinic specializing in the delivery of psychoactive treatments. In some embodiments, a salt disclosed herein is administered to a patient under the supervision of a healthcare provider at a dose intended to induce a psychedelic experience in the subject. In some embodiments, the administration to a patient under the supervision of a healthcare provider occurs periodically in order to maintain a therapeutic effect in the patient, e.g., every three days, twice weekly, once weekly, twice monthly, once monthly, every other month, four times yearly, thrice yearly, twice yearly, or once yearly. In some embodiments, a salt disclosed herein is administered by a patient on their own at home or otherwise away from the supervision of a healthcare provider. In some embodiments, the administration by a patient on their own occurs periodically in order to maintain a therapeutic effect in the patient, e.g., daily, every other day, every three days, twice weekly, once weekly, twice monthly, or once monthly. In some embodiments, a salt disclosed herein may be administered at specified intervals. For example, during treatment a patient may be administered a salt disclosed herein at intervals of every, e.g., 1 year, 6 months, 120 days, 90 days, 60 days, 30 days, 14 days, 7 days, 3 days, 24 hours, 12 hours, 8 hours, 6 hours, 5 hours, 4 hours, 3 hours, 2.5 hours, 2.25 hours, 2 hours, 1.75 hours, 1.5 hours, 1.25 hours, 1 hour, 0.75 hour, 0.5 hour, or 0.25 hour. In some embodiments, a pharmaceutical composition comprises one or more of the salts disclosed herein. In some embodiments, a salt disclosed herein is used in any of the methods, uses, or compositions described herein. The present disclosure thus also relates to pharmaceutical compositions comprising a salt disclosed herein in admixture with pharmaceutically acceptable auxiliaries, and optionally other therapeutic agents. The auxiliaries must be “acceptable” in the sense of being compatible with the other ingredients of the composition and not deleterious to the recipients thereof. Pharmaceutical compositions include those suitable for oral, rectal, nasal, topical (including transdermal, buccal, and sublingual), vaginal, or parenteral (including subcutaneous, intramuscular, intravenous, and intradermal) administration or administration via an implant. The compositions may be prepared by any method well known in the art of pharmacy. Such methods include the step of bringing in association a salt disclosed herein with any auxiliary agent. The auxiliary agent(s), also include accessory ingredient(s), include those conventional in the art, such as carriers, fillers, binders, diluents, disintegrants, lubricants, colorants, flavoring agents, anti-oxidants, and wetting agents. Such auxiliary agents are suitably selected with respect to the intended form and route of administration and as consistent with conventional pharmaceutical practices. Pharmaceutical compositions suitable for oral administration may be presented as discrete dosage units such as pills, tablets, dragées or capsules, or as a powder or granules, or as a solution or suspension. The active ingredient comprised of a salt disclosed herein may also be presented as a bolus or paste. The compositions can further be processed into a suppository or enema for rectal administration. Tablets may contain as the active ingredient, a salt disclosed in association with suitable binders, lubricants, disintegrating agents, coloring agents, flavoring agents, flow-inducing agents, and melting agents. Gelatin capsules may contain the active ingredient salt disclosed herein and powdered carriers, such as lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. Similar diluents can be used to make compressed tablets. Compressed tablets can be sugar coated or film coated to mask any unpleasant taste and protect the tablet from the atmosphere, or enteric coated for selective disintegration in the gastrointestinal tract. For instance, for oral administration in the dosage unit form of a tablet or capsule, the active drug component comprised of a salt disclosed herein can be combined with an oral, non-toxic, pharmaceutically acceptable, inert carrier such as lactose, gelatin, agar, starch, sucrose, glucose, methyl cellulose, magnesium stearate, dicalcium phosphate, calcium sulfate, mannitol, sorbitol, and the like. Suitable binders include starch, gelatin, natural sugars such as glucose or beta- lactose, corn sweeteners, natural and synthetic gums such as acacia, tragacanth, or sodium alginate, carboxymethylcellulose, polyethylene glycol, waxes, and the like. Lubricants used in these dosage forms include sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, sodium chloride, and the like. Disintegrators include, without limitation, starch, methyl cellulose, agar, bentonite, xanthan gum, and the like. For oral administration in liquid dosage form, one or more salts disclosed herein, are combined with any oral, non-toxic, pharmaceutically acceptable inert carrier such as ethanol, glycerol, water, and the like. Examples of suitable liquid dosage forms include solutions or suspensions in water, pharmaceutically acceptable fats and oils, alcohols, or other organic solvents, including esters, emulsions, syrups or elixirs, suspensions, solutions and / or suspensions reconstituted from non-effervescent granules and effervescent preparations reconstituted from effervescent granules. Such liquid dosage forms may contain, for example, suitable solvents, preservatives, emulsifying agents, suspending agents, diluents, sweeteners, thickeners, and melting agents. Liquid dosage forms for oral administration can contain coloring and flavoring to increase patient acceptance. For parenteral administration, suitable compositions