Fluorinated cannabinoid compositions and methods thereof

Abstract

The present disclosure relates to certain fluorinated compounds, pharmaceutical compositions containing them, and methods of making and using them.

Description

[0001] Attorney Docket No.91392-415912 FLUORINATED CANNABINOID COMPOSITIONS AND METHODS THEREOF CROSS-REFERENCE TO RELATED APPLICATIONS This application claims the benefit of U.S. Provisional Application Serial No.63 / 546,842, filed November 1, 2023, and U.S. Provisional Application Serial No.63 / 634,677, filed April 16, 2024, the disclosures of which are incorporated herein by reference in their entireties. TECHNICAL FIELD The present disclosure relates to certain fluorinated compounds, pharmaceutical compositions containing them, and methods of making and using them. BACKGROUND Cannabis compounds such as cannabinoids offer a wide range of therapeutic benefits. For instance, cannabinoids have applications in pain, spasticity associated with multiple sclerosis, nausea, posttraumatic stress disorder, cancer, epilepsy, cachexia, glaucoma, HIV / AIDS, and degenerative neurological illnesses. However, most cannabinoids including cannabidiol (CBD) have a complicated pharmacokinetic profile due to their high lipophilicity, poor solubility, and first-pass metabolism. All these characteristics contribute to a low bioavailability, the low rate at which a chemical is absorbed by the bloodstream. Tetrahydrocannabinol (THC) and CBD have been extensively studied as they occur in greater amounts in the cannabis plant, whereas cannabinol (CBN) must be converted from CBD or THC. However, there are distinct advantages of CBN compared to CBD, for instance enhanced bioavailability. Therefore, there exists a need to develop cannabinoids, particularly CBN derivatives, that provides benefits such as enhanced bioavailability. SUMMARY The present disclosure provides synthetic methods to carry out structural changes in cannabis derivatives, or cannabinoids, with the aim of providing cannabinoid compositions with enhanced bioavailability. Generally, the present disclosure provides cannabinoid derivatives and the synthetic methods of fluorinating cannabinoids to provide fluorinated cannabinoid compositions. In particular, fluorinated cannabinoids are of interests for medical applications in treating a variety of diseases. As detailed in the present disclosure, several advantages can be realized using the described fluorination methods and fluorinated compositions of cannabinoids. First, the present disclosure describes fluorination methods as they can provide improvement in biological characteristics. Fluorination of compounds can provide enhanced pharmacokinetic and Attorney Docket No.91392-415912 physicochemical characteristics, and therefore, can in turn increase the bioavailability of the resulting compound. Furthermore, the described method of making the novel fluorinated cannabinoids is less energy- and time-consuming compared to traditional pathways. Accordingly, a lower energy input and time may be advantageous in providing higher yields and novel cannabinoid compositions. In one aspect, the disclosure provides a compound of formula A: , or a pharmaceutically R7, R8, R9, RA, RB, ring A, o, and m is defined herein. In another aspect, the disclosure provides a compound of formula A-I: I), or a pharmaceutically R7, R8, R9, R10,B R , and m is defined herein. In another aspect, the disclosure provides a compound of formula A-II:

[0002] Attorney Docket No.91392-415912 , or a pharmaceutically R8, R9, RB, and m is defined herein. In another aspect, the disclosure provides a compound of formula A-III: m In another aspect, the disclosure provides a compound of formula I: , or a pharmaceutically R4, R5, R6, R7, R8, and R9is defined herein. In another aspect, the disclosure provides a compound of formula II: Attorney Docket No.91392-415912 R5, or a pharmaceutically R3, R4, R5, R6, R7, 89 R , and R is defined In another aspect, the disclosure provides a compound of formula III: , or a pharmaceutically R3a, R4, R5, R6 7 , R , R8, and R9is defined herein. In another aspect, the disclosure provides a compound of formula IV: , or a pharmaceutically Attorney Docket No.91392-415912 In another aspect, the disclosure provides a compound of formula V: , or a pharmaceutically herein. In another , or a pharmaceutically herein. In another aspect, the disclosure provides a compound of formula VII: , or a pharmaceutically acceptable R4, R5, R6, R7, R8, R9, and R10is defined herein. In another aspect, the disclosure provides a compound of formula VIII: Attorney Docket No.91392-415912 , or a pharmaceutically In another aspect, the comprising at least a compound of the disclosure, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or vehicles. In another aspect, the disclosure provides a method of treating a disease in a patient comprising administering to the patient in need of such treatment an effective amount of a compound of the disclosure, or a pharmaceutically acceptable salt thereof. In yet another aspect, the disclosure provides a method of preparing a compound of the disclosure, or a pharmaceutically acceptable salt thereof, comprising contacting a precursor compound with a fluorinating agent to provide the compound. DETAILED DESCRIPTION Before the present disclosure is further described, it is to be understood that this disclosure is not limited to particular embodiments described, as such may, of course, vary. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to be limiting, since the scope of the present disclosure will be limited only by the appended claims. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as is commonly understood by one of ordinary skill in the art to which this disclosure belongs. All patents, applications, published applications and other publications referred to herein are incorporated by reference in their entireties. If a definition set forth in this section is contrary to or otherwise inconsistent with a definition set forth in a patent, application, or other publication that is herein incorporated by reference, the definition set forth in this section prevails over the definition incorporated herein by reference. As used herein and in the appended claims, the singular forms “a,” “an,” and “the” include plural referents unless the context clearly dictates otherwise. It is further noted that the claims may be drafted to exclude any optional element. As such, this statement is intended to serve as antecedent basis for use of such exclusive terminology as “solely,” “only” and the like in connection with the recitation of claim elements, or use of a “negative” limitation. Attorney Docket No.91392-415912 As used herein, the terms “including,” “containing,” and “comprising” are used in their open, non-limiting sense. To provide a more concise description, some of the quantitative expressions given herein are not qualified with the term “about.” It is understood that, whether the term “about” is used explicitly or not, every quantity given herein is meant to refer to the actual given value, and it is also meant to refer to the approximation to such given value that would reasonably be inferred based on the ordinary skill in the art, including equivalents and approximations due to the experimental and / or measurement conditions for such given value. Whenever a yield is given as a percentage, such yield refers to a mass of the entity for which the yield is given with respect to the maximum amount of the same entity that could be obtained under the particular stoichiometric conditions. Concentrations that are given as percentages refer to mass ratios, unless indicated differently. Except as otherwise noted, the methods and techniques of the present embodiments are generally performed according to conventional methods well known in the art and as described in various general and more specific references that are cited and discussed throughout the present specification. See, e.g., Loudon, Organic Chemistry, Fourth Edition, New York: Oxford University Press, 2002, pp. 360-361, 1084-1085; Smith and March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, Fifth Edition, Wiley-Interscience, 2001. Chemical nomenclature for compounds described herein has generally been derived using the commercially-available ACD / Name 2014 (ACD / Labs) or ChemBioDraw Ultra 13.0 (Perkin Elmer). It is appreciated that certain features of the disclosure, which are, for clarity, described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the disclosure, which are, for brevity, described in the context of a single embodiment, may also be provided separately or in any suitable subcombination. All combinations of the embodiments pertaining to the chemical groups represented by the variables are specifically embraced by the present disclosure and are disclosed herein just as if each and every combination was individually and explicitly disclosed, to the extent that such combinations embrace compounds that are stable compounds (i.e., compounds that can be isolated, characterized, and tested for biological activity). In addition, all subcombinations of the chemical groups listed in the embodiments describing such variables are also specifically embraced by the present disclosure and are disclosed herein just as if each and every such sub-combination of chemical groups was individually and explicitly disclosed herein. Attorney Docket No.91392-415912 DEFINITIONS As used herein, the term “alkyl” includes a chain of carbon atoms, which is optionally branched and contains from 1 to 20 carbon atoms. It is to be further understood that in certain embodiments, alkyl may be advantageously of limited length, including C1-C12, C1-C10, C1-C9, C1-C8, C2-C8, C1-C7, C1-C6, C2-C6, and C1-C4, Illustratively, such particularly limited length alkyl groups, including C1-C8, C1-C6, and C1-C4, and the like may be referred to as “lower alkyl.” Illustrative alkyl groups include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, 2-pentyl, 3-pentyl, neopentyl, hexyl, heptyl, octyl, and the like. Alkyl may be substituted or unsubstituted. Typical substituent groups include cycloalkyl, aryl, heteroaryl, heteroalicyclic, hydroxy, alkoxy, aryloxy, mercapto, alkylthio, arylthio, cyano, halogen, carbonyl, oxo (=O), thiocarbonyl, O-carbamyl, N-carbamyl, O-thiocarbamyl, N- thiocarbamyl, C-amido, N-amido, C-carboxy, O-carboxy, -NO2, and amino, or as described in the various embodiments provided herein. It will be understood that “alkyl” may be combined with other groups, such as those provided above, to form a functionalized alkyl. By way of example, the combination of an “alkyl” group, as described herein, with a “halo” group may be referred to as a “haloalkyl” group. Other non-limiting examples include hydroxyalkyl, aminoalkyl, and the like. Representative examples of alkyl groups, such as those optionally substituted with halo include, but are not limited to, methyl, fluoromethyl, difluoromethyl, trifluoromethyl, and the like. As used herein, the term “alkenyl” includes a chain of carbon atoms, which is optionally branched, and contains from 2 to 20 carbon atoms, and also includes at least one carbon-carbon double bond (i.e., C=C). It will be understood that in certain embodiments, alkenyl may be advantageously of limited length, including C2-C12, C2-C10, C2-C8, C2-C7, C2-C6, and C2-C4. Illustratively, such particularly limited length alkenyl groups, including C2-C8, C2-C7, C2-C6, and C2-C4 may be referred to as lower alkenyl. Alkenyl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. Illustrative alkenyl groups include, but are not limited to, ethenyl, 1-propenyl, 2-propenyl, 1-, 2-, or 3-butenyl, and the like. As used herein, the term “alkynyl” includes a chain of carbon atoms, which is optionally branched, and contains from 2 to 20 carbon atoms, and also includes at least one carbon-carbon triple bond (i.e., C≡C). It will be understood that in certain embodiments, alkynyl may each be advantageously of limited length, including C2-C12, C2-C10, C2-C8, C2-C7, C2-C6, and C2-C4. Illustratively, such particularly limited length alkynyl groups, including C2-C8, C2-C7, C2-C6, and C2-C4may be referred to as lower alkynyl. Alkynyl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. Illustrative Attorney Docket No.91392-415912 alkynyl groups include, but are not limited to, ethynyl, 1-propynyl, 2-propynyl, 1-, 2-, or 3-butynyl, and the like. As used herein, the term “aryl” refers to an all-carbon monocyclic or fused-ring polycyclic groups of 6 to 12 carbon atoms having a completely conjugated pi-electron system. It will be understood that in certain embodiments, aryl may be advantageously of limited size such as C6- C10aryl. Illustrative aryl groups include, but are not limited to, phenyl, naphthylenyl and anthracenyl. The aryl group may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. As used herein, the term “cycloalkyl” refers to a 3 to 15 member all-carbon monocyclic ring, including an all-carbon 5-member / 6-member or 6-member / 6-member fused bicyclic ring, or a multicyclic fused ring (a “fused” ring system means that each ring in the system shares an adjacent pair of carbon atoms with each other ring in the system) group, or a carbocyclic ring that is fused to another group such as a heterocyclic, such as ring 5- or 6-membered cycloalkyl fused to a 5- to 7- membered heterocyclic ring. As used herein, the term “cycloalkenyl” refers to a cycloalkyl where one or more of the rings contains one or more double bonds but does not contain a completely conjugated pi-electron system. It will be understood that in certain embodiments, cycloalkyl or cycloalkenyl may be advantageously of limited size such as C3-C12, C3-C9, C3-C8, C3-C6 and C4-C6. Cycloalkyl or cycloalkenyl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. For example, a cycloalkyl or a cycloalkenyl may be optionally substituted with an oxo. Illustrative cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like. Illustrative cycloalkenyl groups include, but are not limited to, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, norbornenyl, and the like. Illustrative examples of cycloalkyl and cycloalkenyl groups shown in graphical representations include the following entities, in the form of properly bonded moieties: , , Attorney Docket No.91392-415912 In certain embodiments, a cycloalkenyl may be represented by the structure: . refers to a or group at least one ring atom is a heteroatom, such as nitrogen, oxygen or sulfur, the remaining ring atoms being carbon atoms. Heterocycloalkyl may optionally contain 1, 2, 3 or 4 heteroatoms. A heterocycloalkyl group may be fused to another group such as another heterocycloalkyl, an aryl, or a heteroaryl group. Heterocycloalkyl may also have one of more double bonds, including double bonds to nitrogen (e.g., C=N or N=N) but does not contain a completely conjugated pi- electron system. It will be understood that in certain embodiments, heterocycloalkyl may be advantageously of limited size such as 3- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl, 3-, 4-, 5- or 6-membered heterocycloalkyl, and the like. Heterocycloalkyl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. Illustrative heterocycloalkyl groups include, but are not limited to, oxiranyl, thianaryl, azetidinyl, oxetanyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, piperidinyl, 1,4-dioxanyl, morpholinyl, 1,4-dithianyl, piperazinyl, oxepanyl, 3,4-dihydro-2H-pyranyl, 5,6-dihydro-2H-pyranyl, 2H-pyranyl, 1, 2, 3, 4-tetrahydropyridinyl, and the like. Illustrative examples of heterocycloalkyl groups shown in graphical representations include the following entities, in the form of properly bonded moieties: H H H H O , Attorney Docket No.91392-415912 to 10 ring atoms, and also having a completely conjugated pi-electron system. It will be understood that in certain embodiments, aryl may be advantageously of limited size such as 6- to 10-membered aryl and the like. Aryl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. Illustrative aryl groups include, but are not limited to, phenyl and naphthyl. As used herein, the term “heteroaryl” refers to a monocyclic or fused ring group of 5 to 10 ring atoms containing one, two, three or four ring heteroatoms selected from nitrogen, oxygen and sulfur, the remaining ring atoms being carbon atoms, and also having a completely conjugated pi-electron system. It will be understood that in certain embodiments, heteroaryl may be advantageously of limited size such as 3- to 7-membered heteroaryl, 5- to 7-membered heteroaryl, 5- to 10-membered heteroaryl and the like. Heteroaryl may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. In some embodiments, it will be understood that an atom exo to the heteroaryl ring atoms, such as an amino or a hydroxyl group, may contribute to the pi-electron system. For example, tautomeric hydroxyl-pyridine contains an -OH group, wherein the exo oxygen contributes to the pi-electron system, illustrated in the tautomeric 2-pyridone configuration. Illustrative heteroaryl groups include, but are not limited to, pyrrolyl, furanyl, thiophenyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, purinyl, tetrazolyl, triazinyl, pyrazinyl, tetrazinyl, quinazolinyl, quinoxalinyl, thienyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, benzisoxazolyl, benzisothiazolyl and carbazoloyl, and the like. Illustrative examples of heteroaryl groups shown in graphical representations, include the following entities, in the form of properly bonded moieties: H H N , Attorney Docket No.91392-415912 NNN N N N N S O , As used herein, “alkoxy” refers to both an -O-(alkyl) or an -O-(unsubstituted cycloalkyl) group. Alkoxy may be unsubstituted, or substituted as described for alkyl or as described in the various embodiments provided herein. Representative examples include, but are not limited to, methoxy, ethoxy, propoxy, butoxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, and the like. By way of example, the combination of an “alkoxy” group, as described herein, with a “halo” group may be referred to as a “haloalkoxy” group. Representative examples of alkoxy groups, such as those substituted with halo include, but are not limited to, fluoromethoxy, difluoromethoxy, trifluoromethoxy, and the like. The term “amide”, as used herein, refers to a group and R10each independently represent a hydrogen or hydrocarbyl group, or R9and R10taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure. The terms “amine” and “amino” are art-recognized and refer to both unsubstituted and substituted amines and salts thereof, e.g., a moiety that can be represented by Attorney Docket No.91392-415912 wherein R9, R10, and R10, each independently represent a hydrogen or a hydrocarbyl group, or R9and R10taken together with the N atom to which they are attached complete a heterocycle having from 4 to 8 atoms in the ring structure. As used herein, “halo” or “halogen” refers to fluorine, chlorine, bromine or iodine. As used herein, “cyano” refers to a -CN group. The term “oxo” represents a carbonyl oxygen. For example, a cyclohexyl including