include aqueous and non-aqueous sterile solutions comprised of one or more salts disclosed herein. In general, water, a suitable oil, saline, aqueous dextrose (glucose), and related sugar solutions and glycols such as propylene glycol or polyethylene glycols are suitable carriers for parenteral solutions. Solutions for parenteral administration preferably contain a water-soluble salt of the active ingredient, i.e., a salt disclosed herein, and suitable stabilizing agents, and if necessary, buffer substances. Antioxidizing agents such as sodium bisulfite, sodium sulfite, or ascorbic acid, either alone or combined, are suitable stabilizing agents. Also used are citric acid and its salts and sodium EDTA. In addition, parenteral solutions can contain preservatives, such as benzalkonium chloride, methyl- or propyl-paraben, and chlorobutanol. The compositions may be presented in unit-dose or multi-dose containers, for example sealed vials and ampoules, and may be stored in a freeze-dried (lyophilized) condition requiring only the addition of sterile liquid carrier, for example water, prior to use. For transdermal administration, e.g., gels, patches or sprays can be contemplated. Compositions or formulations suitable for pulmonary administration e.g., by nasal inhalation, include fine dusts or mists which may be generated by means of metered dose pressurized aerosols, nebulizers, or insufflators. Parenteral and intravenous forms may also include minerals and other materials to make them compatible with the type of injection or delivery system chosen. The salts disclosed herein used in the method of the present disclosure may also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles, and multilamellar vesicles. Liposomes can be formed from a variety of phospholipids, such as cholesterol, stearylamine, or phosphatidylcholines. The salts disclosed herein may be administered as components of tissue-targeted emulsions. The salts disclosed herein used in the method of the present disclosure may also be coupled to soluble polymers as targetable drug carriers or as prodrugs. Such polymers include polyvinylpyrrolidone, pyran copolymer, polyhydroxylpropylmethacrylamide-phenol, polyhydroxyethylaspartamide-phenol, or polyethyleneoxide-polylysine substituted with palmitoyl residues. Furthermore, the salts disclosed herein may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example, polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacylates, and crosslinked or amphipathic block copolymers of hydrogels. Pharmaceutical compositions herein may be provided with immediate release, delayed release, extended release, or modified release profiles. In some embodiments, pharmaceutical compositions with different drug release profiles may be combined to create a two-phase or three-phase release profile. For example, pharmaceutical compositions may be provided with an immediate release and an extended-release profile. Such composition may be provided as pulsatile formulations, multilayer tablets, or capsules containing tablets, beads, granules, etc. Pharmaceutical compositions herein may be provided with abuse deterrent features by techniques known in the art, for example, by making a tablet that is difficult to crush or to dissolve in water. The pharmaceutical composition, as hereinbefore described, may be in combination with packaging material, including instructions for the use of the composition for a use as hereinbefore described. The exact dose and regimen of administration of the composition comprised of salts disclosed herein, will necessarily be dependent upon the type and magnitude of the therapeutic or nutritional effect to be achieved and may vary depending on factors such as the particular compound, formula, route of administration, or age and condition of the individual subject to whom the composition is to be administered. Furthermore, in some embodiments, a pharmaceutical composition disclosed herein may include a single enantiomer, diastereomer, or structural isomer of a salt disclosed herein, where such stereoisomers exist. In other embodiments, a pharmaceutical composition disclosed herein may include a mixture of at least one single enantiomer, diastereomer, or structural isomer of a salt disclosed herein. together with another enantiomer, diastereomer or structural isomer of a salt disclosed herein. In further embodiments, said mixture is a racemic mixture. In other embodiments, said mixture is a non-racemic mixture (wherein one enantiomer or diastereomer is enriched in said non-racemic mixture). In some embodiments, the salts disclosed herein are substantially pure, or are enantiomerically pure, or both, or may contain polymorphs of any of the salts disclosed herein. The salts disclosed herein may be administered in various forms, including those detailed herein. The treatment with the salt disclosed may be a component of a combination therapy or an adjunct therapy, i.e., the subject or patient in need of the drug is treated or given another drug for the disease in conjunction with one or more of the instant salts. This combination therapy can be sequential therapy where the patient is treated first with one drug and then the other or the two drugs can be given simultaneously. These can be administered independently by the same route or by two or more different routes of administration depending on the dosage forms employed. While certain features of the invention have been illustrated and described herein, many modifications, substitutions, changes, and equivalents will now occur to those of ordinary skill in the art. It is, therefore, to be understood that the appended claims are intended to cover all such modifications and changes as fall within the true spirit of the invention.