an oxo is cyclohexanone. As used herein, “bond” refers to a covalent bond. The term “carboxy”, as used herein, refers to a group represented by the formula —CO2H. The term “ester”, as used herein, refers to a group —C(O)OR8wherein R8represents a hydrocarbyl group (e.g., alkyl, aryl, heteroaryl). The term “ketone”, as used herein, refers to a group —C(O)R7wherein R7represents a hydrocarbyl group (e.g., alkyl, aryl, heteroaryl). The term “ether”, as used herein, refers to a hydrocarbyl group linked through an oxygen to another hydrocarbyl group. Accordingly, an ether substituent of a hydrocarbyl group may be hydrocarbyl-O—. Ethers may be either symmetrical or unsymmetrical. Examples of ethers include, but are not limited to, heterocycle-O-heterocycle and aryl-O-heterocycle. Ethers include “alkoxyalkyl” groups, which may be represented by the general formula alkyl-O-alkyl. The term “sulfate” is art-recognized and refers to the group —OSO3H, or a pharmaceutically acceptable salt thereof. The term “sulfonamide” is art-recognized and refers to the group represented by the general formulae represents hydrogen or hydrocarbyl (e.g., alkyl, aryl, heteroaryl). The term “sulfoxide” is art-recognized and refers to the group —S(O)—. The term “sulfonate” is art-recognized and refers to the group SO3H or —OS(O)2—, or a pharmaceutically acceptable salt thereof. For example, a sulfonate may be represented by the structure -OS(O)2-alkyl or -OS(O)2-haloalkyl. Representative examples include, but are not limited to, -OS(O)2-CH3, -OS(O)2-CFH2, -OS(O)2-CF2H, -OS(O)2-CF3, and the like. The term “sulfone” is art-recognized and refers to the group —S(O)2—. For example, a sulfone may be represented by the structure -S(O)2-alkyl or -S(O)2-haloalkyl. Representative Attorney Docket No.91392-415912 examples include, but are not limited to, -S(O)2-CH3, -S(O)2-CFH2, -S(O)2-CF2H, -S(O)2-CF3, and the like. The term “hydrocarbyl”, as used herein, refers to a group that is bonded through a carbon atom that does not have a ═O or ═S substituent, and typically has at least one carbon-hydrogen bond and a primarily carbon backbone, but may optionally include heteroatoms. Thus, groups like methyl, ethoxyethyl, 2-pyridyl, and even trifluoromethyl are considered to be hydrocarbyl for the purposes of this application, but substituents such as acetyl (which has a ═O substituent on the linking carbon) and ethoxy (which is linked through oxygen, not carbon) are not. Hydrocarbyl groups include, but are not limited to aryl, hetaryl, carbocycle, heterocycle, alkyl, alkenyl, alkynyl, and combinations thereof. The term “substituted” means that the specified group or moiety bears one or more substituents. The term “unsubstituted” means that the specified group bears no substituents. Where the term “substituted” is used to describe a structural system, the substitution is meant to occur at any valency-allowed position on the system. In some embodiments, “substituted” means that the specified group or moiety bears one or more substituents. It will be understood that in certain embodiments, substitutions may be advantageously limited in number. In some embodiments, “substituted” means that the specified group or moiety bears one to five substituents. In other embodiments, “substituted” means that the specified group or moiety bears one, two, or three substituents. In other embodiments, “substituted” means that the specified group or moiety bears one or two substituents. In still other embodiments, “substituted” means the specified group or moiety bears one substituent. As used herein, the terms “optional” or “optionally” mean that the subsequently described event or circumstance may occur or may not occur, and that the description includes instances where the event or circumstance occurs as well as instances in which it does not. For example, “optionally substituted alkyl” refers to the alkyl may be substituted as well as where the alkyl is not substituted. It is understood that substituents and substitution patterns on the compounds of the present disclosure can be selected by one of ordinary skilled person in the art to result chemically stable compounds which can be readily synthesized by techniques known in the art, as well as those methods set forth below, from readily available starting materials. If a substituent is itself substituted with more than one group, it is understood that these multiple groups may be on the same carbon or on different carbons, so long as a stable structure results. As used herein, the term “optionally substituted” refers to the replacement of one to six hydrogen radicals in a given structure with the radical of a specified substituent including, but not limited to: hydroxyl, hydroxyalkyl, alkoxy, halogen, alkyl, nitro, silyl, acyl, acyloxy, aryl, Attorney Docket No.91392-415912 cycloalkyl, heterocyclyl, amino, aminoalkyl, cyano, haloalkyl, haloalkoxy, —OCO—CH2—O- alkyl, —OP(O)(O-alkyl)2 or —CH2—OP(O)(O-alkyl)2. Preferably, “optionally substituted” refers to the replacement of one to four hydrogen radicals in a given structure with the substituents mentioned above. More preferably, one to three hydrogen radicals are replaced by the substituents as mentioned above. It is understood that the substituent can be further substituted. As used herein, “independently” means that the subsequently described event or circumstance is to be read on its own relative to other similar events or circumstances. For example, in a circumstance where several equivalent hydrogen groups are optionally substituted by another group described in the circumstance, the use of “independently optionally” means that each instance of a hydrogen atom on the group may be substituted by another group, where the groups replacing each of the hydrogen atoms may be the same or different. Or for example, where multiple groups exist all of which can be selected from a set of possibilities, the use of “independently” means that each of the groups can be selected from the set of possibilities separate from any other group, and the groups selected in the circumstance may be the same or different. The term “modulate” as used herein includes the inhibition or suppression of a function or activity (such as cell proliferation) as well as the enhancement of a function or activity. The phrase “pharmaceutically acceptable” is art-recognized. In certain embodiments, the term includes compositions, excipients, adjuvants, polymers and other materials and / or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with a reasonable benefit / risk ratio. “Pharmaceutically acceptable salt” or “salt” is used herein to refer to an acid addition salt or a basic addition salt which is suitable for or compatible with the treatment of patients. The term “pharmaceutically acceptable acid addition salt” as used herein means any non- toxic organic or inorganic salt of any base compounds represented by Formula I. Illustrative inorganic acids which form suitable salts include hydrochloric, hydrobromic, sulfuric and phosphoric acids, as well as metal salts such as sodium monohydrogen orthophosphate and potassium hydrogen sulfate. Illustrative organic acids that form suitable salts include mono-, di- , and tricarboxylic acids such as glycolic, lactic, pyruvic, malonic, succinic, glutaric, fumaric, malic, tartaric, citric, ascorbic, maleic, benzoic, phenylacetic, cinnamic and salicylic acids, as well as sulfonic acids such as p-toluene sulfonic and methanesulfonic acids. Either the mono or di-acid salts can be formed, and such salts may exist in either a hydrated, solvated or substantially anhydrous form. In general, the acid addition salts of compounds of Formula I are more soluble in water and various hydrophilic organic solvents, and generally demonstrate higher melting Attorney Docket No.91392-415912 points in comparison to their free base forms. The selection of the appropriate salt will be known to one skilled in the art. Other non-pharmaceutically acceptable salts, e.g., oxalates, may be used, for example, in the isolation of compounds of Formula I for laboratory use, or for subsequent conversion to a pharmaceutically acceptable acid addition salt. The term “pharmaceutically acceptable basic addition salt” as used herein means any non- toxic organic or inorganic base addition salt of any acid compounds represented by Formula I or any of their intermediates. Illustrative inorganic bases which form suitable salts include lithium, sodium, potassium, calcium, magnesium, or barium hydroxide. Illustrative organic bases which form suitable salts include aliphatic, alicyclic, or aromatic organic amines such as methylamine, trimethylamine and picoline or ammonia. The selection of the appropriate salt will be known to a person skilled in the art. Many of the compounds useful in the methods and compositions of this disclosure have at least one stereogenic center in their structure. This stereogenic center may be present in a R or a S configuration, said R and S notation is used in correspondence with the rules described in Pure Appl. Chem. (1976), 45, 11-30. The disclosure contemplates all stereoisomeric forms such as enantiomeric and diastereoisomeric forms of the compounds, salts, prodrugs or mixtures thereof (including all possible mixtures of stereoisomers). See, e.g., WO 01 / 062726. Some of the compounds may also exist in tautomeric forms. Such forms, although not explicitly indicated in the formulae described herein, are intended to be included within the scope of the present disclosure. “Prodrug” or “pharmaceutically acceptable prodrug” refers to