Claims

WHAT IS CLAIMED IS:

1. A crystalline salt of (-)-oxanoribogaine comprising crystalline (-)-oxanoribogaine hydrochloride, crystalline (-)-oxanoribogaine fumarate, crystalline (-)-oxanoribogaine phosphate, or crystalline (-)-oxanoribogaine p-toluenesulfonate.

2. The crystalline salt of claim 1, which is crystalline (-)-oxanoribogaine hydrochloride.

3. The crystalline salt of claim 2, which is crystalline (-)-oxanoribogaine hydrochloride Form A.

4. The crystalline salt of claim 3 characterized by an X-ray powder diffraction pattern comprising peaks at 8.62, 14.43, and 12.79±0.5 °2θ.

5. The crystalline salt of claim 3 characterized by an X-ray powder diffraction pattern comprising peaks at 8.62, 14.43, 12.79, 13.02, and 15.19±0.5 °2θ.

6. The crystalline salt of claim 3 characterized by an X-ray powder diffraction pattern comprising peaks at 8.62, 14.43, 12.79, 13.02, 15.19, 14.70, 22.22, 11.86, 19.19, and 8.97±0.5 °2θ.

7. The crystalline salt of claim 3 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 8.62 14.43 12.79 13.02 15.19 14.70 22.22 11.86 19.19 8.97 7.19 25.95 19.53 26.22 9.39 17.23 7.68 21.7620.17 26.64 17.99 25.35 31.82 8. The crystalline salt of claim 3 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

1.

9. The crystalline salt of any one of claims 3-8 characterized by a DSC thermogram having at least one endotherm with a peak at about 281.6 °C.

10. The crystalline salt of any one of claims 3-9 characterized by a DSC thermogram substantially as depicted in FIG.

2.

11. The crystalline salt of claim 2 which is crystalline (-)-oxanoribogaine hydrochloride Form B.

12. The crystalline salt of claim 11 characterized by an X-ray powder diffraction pattern comprising peaks at 17.01, 8.67, and 20.2±0.5 °2θ.

13. The crystalline salt of claim 11 characterized by an X-ray powder diffraction pattern comprising peaks at 17.01, 8.67, 20.2, 12.49, and 13.71±0.5 °2θ.

14. The crystalline salt of claim 11 characterized by an X-ray powder diffraction pattern comprising peaks at 17.01, 8.67, 20.2, 12.49, 13.71, 23.71, 8.15, 24.57, 7.23, and 28.91±0.5 °2θ.