a compound that is metabolized, for example hydrolyzed or oxidized, in the host after administration to form the compound of the present disclosure (e.g., compounds of formula I). Typical examples of prodrugs include compounds that have biologically labile or cleavable (protecting) groups on a functional moiety of the active compound. Prodrugs include compounds that can be oxidized, reduced, aminated, deaminated, hydroxylated, dehydroxylated, hydrolyzed, dehydrolyzed, alkylated, dealkylated, acylated, deacylated, phosphorylated, or dephosphorylated to produce the active compound. Examples of prodrugs using ester or phosphoramidate as biologically labile or cleavable (protecting) groups are disclosed in U.S. Pat. Nos. 6,875,751, 7,585,851, and 7,964,580, the disclosures of which are incorporated herein by reference. The prodrugs of this disclosure are metabolized to produce a compound of Formula I. The present disclosure includes within its scope, prodrugs of the compounds described herein. Conventional procedures for the selection and preparation of suitable prodrugs are described, for example, in “Design of Prodrugs” Ed. H. Bundgaard, Elsevier, 1985. Attorney Docket No.91392-415912 The phrase “pharmaceutically acceptable carrier” as used herein means a pharmaceutically acceptable material, composition or vehicle, such as a liquid or solid filter, diluent, excipient, solvent or encapsulating material useful for formulating a drug for medicinal or therapeutic use. The term “Log of solubility”, “LogS” or “logS” as used herein is used in the art to quantify the aqueous solubility of a compound. The aqueous solubility of a compound significantly affects its absorption and distribution characteristics. A low solubility often goes along with a poor absorption. LogS value is a unit stripped logarithm (base 10) of the solubility measured in mol / liter. Any formula depicted herein is intended to represent a compound of that structural formula as well as certain variations or forms. For example, a formula given herein is intended to include a racemic form, or one or more enantiomeric, diastereomeric, or geometric isomers, or a mixture thereof. Additionally, any formula given herein is intended to refer also to a hydrate, solvate, or polymorph of such a compound, or a mixture thereof. For example, it will be appreciated that compounds depicted by a structural formula containing the symbol “ ” include both stereoisomers for the carbon atom to which the symbol “ ” specifically both the bonds “ ” and “ ” are encompassed by the meaning of “ ”. Unless otherwise the compounds as described herein, whether by chemical name or chemical structure, include all stereoisomers (e.g., enantiomers and diastereomers), double bond isomers (e.g., (Z) and (E)), conformational isomers, and tautomers of the compounds identified by the chemical names and chemical structures provided herein. In addition, single stereoisomers, double bond isomers, conformational isomers, and tautomers as well as mixtures of stereoisomers, double bond isomers, conformational isomers, and tautomers are within the scope of the disclosure. As used herein, the prefix “rac-,” when used in connection with a chiral compound, refers to a racemic mixture of the compound. As used herein, the prefix “rel-,” when used in connection with a chiral compound, refers to a single enantiomer of unknown absolute configuration. In a compound bearing the “rel-” prefix, the (R)- and (S)- designators in the chemical name reflect the relative stereochemistry of the compound, but do not necessarily reflect the absolute stereochemistry of the compound. Where the relative stereochemistry of a given stereocenter is unknown, no stereochemical designator is provided. Any formula given herein is also intended to represent unlabeled forms as well as isotopically labeled forms of the compounds. Isotopically labeled compounds have structures depicted by the formulas given herein except that one or more atoms are replaced by an atom Attorney Docket No.91392-415912 having a selected atomic mass or mass number. Examples of isotopes that can be incorporated into compounds of the disclosure include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorous, fluorine, chlorine, and iodine, such as2H,3H,11C,13C,14C,15N,18O,17O,31P,32P,35S,18F,36Cl, and125I, respectively. Such isotopically labelled compounds are useful in metabolic studies (preferably with14C), reaction kinetic studies (with, for example2H or3H), detection or imaging techniques [such as positron emission tomography (PET) or single-photon emission computed tomography (SPECT)] including drug or substrate tissue distribution assays, or in radioactive treatment of patients. For example, isotope-labeled compounds and salts can be used as medicaments. Further, substitution with heavier isotopes such as deuterium (i.e.,2H) may afford certain therapeutic advantages resulting from greater metabolic stability, for example increased in vivo half-life or reduced dosage requirements. For example, deuterium (2H)-labeled compounds and salts may be therapeutically useful with potential therapeutic advantages over the non-2H-labeled compounds. Isotopically labeled compounds of this disclosure and prodrugs thereof can generally be prepared by carrying out the procedures disclosed in the schemes or in the examples and preparations described below by substituting a readily available isotopically labeled reagent for a non-isotopically labeled reagent. Any disubstituent referred to herein is meant to encompass the various attachment possibilities when more than one of such possibilities are allowed. For example, reference to disubstituent –A-B-, where A ≠ B, refers herein to such disubstituent with A attached to a first substituted member and B attached to a second substituted member, and it also refers to such disubstituent with A attached to the second substituted member and B attached to the first substituted member. REPRESENTATIVE EMBODIMENTS In some embodiments, the disclosure relates to a compound of formula A: , or a ring A is aryl or cycloalkenyl, Attorney Docket No.91392-415912 RAis hydroxyl, alkoxy, haloalkoxy, ester, or sulfonate, wherein each alkoxy, haloalkoxy, ester, or sulfonate is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; each RBis independently halogen, alkyl, or haloalkyl; each of R4, R5, R6, and R7is independently H, halogen, alkyl, or haloalkyl; each of R8and R9is independently halogen, alkyl, or haloalkyl; each of Ra, Rb, and Rcis independently H, alkyl, or haloalkyl; o is 0 or 1; and m is 1, 2, 3, 4, or 5; provided that the compound comprises at least one fluoro. In some embodiments, the disclosure relates to a compound of formula A: , or a ring A is aryl or cycloalkenyl, RAis hydroxyl, alkoxy, haloalkoxy, ester, or sulfonate, wherein each alkoxy, haloalkoxy, ester, or sulfonate is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; each RBis independently halogen, alkyl, or haloalkyl; each of R4, R5, R6, R7, R8, and R9is independently H, halogen, alkyl, or haloalkyl; each of Ra, Rb, and Rcis independently H, alkyl, or haloalkyl; o is 0 or 1; and m is 1, 2, 3, 4, or 5; provided that the compound comprises at least one fluoro. In some embodiments, the compound comprises at least one fluoro (e.g., 1-10 fluoro, such as 1-5 fluoro, 1-4 fluoro, or 1-3 fluoro). In some embodiments, the compound comprises at least two fluoro (e.g., 2-10 fluoro, such as 2-5 fluoro, 2-4 fluoro, or 2-3 fluoro). In certain preferred embodiments, the compound comprises 2 or 3 fluoro. The fluoro can be found at various locations in the molecule, for example in R1, R1a, R3, R3a, R10, or a combination thereof. In certain Attorney Docket No.91392-415912 embodiments, when the compound has two or more fluoro, the two or more fluoro can be found on the same carbon (i.e., geminal), on adjacent carbons, or separated by more than one carbon. In some embodiments, ring A is aryl (e.g., C6-C10 aryl) or cycloalkenyl (e.g., C3-C12 cycloalkenyl). In some embodiments, ring A is phenyl or C3-C12cycloalkenyl (e.g., C6cycloalkenyl, such as cyclohexenyl, cyclohexenone, cyclohexadienyl, or cyclohexadienone). In some embodiments, ring A is phenyl. In some embodiments, ring A is cycloalkenyl (e.g., cyclohexenyl, cyclohexenone, cyclohexadienyl, or cyclohexadienone). In some embodiments, when ring A is aryl (e.g., C6-C10aryl, such as phenyl), then o is 1. In some embodiments, when ring A is cycloalkenyl (e.g., C3-C12 cycloalkenyl), then o is 0. In some embodiments, when ring A is aryl (e.g., C6-C10aryl, such as phenyl), then RAis -O-R10(e.g., hydroxyl, alkoxy, haloalkoxy, ester, or sulfonate). In some embodiments, when ring A is aryl (e.g., C6-C10aryl, such as phenyl), then o is 1, and RAis hydroxyl, alkoxy, haloalkoxy, ester, or sulfonate, wherein each alkoxy, haloalkoxy, ester, or sulfonate is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. For example, ring A may be phenyl, which can be represented by the following structure: ring A may be cycloalkenyl, the following structures: . In A-I, A-II, or A-III: I) Attorney Docket No.91392-415912 , , or a each of R4, R5, R6and R7is independently H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6 haloalkyl); each of R8and R9is independently halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl); R10is H, alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)- haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; each RBis independently halogen (e.g., fluoro), alkyl (e.g., C1-C10 alkyl), or haloalkyl (e.g., C1-C10haloalkyl); and m is 1, 2, 3, or 4. In some