15. The crystalline salt of claim 11 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 17.01 8.67 20.2 12.49 13.71 23.71 8.15 24.57 7.23 28.91 12.7225.11 24.82 16.63 17.34 23.48 19.07 17.96 26.44 28.31 27 29.45 15.19 16.31 27.61 22.85 25.99 26.13 29.71 16. The crystalline salt of claim 11 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

3.

17. The crystalline salt of claim 2 which is crystalline (-)-oxanoribogaine hydrochloride Form C.

18. The crystalline salt of claim 17 characterized by an X-ray powder diffraction pattern comprising peaks at 19.47, 14.25, and 11.98±0.5 °2θ.

19. The crystalline salt of claim 17 characterized by an X-ray powder diffraction pattern comprising peaks at 19.47, 14.25, 11.98, 15.77, and 20.72±0.5 °2θ.

20. The crystalline salt of claim 17 characterized by an X-ray powder diffraction pattern comprising peaks at 19.47, 14.25, 11.98, 15.77, 20.72, 25.42, 17.26, 15.06, 29.37, and 8.52±0.5 °2θ.

21. The crystalline salt of claim 17 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 19.47 14.25 11.9815.77 20.72 25.42 17.26 15.06 29.37 8.52 6.43 16.18 23.83 19.2 20.46 24.23 24.96 13.27 18.01 23.11 28.27 28.69 35.18 35.9 28.92 37.96 22. The crystalline salt of claim 17 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

4.

23. The crystalline salt of any one of claims 17-22 characterized by a DSC thermogram having at least one endotherm with a peak at about 290.5 °C.

24. The crystalline salt of any one of claims 17-23 characterized by a DSC thermogram substantially as depicted in FIG.

5.

25. The crystalline salt of claim 2 which is crystalline (-)-oxanoribogaine hydrochloride Form D.

26. The crystalline salt of claim 25 characterized by an X-ray powder diffraction pattern comprising peaks at 19.48, 14.26, and 15.78±0.5 °2θ.

27. The crystalline salt of claim 25 characterized by an X-ray powder diffraction pattern comprising peaks at 19.48, 14.26, 15.78, 25.42, and 20.72±0.5 °2θ.

28. The crystalline salt of claim 25 characterized by an X-ray powder diffraction pattern comprising peaks at 19.48, 14.26, 15.78, 25.42, 20.72, 11.99, 29.38, 15.07, 17.28, and 29.44±0.5 °2θ.

29. The crystalline salt of claim 25 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 19.48 14.26 15.78 25.42 20.72 11.99 29.38 15.07 17.28 29.44 23.85 24.21 8.53 19.2 20.44 16.2 14.88 24.93 13.33 28.29 17.11 27.17 28.71 28.99 30.24 32.7 11.66 30. The crystalline salt of claim 25 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

6.

31. The crystalline salt of any one of claims 25-30 characterized by a DSC thermogram having at least one endotherm with a peak at about 291.9 °C.

32. The crystalline salt of any one of claims 25-31 characterized by a DSC thermogram substantially as depicted in FIG.

7.

33. The crystalline salt of claim 1 which is crystalline (-)-oxanoribogaine fumarate.

34. The crystalline salt of claim 33 which is crystalline (-)-oxanoribogaine hemifumarate.

35. The crystalline salt of claim 34 which is crystalline (-)-oxanoribogaine hemifumarate Form A.

36. The crystalline salt of claim 35 characterized by an X-ray powder diffraction pattern comprising peaks at 5.47, 10.91, and 17.02±0.5 °2θ.

37. The crystalline salt of claim 35 characterized by an X-ray powder diffraction pattern comprising peaks at 5.47, 10.91, 17.02, 13.75, and 17.58±0.5 °2θ.

38. The crystalline salt of claim 35 characterized by an X-ray powder diffraction pattern comprising peaks at 5.47, 10.91, 17.02, 13.75, 17.58, 12.35, 16.37, 22.9, 24.28, and 33.06±0.5 °2θ.

39. The crystalline salt of claim 35 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 5.47 10.91 17.02 13.75 17.58 12.35 16.37 22.9 24.28 33.06 24.33 19.8 23.16 22.36 33.14 16.29 21.88 27.41 26.1538.76 22.23 23.69 25.01 25.84 29.65 36.53 16.53 20.76 23.92 24.58 25.56 25.77 26.29 29.71 29.88 38.86 40. The crystalline salt of claim 35 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

8.

41. The crystalline salt of any one of claims 35-40 characterized by a DSC thermogram having at least one endotherm with a peak at about 231.8 °C.

42. The crystalline salt of any one of claims 35-41 characterized by a DSC thermogram substantially as depicted in FIG.

9.

43. The crystalline salt of claim 1 which is crystalline (-)-oxanoribogaine phosphate.

44. The crystalline salt of claim 43 which is crystalline (-)-oxanoribogaine phosphate Form A.

45. The crystalline salt of claim 44 characterized by an X-ray powder diffraction pattern comprising peaks at 18.83, 10.75, and 6.3±0.5 °2θ.

46. The crystalline salt of claim 44 characterized by an X-ray powder diffraction pattern comprising peaks at 18.83, 10.75, 6.3, 13.58, and 14.01±0.5 °2θ.

47. The crystalline salt of claim 44 characterized by an X-ray powder diffraction pattern comprising peaks at 18.83, 10.75, 6.3, 13.58, 14.01, 12.55, 25.71, 16.68, 22.6, and 14.46±0.5 °2θ.

48. The crystalline salt of claim 44 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 18.83 10.75 6.3 13.58 14.01 12.55 25.71 16.68 22.6 14.46 20.02 24.35 16.33 17.81 22.46 23.49 24.61 22.84 25.18 8.15 15.41 19.86 21.8 25.39 27.25 28.38 28.69 19.31 49. The crystalline salt of claim 44 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

10.

50. The crystalline salt of any one of claims 44-49 characterized by a DSC thermogram having at least one endotherm with a peak at about 231.7 °C.

51. The crystalline salt of any one of claims 44-50 characterized by a DSC thermogram substantially as depicted in FIG.11.

52. The crystalline salt of claim 1 which is crystalline (-)-oxanoribogaine p- toluenesulfonate.

53. The crystalline salt of claim 52 which is crystalline (-)-oxanoribogaine p- toluenesulfonate Form A.

54. The crystalline salt of claim 53 characterized by an X-ray powder diffraction pattern comprising peaks at 7.15, 11.71, and 21.36±0.5 °2θ.

55. The crystalline salt of claim 53 characterized by an X-ray powder diffraction pattern comprising peaks at 7.15, 11.71, 21.36, 11.41, and 14.18±0.5 °2θ.

56. The crystalline salt of claim 53 characterized by an X-ray powder diffraction pattern comprising peaks at 7.15, 11.71, 21.36, 11.41, 14.18, 17.82, 19.25, 13.34, 21.49, and 20.12±0.5 °2θ.

57. The crystalline salt of claim 53 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 7.15 11.71 21.36 11.41 14.18 17.82 19.25 13.34 21.49 20.12 14.72 19.92 22.08 16.76 25.17 27.09 16.84 21.85 23.29 25.89 27.42 9.5820.83 9.93 12.85 20.93 25.94 27.48 31.64 58. The crystalline salt of claim 53 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

12.

59. The crystalline salt of any one of claims 53-58 characterized by a DSC thermogram having at least one endotherm with a peak at about 274.6 °C.

60. The crystalline salt of any one of claims 53-60 characterized by a DSC thermogram substantially as depicted in FIG.

13.