embodiments, the compound (e.g., a compound of formula A) is of formula A-I: Attorney Docket No.91392-415912 I) or a 4 each of R , R5, R6, haloalkyl; each of R8and R9is independently halogen, alkyl, or haloalkyl; R10is H, alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; each RBis independently halogen, alkyl, or haloalkyl; each of Ra, Rb, and Rc, when present, is independently H, alkyl, or haloalkyl; and m is 1, 2, or 3. In some embodiments, the compound (e.g., a compound of formula A) is of formula A-II or A-III: , Attorney Docket No.91392-415912 or a 45 each of R , R , each of R8and R9is independently halogen, alkyl, or haloalkyl; each RBis independently halogen, alkyl, or haloalkyl; and m is 1, 2, 3, or 4. In some embodiments, RAis hydroxyl, alkoxy (e.g., C1-C6alkoxy), haloalkoxy (e.g., C1- C6 haloalkoxy), ester (e.g., -OC(O)-alkyl or -OC(O)-haloalkyl), or sulfonate (e.g., -OS(O)2-alkyl or -OS(O)2-haloalkyl), wherein each alkoxy (e.g., C1-C6alkoxy), haloalkoxy (e.g., C1-C6haloalkoxy), ester (e.g., -OC(O)-alkyl or -OC(O)-haloalkyl), or sulfonate (e.g., -OS(O)2-alkyl or -OS(O)2-haloalkyl) is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, RAis hydroxyl, alkoxy (e.g., C1-C6 alkoxy), haloalkoxy (e.g., C1-C6 haloalkoxy), or sulfonate (e.g., -OS(O)2-alkyl or -OS(O)2- haloalkyl), wherein each alkoxy (e.g., C1-C6 alkoxy), haloalkoxy (e.g., C1-C6 haloalkoxy), or sulfonate (e.g., -OS(O)2-alkyl or -OS(O)2-haloalkyl) is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, RAis hydroxyl, alkoxy, haloalkoxy, ester, or sulfonate. In some embodiments, RAis hydroxyl, alkoxy, haloalkoxy, or sulfonate. In some embodiments, RAis hydroxyl, alkoxy, or sulfonate. In some embodiments, RAis hydroxyl. In some embodiments, RAis alkoxy or sulfonate. In some embodiments, RAis alkoxy (e.g., C1-C6alkoxy). Examples of RAbeing alkoxy include -OCH3, -OCFH2, -OCF2H, and -OCF3, and each of -OCH3, -OCFH2 and - OCF2H can be optionally substituted by one or more substituent (e.g., -C(O)ORa, such as -COOH). In some embodiments, RAis haloalkoxy or sulfonate. In some embodiments, RAis haloalkoxy (e.g., C1-C6haloalkoxy). Examples of RAbeing haloalkoxy include -OCFH2, -OCF2H, and -OCF3, and each of -OCFH2 and -OCF2H can be optionally substituted by one or more substituent (e.g., -C(O)ORa, such as -COOH). In some embodiments, RAis sulfonate (e.g., -OS(O)2-alkyl or -OS(O)2-haloalkyl). Examples of RAbeing sulfonate include -OS(O)2-CH3, - OS(O)2-CH2F, -OS(O)2-CHF2, and -OS(O)2-CF3, and each of -OS(O)2-CH3, -OS(O)2-CH2F, and Attorney Docket No.91392-415912 -OS(O)2-CHF2can be optionally substituted by one or more substituent (e.g., halogen, such as fluoro). In some embodiments, RAis alkoxy, ester, or sulfonate, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, RAis alkoxy or sulfonate, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, RAis haloalkoxy or sulfonate, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, RAis alkoxy optionally substituted with halogen, -C(O)ORa, or a combination thereof. In some embodiments, RAis alkoxy optionally substituted with -C(O)ORa. In some embodiments, RAis haloalkoxy optionally substituted with -C(O)ORa. In some embodiments, RAis sulfonate optionally substituted with halogen. In some embodiments, RAis hydroxyl. In some embodiments, RAis -O-R10. In some embodiments, RAis selected from the group consisting of -OH, -OCFH2, -OCF2H, -OCF3, -OCF2COOH, and -OS(O)2-CF3. In some embodiments, RAis selected from the group consisting of -OH, -OCF2H, -OCF3, -OCF2COOH, and -OS(O)2-CF3. In some embodiments, RAis selected from the group consisting of -OCF2H, -OCF3, -OCF2COOH, and -OS(O)2-CF3. In some embodiments, each RBis independently halogen, alkyl (e.g., C1-C10 alkyl, C2-C8 alkyl, or C1-C6alkyl), or haloalkyl (e.g., C1-C10haloalkyl, C2-C8haloalkyl, or C1-C6haloalkyl). In some embodiments, each RBis independently halogen or alkyl (e.g., C1-C10 alkyl, C2-C8 alkyl, or C1-C6alkyl). In some embodiments, RBis halogen (e.g., fluoro). In some embodiments, at least one of RBis halogen (e.g., fluoro). In some embodiments, at least two of RBis halogen (e.g., fluoro). In some embodiments, RBis C1-C10 alkyl (e.g., C2-C8 alkyl or C1-C6 alkyl). In some embodiments, RBis butyl, pentyl, or hexyl. In some embodiments, RBis pentyl (e.g., n-pentyl). In some embodiments, at least one RBis C1-C10 alkyl (e.g., C1-C6 alkyl). In certain preferred embodiments, one RBis C1-C10 alkyl (e.g., C1-C6 alkyl, such as n-pentyl). In some embodiments, one of RBis C1-C10 alkyl (e.g., C1-C6 alkyl, such as n-pentyl), and 0, 1, 2, or 3 of RBis halogen (e.g., fluoro). In some embodiments, one of RBis C1-C10alkyl (e.g., C1-C6alkyl, such as n- pentyl), and 1, 2, or 3 of RBis halogen (e.g., fluoro). In some embodiments, o is 0 or 1. In some embodiments, o is 0. In some embodiments, o is 1. In some embodiments, m is 1, 2, 3, or 4. In some embodiments, m is 1, 2, or 3. In some embodiments, m is 1 or 2. In some embodiments, m is 2 or 3. In some embodiments, m is 3 or 4. Attorney Docket No.91392-415912 In some embodiments, m is 1. In some embodiments, m is 2. In some embodiments, m is 3. In some embodiments, m is 4. In some embodiments, the compound (e.g., a compound of formula A) is of formula I, II, or III: , , , or a each of R1, R2, and R3is independently H, halogen, or alkyl; each of R4, R5, R6, and R7is independently H, halogen, or alkyl; each of R8and R9is independently halogen or alkyl; and each of R1aand R3a, when present, is independently H, halogen, or alkyl. Attorney Docket No.91392-415912 In some embodiments, the compound (e.g., a compound of formula A or A-I) is of formula I: , each of R1, R2, and R3is independently H, halogen, or alkyl; and each of R4, R5, R6, and R7is independently H, halogen, or alkyl; each of R8and R9is independently halogen or alkyl. In some embodiments, the compound (e.g., a compound of formula A or A-II) is of formula II: R5, or a pharmaceutically acceptable salt thereof, wherein each of R1, R2, and R3is independently H, halogen, or alkyl; each of R4, R5, R6, and R7is independently H, halogen, or alkyl; each of R8and R9is independently halogen or alkyl; and R1ais independently H, halogen, or alkyl. In some embodiments, the compound (e.g., a compound of formula A or A-III) is of formula III: Attorney Docket No.91392-415912 , or a each of R1, R2, each of R4, R5, R6, and R7is independently H, halogen, or alkyl; each of R8and R9is independently halogen or alkyl; and R3ais independently H, halogen, or alkyl. In some embodiments, the compound (e.g., a compound of formula I, II, or III) is of formula IV, V, or VI: , , Attorney Docket No.91392-415912 , or a 1 each of R and ; each of R1aand R3a, when present, is independently H, halogen, or alkyl (e.g., C1-C6alkyl). In some embodiments, the compound (e.g., a compound of formula A, A-I, or I) is of formula IV: , or a each of R1and R3is independently H, halogen, or alkyl. In some embodiments, the compound (e.g., a compound of formula A, A-II, or II) is of formula V:

[0003] Attorney Docket No.91392-415912 , or a 1 each of R and R1ais H, halogen, or alkyl. In some embodiments, the compound (e.g., a compound of formula A, A-III, or III) is of formula VI: , or a each of R1and R3is independently H, halogen, or alkyl; and R3ais H, halogen, or alkyl. In some embodiments, the compound (e.g., a compound of formula A or A-I) is of formula VII: , Attorney Docket No.91392-415912 or a pharmaceutically acceptable salt thereof, wherein each of R1, R2, and R3is independently H or alkyl; each of R4, R5, R6, and R7is independently H or alkyl; each of R8and R9is independently alkyl; R10is alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; and each of Ra, Rb, and Rc, when present, is independently H, alkyl, or haloalkyl. In some embodiments, the compound (e.g., a compound of formula A or A-I) is of formula VII: , each of R4, R5, R6, R7, R8, and R9is independently H or C1-C6 alkyl; R10is C1-C6alkyl, -C(O)-C1-C6alkyl, -S(O)2-C1-C6alkyl, wherein each C1-C6alkyl is optionally substituted with halogen, -C(O)Ra, -NRbRc, -C(O)ORa, -C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6 alkyl, wherein C1-C6 alkyl is optionally substituted with halogen. In some embodiments, the compound (e.g., a compound of formula A, A-I, or VII) is of formula VIII: , or a pharmaceutically Attorney Docket No.91392-415912 R10is alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; and each of Ra, Rb, and Rc, when present, is independently H, alkyl, or haloalkyl. In some embodiments, the compound (e.g., a compound of formula A, A-I, or VII) is of formula VIII: , or a R10is C1-C6 - - - 2- each C1-C6 alkyl is optionally substituted with halogen, -C(O)Ra, -NRbRc, -C(O)ORa, -C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen. In some embodiments, R1is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R1is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6alkyl). In some embodiments, R1is H or alkyl (e.g., C1-C6alkyl). In some embodiments, R1is H or halogen (e.g., fluoro). In some embodiments, R1is H. In some embodiments, R1is halogen (e.g., fluoro). In some embodiments, R1ais H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R1ais H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6alkyl). In some embodiments, R1ais H or halogen (e.g., fluoro). In some embodiments, R1ais H. In some embodiments, R1ais halogen (e.g., fluoro). In some embodiments, R2is H, halogen (e.g., fluoro), alkyl (e.g., C1-C10alkyl), or haloalkyl (e.g., C1-C10 haloalkyl). In some embodiments, R2is H, halogen (e.g., fluoro), or alkyl (e.g., C1-C10alkyl, C2-C8alkyl, or C1-C6alkyl). In