61. A solid comprising one or more of the crystalline salts of (-)-oxanoribogaine of claims 1-60.

62. The solid of claim 61 comprising at least 50% by weight of any one of the crystalline salts of (-)-oxanoribogaine.

63. The solid of claim 61 comprising at least 90% by weight of any one of the crystalline salts of (-)-oxanoribogaine.

64. The solid of claim 61 comprising at least 95% by weight of any one of the crystalline salts of (-)-oxanoribogaine.

65. The solid of claim 61 comprising at least 97% by weight of any one of the crystalline salts of (-)-oxanoribogaine.

66. The solid of claim 61 comprising a mixture of two or more of the crystalline salts of (- )-oxanoribogaine.

67. A solid comprising a substantially chemically and polymorphically pure form of any one of the crystalline salts of (-)-oxanoribogaine of any one of claims 1-60.

68. A pharmaceutical composition comprising one or more of the crystalline salts of (-)- oxanoribogaine of any one of claims 1-60.

69. A method of treating a psychiatric disorder comprising administering a therapeutically effective amount of one or more of the crystalline salts of (-)-oxanoribogaine of any one of claims 1-60.

70. A crystalline salt of rac-oxanoribogaine comprising crystalline rac-oxanoribogaine hydrochloride, crystalline rac-oxanoribogaine fumarate, crystalline rac- oxanoribogaine phosphate, or crystalline rac-oxanoribogaine p-toluenesulfonate.

71. The crystalline salt of claim 70, which is crystalline rac-oxanoribogaine hydrochloride.

72. The crystalline salt of claim 71, which is crystalline rac-oxanoribogaine hydrochloride Form A.

73. The crystalline salt of claim 72 characterized by an X-ray powder diffraction pattern comprising peaks at 8.66, 14.61, and 7.31±0.5 °2θ.

74. The crystalline salt of claim 72 characterized by an X-ray powder diffraction pattern comprising peaks at 8.66, 14.61, 7.31, 11.84, and 14.45±0.5 °2θ.

75. The crystalline salt of claim 72 characterized by an X-ray powder diffraction pattern comprising peaks at 8.66, 14.61, 7.31, 11.84, 14.45, 9.31, 15.34, 12.99, 23.95, and 22.48±0.5 °2θ.

76. The crystalline salt of claim 72 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 8.66 14.61 7.31 11.84 14.45 9.31 15.34 12.99 23.95 22.48 26.13 26.61 23.4819.58 21.98 24.34 17.34 20.26 16.61 14.85 18.66 19.24 25.71 77. The crystalline salt of claim 72 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

14.

78. The crystalline salt of any one of claims 72-77 characterized by a DSC thermogram having at least one endotherm with a peak at about 292.4 °C.

79. The crystalline salt of any one of claims 72-78 characterized by a DSC thermogram substantially as depicted in FIG.

15.

80. The crystalline salt of claim 71, which is crystalline rac-oxanoribogaine hydrochloride Form B.

81. The crystalline salt of claim 80 characterized by an X-ray powder diffraction pattern comprising peaks at 15.53, 10.03, and 23.37±0.5 °2θ.

82. The crystalline salt of claim 80 characterized by an X-ray powder diffraction pattern comprising peaks at 15.53, 10.03, 23.37, 9.97, and 16.87±0.5 °2θ.

83. The crystalline salt of claim 80 characterized by an X-ray powder diffraction pattern comprising peaks at 15.53, 10.03, 23.37, 9.97, 16.87, 21.56, 19.51, 21.38, 25.41, and 7.76±0.5 °2θ.

84. The crystalline salt of claim 80 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 15.53 10.03 23.37 9.9716.87 21.56 19.51 21.38 25.41 7.76 24.16 13.73 17.64 18.02 21.29 20.36 14.53 16.25 31.33 8.55 13.5 21.15 15.86 22.86 7.51 11.61 27.12 29.37 23 27.81 31.08 31.15 13.22 18.28 21.9 25.08 25.18 26.85 28.44 29.8 35.03 35.11 85. The crystalline salt of claim 80 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

16.

86. The crystalline salt of any one of claims 80-85 characterized by a DSC thermogram having at least one endotherm with a peak at about 281.9 °C.

87. The crystalline salt of any one of claims 80-86 characterized by a DSC thermogram substantially as depicted in FIG.

17.

88. The crystalline salt of claim 70, which is crystalline rac-oxanoribogaine fumarate.

89. The crystalline salt of claim 88, which is crystalline rac-oxanoribogaine hemifumarate.

90. The crystalline salt of claim 89, which is crystalline rac-oxanoribogaine hemifumarate Form A.

91. The crystalline salt of claim 90 characterized by an X-ray powder diffraction pattern comprising peaks at 13.32, 12.03, and 16.56±0.5 °2θ.

92. The crystalline salt of claim 90 characterized by an X-ray powder diffraction pattern comprising peaks at 13.32, 12.03, 16.56, 20.74, and 21.01±0.5 °2θ.

93. The crystalline salt of claim 90 characterized by an X-ray powder diffraction pattern comprising peaks at 13.32, 12.03, 16.56, 20.74, 21.01, 18.97, 20.26, 11.74, 22.37, and 12.44±0.5 °2θ.

94. The crystalline salt of claim 90 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 13.32 12.03 16.56 20.74 21.01 18.97 20.26 11.74 22.37 12.44 15.98 29.52 16.26 16.93 23.5 14.18 27.82 21.3825.43 14.34 25.7 30.64 6.24 28.56 28.93 31.38 33.28 37.79 37.79 95. The crystalline salt of claim 90 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

18.

96. The crystalline salt of any one of claims 90-95 characterized by a DSC thermogram having at least one endotherm with a peak at about 248.6 °C.

97. The crystalline salt of any one of claims 90-96 characterized by a DSC thermogram substantially as depicted in FIG.

19.

98. The crystalline salt of claim 70, which is crystalline rac-oxanoribogaine phosphate.

99. The crystalline salt of claim 98, which is crystalline rac-oxanoribogaine phosphate Form A.

100. The crystalline salt of claim 99 characterized by an X-ray powder diffraction pattern comprising peaks at 6.09, 18.28, and 10.77±0.5 °2θ.

101. The crystalline salt of claim 99 characterized by an X-ray powder diffraction pattern comprising peaks at 6.09, 18.28, 10.77, 10.96, and 12.57±0.5 °2θ.

102. The crystalline salt of claim 99 characterized by an X-ray powder diffraction pattern comprising peaks at 6.09, 18.28, 10.77, 10.96, 12.57, 10.13, 16.41, 23.83, 22.84, and 15.39±0.5 °2θ.

103. The crystalline salt of claim 99 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 6.0918.28 10.77 10.96 12.57 10.13 16.41 23.83 22.84 15.39 12.2 14.64 12.29 22.52 15.57 12.76 22.34 24.21 26.56 27.54 15.89 19.46 20.86 23.27 24.45 15.06 18.89 21.01 22.01 25.22 104. The crystalline salt of claim 99 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

20.

105. The crystalline salt of any one of claims 99-104 characterized by a DSC thermogram having at least one endotherm with a peak at about 227.6 °C.

106. The crystalline salt of any one of claims 99-105 characterized by a DSC thermogram substantially as depicted in FIG.

21.

107. The crystalline salt of claim 70, which is crystalline rac-oxanoribogaine p- toluenesulfonate.

108. The crystalline salt of claim 107, which is crystalline rac-oxanoribogaine p- toluenesulfonate Form A.

109. The crystalline salt of claim 108 characterized by an X-ray powder diffraction pattern comprising peaks at 12.31, 11.16, and 18.53±0.5 °2θ.

110. The crystalline salt of claim 108 characterized by an X-ray powder diffraction pattern comprising peaks at 12.31, 11.16, 18.53, 18.20, and 24.69±0.5 °2θ.

111. The crystalline salt of claim 108 characterized by an X-ray powder diffraction pattern comprising peaks at 12.31, 11.16, 18.53, 18.20, 24.69, 6.17, 20.21, 21.70, 21.83, and 23.75±0.5 °2θ.