some embodiments, R2is halogen (e.g., fluoro) or alkyl (e.g., C1-C10 alkyl, C2-C8 alkyl, or C1-C6 alkyl). In some embodiments, R2is alkyl (e.g., C1-C10alkyl, C2-C8alkyl, or C1-C6alkyl). In some embodiments, R2is C1-C6alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl). In some embodiments, R2is butyl, pentyl, or hexyl. In certain preferred embodiments, R2is pentyl (e.g., n-pentyl). Attorney Docket No.91392-415912 In some embodiments, R3is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R3is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6 alkyl). In some embodiments, R3is H or alkyl (e.g., C1-C6 alkyl). In some embodiments, R3is H or halogen (e.g., fluoro). In some embodiments, R3is H. In some embodiments, R3is halogen (e.g., fluoro). In some embodiments, R3ais H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R3ais H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6alkyl). In some embodiments, R3ais H or halogen (e.g., fluoro). In some embodiments, R3ais H. In some embodiments, R3ais halogen (e.g., fluoro). In some embodiments, R4is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R4is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6alkyl). In some embodiments, R4is H or alkyl (e.g., C1-C6alkyl, such as methyl). In certain preferred embodiments, R4is H. In some embodiments, R5is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, R5is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6 alkyl). In some embodiments, R5is H or alkyl (e.g., C1-C6 alkyl). In some embodiments, R5is alkyl (e.g., C1-C6alkyl, such as methyl). In certain preferred embodiments, R5is methyl. In some embodiments, R6is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, R6is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6 alkyl). In some embodiments, R6is H or alkyl (e.g., C1-C6 alkyl, such as methyl). In certain preferred embodiments, R6is H. In some embodiments, R7is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, R7is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6 alkyl). In some embodiments, R7is H or alkyl (e.g., C1-C6 alkyl, such as methyl). In certain preferred embodiments, R7is H. In some embodiments, R8is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R8is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6 alkyl). In some embodiments, R8is H or alkyl (e.g., C1-C6 alkyl). In some embodiments, R8is alkyl (e.g., C1-C6 alkyl, such as methyl). In certain preferred embodiments, R8is methyl. In some embodiments, R9is H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, R9is H, halogen (e.g., fluoro), or alkyl (e.g., C1- C6alkyl). In some embodiments, R9is H or alkyl (e.g., C1-C6alkyl). In some embodiments, R9is alkyl (e.g., C1-C6 alkyl, such as methyl). In certain preferred embodiments, R9is methyl. In some embodiments, R10comprises at least one fluoro (e.g., 1-10 fluoro, such as 1, 2, 3, 4, or 5 fluoro). In some embodiments, R10comprises 1, 2, 3, or 4 fluoro. In some embodiments, Attorney Docket No.91392-415912 R10comprises at least two fluoro (e.g., 2, 3, 4, or 5 fluoro). In some embodiments, R10comprises 2, 3, or 4 fluoro. In certain preferred embodiments, R10comprises 2 or 3 fluoro. In some embodiments, R10is H, alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6 haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6 haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2- haloalkyl is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is H, alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6 haloalkyl), -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -S(O)2-alkyl, or -S(O)2-haloalkyl is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, -C(O)NRbRc. In some embodiments, R10is C1-C6 alkyl, -C(O)-C1-C6 alkyl, or -S(O)2-C1-C6 alkyl, wherein each C1-C6 alkyl or -S(O)2-C1-C6alkyl is optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is C1- C6alkyl or -S(O)2-C1-C6alkyl, wherein each C1-C6alkyl or -S(O)2-C1-C6alkyl is optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is C1-C6alkyl or -S(O)2-C1-C6alkyl, wherein each C1-C6 alkyl or -S(O)2-C1-C6 alkyl is optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen or -C(O)ORa. In some embodiments, R10is H, alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2- alkyl, or -S(O)2-haloalkyl. In some embodiments, R10is H, alkyl, haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl. In some embodiments, R10is H, alkyl, or -S(O)2-alkyl. In some embodiments, R10is H. In some embodiments, R10is alkyl, haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl. In some embodiments, R10is alkyl or -S(O)2-alkyl. In some embodiments, R10is alkyl or haloalkyl. In some embodiments, R10is alkyl (e.g., C1-C6 alkyl). Examples of R10being alkyl include -CH3, - CFH2, -CF2H, and -CF3, and each of -CH3, -CFH2, -CF2H can be optionally substituted by one or more (e.g., 1, 2, or 3, such as 1 or 2) substituent (e.g., -C(O)ORa, such as -COOH). In some embodiments, R10is haloalkyl (e.g., C1-C6haloalkyl). Examples of R10being haloalkyl include - CFH2, -CF2H, and -CF3, and each of -CFH2 and -CF2H can be optionally substituted by one or Attorney Docket No.91392-415912 more (e.g., 1, 2, or 3, such as 1 or 2) substituent (e.g., -C(O)ORa, such as -COOH). In some embodiments, R10is -S(O)2-alkyl or -S(O)2-haloalkyl. In some embodiments, R10is -S(O)2-alkyl. Examples of R10being -S(O)2-alkyl include -S(O)2-CH3, -S(O)2-CH2F, -S(O)2-CF2H, and -S(O)2- CF3, and each of -S(O)2-CH3, -S(O)2-CH2F, -S(O)2-CF2H can be optionally substituted by one or more (e.g., 1, 2, or 3, such as 1 or 2) substituent (e.g., halogen, such as fluoro). Examples of R10being -S(O)2-haloalkyl include -S(O)2-CF2H, and -S(O)2-CF3, and -S(O)2-CH3. In some embodiments, R10is alkyl, haloalkyl, -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is alkyl, haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, each of which is independently optionally substituted with one or more (e.g., 1, 2, or 3, such as 1 or 2) of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc. In some embodiments, R10is alkyl optionally substituted with one or more of halogen or -C(O)ORa. In some embodiments, R10is alkyl or haloalkyl optionally substituted with -C(O)ORa. In some embodiments, R10is -S(O)2-alkyl optionally substituted with halogen. In some embodiments, R10is selected from the group consisting of H, -CFH2, -CF2H, -CF3, -CF2COOH, and -S(O)2-CF3. In some embodiments, R10is selected from the group consisting of H, -CF2H, -CF3, -CF2COOH, and -S(O)2-CF3. In some embodiments, R10is selected from the group consisting of H, -CFH2, -CF2H, -CF3, and -CF2COOH. In some embodiments, R10is selected from the group consisting of H, -CF2H, -CF3, and -CF2COOH. In some embodiments, R10is selected from the group consisting of -CFH2, -CF2H, -CF3, -CF2COOH, and -S(O)2-CF3. In some embodiments, R10is selected from the group consisting of -CF2H, -CF3, -CF2COOH, and -S(O)2-CF3. In some embodiments, R10is selected from the group consisting of -CFH2, -CF2H, -CF3, and -CF2COOH. In some embodiments, R10is selected from the group consisting of -CF2H, -CF3, and -CF2COOH. In some embodiments, each of Ra, Rb, and Rc, when present, is independently H, alkyl (e.g., C1-C6 alkyl, such as methyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, each of Ra, Rb, and Rc, when present, is independently H or C1-C6 alkyl (e.g., methyl). In some embodiments, each of Ra, Rb, and Rc, when present, is independently H. In some embodiments, each of Ra, Rb, and Rcis independently H or C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen. In some embodiments, Rais H or C1-C6 alkyl (e.g., methyl). In some embodiments, Rais H. In some embodiments, each of Rband Rcis independently H or C1-C6alkyl (e.g., methyl). In some embodiments, each of Rband Rcis H. In some embodiments, each of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl). In some Attorney Docket No.91392-415912 embodiments, each of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, is independently H or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R4, R5, R6, R7, R8, and R9is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl). In some embodiments, at least one (e.g., 1, 2, 3, or 4) of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. In some embodiments, at least two (e.g., 2, 3, or 4) of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. In some embodiments, 2 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. In some embodiments, 3 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. In some embodiments, at least one (e.g., 1, 2, or 3) of R1, R3, and R1aor R3a, when present, are fluoro. In some embodiments, at least two (e.g., 2 or 3) of R1, R3, and R1aor R3a, when present, are fluoro. In some embodiments, 2 of R1, R3, and R1aor R3a, when present, are fluoro. In some embodiments, 3 of R1, R3, and R1aor R3a, when present, are fluoro. In some embodiments, each of R1, R2, and R3is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R1, R2, and R3is independently H or alkyl (e.g., C1-C6alkyl). In some embodiments, each of R1, R2, and R3is independently halogen (e.g., fluoro) or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R1and R3is independently H, halogen, or alkyl (e.g., C1- C6 alkyl). In some embodiments, each of R1and R3is independently H or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R1and R3is independently H or halogen (e.g., fluoro). In some embodiments, each of R1and R3is H. In some embodiments, at least one of R1and R3is halogen (e.g., fluoro). In some embodiments, each of R1and R3is halogen (e.g., fluoro). In some embodiments, when one of R1aand