112. The crystalline salt of claim 108 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (±0.5 °2θ) 12.31 11.16 18.53 18.2 24.69 6.17 20.21 21.7 21.83 23.75 22.08 14.45 13.99 19.12 12 11.34 21 29.08 30.99 19.75 27.58 21.47 28.1 36.77 113. The crystalline salt of claim 108 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.22.

114. The crystalline salt of any one of claims 108-113 characterized by a DSC thermogram having at least one endotherm with a peak at about 294.6 °C.

115. The crystalline salt of any one of claims 108-114 characterized by a DSC thermogram substantially as depicted in FIG.

23.

116. A solid comprising one or more of the crystalline salts of rac-oxanoribogaine of claims 70-115.

117. The solid of claim 116 comprising at least 50% by weight of any one of the crystalline salts of rac-oxanoribogaine.

118. The solid of claim 116 comprising at least 90% by weight of any one of the crystalline salts of rac-oxanoribogaine.

119. The solid of claim 116 comprising at least 95% by weight of any one of the crystalline salts of rac-oxanoribogaine.

120. The solid of claim 116 comprising at least 97% by weight of any one of the crystalline salts of rac-oxanoribogaine.

121. The solid of claim 116 comprising a mixture of two or more of the crystalline salts of rac-oxanoribogaine.

122. A solid comprising a substantially chemically and polymorphically pure form of any one of the crystalline salts of rac-oxanoribogaine of any one of claims 70-115.

123. A pharmaceutical composition comprising one or more of the crystalline salts of rac-oxanoribogaine of any one of claims 70-115.

124. A method of treating a psychiatric disorder comprising administering a therapeutically effective amount of one or more of the crystalline salts of rac- oxanoribogaine of any one of claims 70-115.

125. Crystalline (-)-oxanoribogaine free base.

126. The crystalline free base of claim 125, which is crystalline (-)-oxanoribogaine free base Form A.

127. The crystalline free base of claim 126 characterized by an X-ray powder diffraction pattern comprising peaks at 14.13, 14.63, and 14.76 ±0.5 °2θ.

128. The crystalline free base of claim 126 characterized by an X-ray powder diffraction pattern comprising peaks at 14.13, 14.63, 14.76, 13.41, and 13.93±0.5 °2θ.

129. The crystalline free base of claim 126 characterized by an X-ray powder diffraction pattern comprising peaks at 14.13, 14.63, 14.76, 13.41, 13.93, 17.53, 18.48, 13.15, 17.92, and 12.48±0.5 °2θ.

130. The crystalline free base of claim 126 characterized by an X-ray powder diffraction pattern comprising peaks at: Angle (°2θ) 14.13 14.63 14.76 13.41 13.93 17.53 18.48 13.15 17.92 12.48 15.21 19.39 12.13 8.95 18.93 16.15 24.68 22.07 21.53 21.24 22.88 22.26 25.54 131. The crystalline free base of claim 126 characterized by an X-ray powder diffraction pattern substantially as depicted in FIG.

24.

132. A solid comprising the crystalline (-)-oxanoribogaine free base of any one of claims 125-131.

133. The solid of claim 132 comprising at least 50% by weight of the crystalline (- )-oxanoribogaine free base.

134. The solid of claim 132 comprising at least 90% by weight of the crystalline (- )-oxanoribogaine free base.

135. The solid of claim 132 comprising at least 95% by weight of the crystalline (- )-oxanoribogaine free base.

136. The solid of claim 132 comprising at least 97% by weight of the crystalline (- )-oxanoribogaine free base.

137. A solid comprising a substantially chemically and polymorphically pure form of the crystalline (-)-oxanoribogaine free base of any one of claims 125-131.

138. A pharmaceutical composition comprising the crystalline (-)-oxanoribogaine free base of any one of claims 125-131.

139. A method of treating a psychiatric disorder comprising administering a therapeutically effective amount of the crystalline (-)-oxanoribogaine free base of any one of claims 125-131.

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