R3ais present, then the other of R1aand R3ais absent. In some embodiments, when R1ais present, then both of R1and R1aare halogen (e.g., fluoro). In some embodiments, when R3ais present, then both of R3and R3aare halogen (e.g., fluoro). In some embodiments, each of R5, R8, and R9is independently halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, each of R5, R8, and R9is independently halogen or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R5, R8, and R9is independently C1-C6 alkyl (e.g., methyl). In certain preferred embodiments, each of R5, R8, and R9is methyl. In some embodiments, each of R8and R9is independently H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, each of R8and R9is independently halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6 haloalkyl). In some embodiments, each of R8, and R9is independently halogen or alkyl (e.g., C1- Attorney Docket No.91392-415912 C6alkyl). In some embodiments, each of R8and R9is independently C1-C6alkyl (e.g., methyl). In certain preferred embodiments, each of R8, and R9is methyl. In some embodiments, each of R4, R6, and R7is independently H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, each of R4, R6, and R7is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R4, R6, and R7is independently H or halogen (e.g., fluoro). In some embodiments, each of R4, R6, and R7is independently H or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R4, R6, and R7is H. In some embodiments, each of R6and R7is independently H, halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6haloalkyl). In some embodiments, each of R6and R7is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl). In some embodiments, each of R6and R7is independently H or alkyl (e.g., C1-C6alkyl). In some embodiments, each of R6and R7is H. In some embodiments, the compound is selected from the group consisting of , , Attorney Docket No.91392-415912 The following represent illustrative embodiments of compounds of the disclosure: # Structure 1 e Attorney Docket No.91392-415912 # Structure 4 e Attorney Docket No.91392-415912 8 e c In some embodiments, the disclosure relates to a method of preparing a compound according to the present disclosure comprising contacting a precursor cannabinoid compound with a fluorinating agent to provide the fluorinated cannabinoid compound. In some embodiments, the precursor cannabinoid compound is cannabinol (CBN). In some embodiments, the cannabinol (CBN) is of the formula: Attorney Docket No.91392-415912 , or a In some . In some embodiments, the contacting comprises an electrophilic fluorination reaction (i.e., fluorinating via an electrophilic reaction). In some embodiments, the contacting comprises an oxidation reaction (i.e., oxidizing). In some embodiments, the fluorinating agent is selected from the group consisting of N- fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), 1-chloromethyl- 4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4), and combinations thereof. In some embodiments, the fluorinating agent is selected from the group consisting of N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA- BF4). In some embodiments, the fluorinating agent is 1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4). In some embodiments, the fluorinating agent is an oxidizing agent. In some embodiments, the fluorinating agent is selected from the group consisting of CFH2OTf, CFH2I, CFH2Br, CFH2SONa, CFH2SOCl, CFH2SO2Na, CFH2SO2Cl, TMSCFH2, CF2HOTf, CF2HI, CF2HBr, CF2HSONa, CF2HSOCl, CF2HSO2Na, CF2HSO2Cl, TMSCF2H, CF3OTf, CF3I, CF3Br, CF3SONa, CF3SOCl, CF3SO2Na, CF3SO2Cl, TMSCF3 (CF3SiMe3), Tf2O, BrCF2COONa, 1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (3,3-Dimethyl-1- (trifluoromethyl)-1,2-benziodoxole), 5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate (5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate), and TT-CF3+OTf−. In some embodiments, the fluorinating agent is in molar excess to the precursor cannabinoid compound. In some embodiments, a molar ratio of the fluorinating agent to the precursor compound is greater than about 1:1. In some embodiments, a molar ratio of the fluorinating agent to the precursor compound is about 1:1 to about 10:1 or about 1:1 to about 5:1 (e.g., about 1:1 to about 3:1, or about 1:1 to about 2:1). For example, a molar ratio of the fluorinating agent to the precursor compound may be about 1:1, about 2:1, about 3:1, about 4:1, or about 5:1. Attorney Docket No.91392-415912 In some embodiments, the contacting is performed in the presence of a solvent selected from the group comprising acetone, acetonitrile, dioxane, dimethylformamide, dimethyl sulfoxide, pyridine, nitromethane, toluene, water, and any combination thereof. In some embodiments, the contacting is performed in the presence of a solvent selected from the group comprising acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, pyridine, nitromethane, water, and any combination thereof. In some embodiments, the solvent is acetonitrile, dioxane, toluene, water, or any combination thereof. In some embodiments, the solvent is acetonitrile. In some embodiments, the contacting is performed at a temperature of about 20 °C to about 80 °C (e.g., about 20 °C to about 30 °C, about 25 °C to about 35 °C, about 20 °C to about 40 °C, about 50 °C to about 70 °C, or about 50 °C to about 80 °C). In some embodiments, the contacting is performed for about 1 hour to about 16 hours (e.g., about 1 hour to about 6 hours, about 3 hours to about 5 hours, or about 10 hours to about 14 hours). In some embodiments, the contacting is performed for about 1 hour to about 4 hours (e.g., about 2 hours). In some embodiments, the contacting is performed under basic conditions (e.g., in the presence of a base). In some embodiments, the contacting is performed in the presence of a base selected from the group consisting of NaH, NaOH, LiOH, KOH, and any combination thereof. In some embodiments, the contacting is performed in the presence of a base selected from the group consisting of NaH, LiOH, KOH, and any combination thereof. Those skilled in the art will recognize that the species listed or illustrated herein are not exhaustive, and that additional species within the scope of these defined terms may also be selected. Pharmaceutical Compositions For treatment purposes, pharmaceutical compositions comprising the compounds described herein may further comprise one or more pharmaceutically-acceptable excipients. A pharmaceutically-acceptable excipient is a substance that is non-toxic and otherwise biologically suitable for administration to a subject. Such excipients facilitate administration of the compounds described herein and are compatible with the active ingredient. Examples of pharmaceutically-acceptable excipients include stabilizers, lubricants, surfactants, diluents, anti- oxidants, binders, coloring agents, bulking agents, emulsifiers, or taste-modifying agents. In preferred embodiments, pharmaceutical compositions according to the disclosure are sterile compositions. Pharmaceutical compositions may be prepared using compounding techniques known or that become available to those skilled in the art. Attorney Docket No.91392-415912 Sterile compositions are also contemplated by the disclosure, including compositions that are in accord with national and local regulations governing such compositions. The pharmaceutical compositions and compounds described herein may be formulated as solutions, emulsions, suspensions, or dispersions in suitable pharmaceutical solvents or carriers, or as pills, tablets, lozenges, suppositories, sachets, dragees, granules, powders, powders for reconstitution, or capsules along with solid carriers according to conventional methods known in the art for preparation of various dosage forms. Pharmaceutical compositions of the disclosure may be administered by a suitable route of delivery, such as oral, parenteral, rectal, nasal, topical, or ocular routes, or by inhalation. Preferably, the compositions are formulated for intravenous or oral administration. For oral administration, the compounds the disclosure may be provided in a solid form, such as a tablet or capsule, or as a solution, emulsion, or suspension. To prepare the oral compositions, the compounds of the disclosure may be formulated to yield a dosage of, e.g., from about 0.1 mg to 1 g daily, or about 1 mg to 50 mg daily, or about 50 to 250 mg daily, or about 250 mg to 1 g daily. Oral tablets may include the active ingredient(s) mixed with compatible pharmaceutically acceptable excipients such as diluents, disintegrating agents, binding agents, lubricating agents, sweetening agents, flavoring agents, coloring agents and preservative agents. Suitable inert fillers include sodium and calcium carbonate, sodium and calcium phosphate, lactose, starch, sugar, glucose, methyl cellulose, magnesium stearate, mannitol, sorbitol, and the like. Exemplary liquid oral excipients include ethanol, glycerol, water, and the like. Starch, polyvinyl-pyrrolidone (PVP), sodium starch glycolate, microcrystalline cellulose, and alginic acid are exemplary disintegrating agents. Binding agents may include starch and gelatin. The lubricating agent, if present, may be magnesium stearate, stearic acid, or talc. If desired, the tablets may be coated with a material such as glyceryl monostearate or glyceryl distearate to delay absorption in the gastrointestinal tract, or may be coated with an enteric coating. Capsules for oral administration include hard and soft gelatin capsules. To prepare hard gelatin capsules, active ingredient(s) may be mixed with a solid, semi-solid, or liquid diluent. Soft gelatin capsules may be prepared by mixing the active ingredient with water, an oil, such as peanut oil or olive oil, liquid paraffin, a mixture of mono and di-glycerides of short chain fatty acids, polyethylene glycol 400, or propylene glycol. Liquids for oral administration may be in the form of suspensions, solutions, emulsions, or syrups, or may be lyophilized or presented as a dry product for reconstitution with water or other suitable vehicle before use. Such liquid compositions may optionally contain: pharmaceutically-acceptable excipients such as suspending agents (for example, sorbitol, methyl cellulose, sodium alginate, gelatin, hydroxyethylcellulose, carboxymethylcellulose, aluminum Attorney Docket No.91392-415912 stearate gel and the like); non-aqueous vehicles, e.g., oil (for example, almond oil or fractionated coconut oil), propylene glycol, ethyl alcohol, or water; preservatives (for example, methyl or propyl p-hydroxybenzoate or sorbic acid); wetting agents such as lecithin; and, if desired, flavoring or coloring agents. For parenteral use, including intravenous, intramuscular, intraperitoneal, intranasal, or subcutaneous routes, the agents of the disclosure may be provided in sterile aqueous solutions or suspensions, buffered to an appropriate pH and isotonicity or in parenterally acceptable oil. Suitable aqueous vehicles include Ringer's solution and isotonic sodium chloride. Such forms may be presented in unit-dose form such as ampoules or disposable injection devices, in multi- dose forms such as vials from which the appropriate dose may be withdrawn, or in a solid form or pre-concentrate that can be used to prepare an injectable formulation. Illustrative infusion doses range from about 1 to 1000 μg / kg / minute of agent admixed with a pharmaceutical carrier over a period ranging from several minutes to several days. For nasal, inhaled, or oral administration, the inventive pharmaceutical compositions may be administered using, for example, a spray formulation also containing a suitable carrier. The inventive compositions may be formulated for rectal administration as a suppository. For topical applications, the compounds of the present disclosure are preferably formulated as creams or ointments or a similar vehicle suitable for topical administration. For topical administration, the inventive compounds may be mixed with a pharmaceutical carrier at a concentration of about 0.1% to about 10% of drug to vehicle. Another mode of administering the agents of the disclosure may utilize a patch formulation to effect transdermal delivery. As used herein, the terms “treat” or “treatment” encompass both “preventative” and “curative” treatment. “Preventative” treatment is meant to indicate a postponement of development of a disease, a symptom of a disease, or medical condition, suppressing symptoms that may appear, or reducing the risk of developing or recurrence of a disease or symptom. “Curative” treatment includes reducing the severity of or suppressing the worsening of an existing disease, symptom, or condition. Thus, treatment includes ameliorating or preventing the worsening of existing disease or condition symptoms, preventing additional symptoms from occurring, ameliorating or preventing the underlying systemic causes of symptoms, inhibiting the disorder or disease, e.g., arresting the development of the disorder or disease, relieving the disorder or disease, causing regression of the disorder or disease, relieving a condition caused by the disease or disorder, or stopping the symptoms of the disease or disorder. The term “subject” or “patient,” as used herein, means an animal, preferably a mammal, and most preferably a human in need of such treatment, such as a human. Attorney Docket No.91392-415912 Exemplary diseases or conditions include appetite-loss (e.g., nausea), sleeping disorders (e.g., insomnia), glaucoma, pain (e.g., myofascial pain), convulsive disorders (e.g., epilepsy), cancer (e.g., breast cancer, prostate cancer), bone cell growth disorders, inflammatory disorders, amyotrophic lateral sclerosis (ALS), and Alzheimer’s disease. In some examples, the disease or condition is pain. In some embodiments, methods of treatment include treating appetite-loss (e.g., nausea), sleeping disorders (e.g., insomnia), glaucoma, pain (e.g., mayofascial pain), convulsive disorders (e.g., epilepsy), cancer (e.g., breast cancer, prostate cancer), bone cell growth disorders, inflammatory disorders, amyotrophic lateral sclerosis (ALS), and Alzheimer’s disease. In some embodiments, the disclosure provides a pharmaceutical composition comprising at least one compound of the present disclosure, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients (e.g., carriers or vehicles). In some embodiments, the disclosure provides a pharmaceutical composition comprising an effective amount of the compound of the present disclosure, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable excipients (e.g., carriers or vehicles). In some embodiments, the disclosure provides a method of treating a disease or condition in a patient comprising administering to the patient a compound, a pharmaceutically acceptable salt thereof, or a pharmaceutical composition of the present disclosure. In some embodiments, the disclosure provides a method of treating a disease or condition in a patient comprising administering to the patient in need of such treatment an effective amount of a compound, a pharmaceutically acceptable salt thereof, or a pharmaceutical composition of the present disclosure. In some embodiments, the disclosure provides a method of treating a disease or a condition (e.g., appetite-loss (e.g., nausea), sleeping disorders (e.g., insomnia), glaucoma, pain (e.g., mayofascial pain), convulsive disorders (e.g., epilepsy), cancer (e.g., breast cancer, prostate cancer), bone cell growth disorders, inflammatory disorders, amyotrophic lateral sclerosis (ALS), and Alzheimer’s disease) comprising administering to a subject in need of such treatment an effective amount of a compound of the present disclosure, or a pharmaceutically acceptable salt thereof. In one aspect, the compounds and pharmaceutical compositions of the disclosure specifically target CB1, CB2, and / or vanilloid receptors. In some embodiments, the compounds and pharmaceutical compositions of the disclosure specifically target CB1 and / or CB2 receptors. Thus, the compounds and pharmaceutical compositions of the disclosure may be used to prevent, reverse, slow, or inhibit the activity of these receptors. For example, activation / inhibition of CB1 and CB2 receptors and other receptors may influence several physiological changes, such as Attorney Docket No.91392-415912 inhibition of proteins that activate IL-2 production. In some embodiments, the compounds of the disclosure function as agonists or partial agonists to CB1, CB2, and / or vanilloid receptors. CB1 and CB2 receptors are part of the endocannabinoid system (ECS), which regulates and controls many of critical bodily functions such as learning and memory, emotional processing, sleep, temperature control, pain control, inflammatory and immune responses, and eating. The CB1 receptor predominantly in the central nervous system (e.g., brain) and regulates sleep, appetite, time perception, short-term memory, and coordination. The CB2 receptor is present on immune system cells where it influences pain, inflammation, and tissue damage. The CB2 receptor is critical to helping control immune functioning, playing a role in modulating intestinal inflammation, contraction, and pain in inflammatory bowel conditions. In the inhibitory methods of the disclosure, an “effective amount” means an amount sufficient to inhibit the target protein. Measuring such target modulation may be performed by routine analytical methods such as those described below. Such modulation is useful in a variety of settings, including in vitro assays. In treatment methods according to the disclosure, an “effective amount” means an amount or dose sufficient to generally bring about the desired therapeutic benefit in subjects needing such treatment. Effective amounts or doses of the compounds of the disclosure may be ascertained by routine methods, such as modeling, dose escalation, or clinical trials, taking into account routine factors, e.g., the mode or route of administration or drug delivery, the pharmacokinetics of the agent, the severity and course of the infection, the subject’s health status, condition, and weight, and the judgment of the treating physician. An exemplary dose is in the range of about from about 0.1 mg to 1 g daily, or about 1 mg to 50 mg daily, or about 50 to 250 mg daily, or about 250 mg to 1 g daily. The total dosage may be given in single or divided dosage units (e.g., BID, TID, QID). Once improvement of the patient’s disease has occurred, the dose may be adjusted for preventative or maintenance treatment. For example, the dosage or the frequency of administration, or both, may be reduced as a function of the symptoms, to a level at which the desired therapeutic or prophylactic effect is maintained. Of course, if symptoms have been alleviated to an appropriate level, treatment may cease. Patients may, however, require intermittent treatment on a long-term basis upon any recurrence of symptoms. Patients may also require chronic treatment on a long-term basis. Drug Combinations The inventive compounds described herein may be used in pharmaceutical compositions or methods in combination with one or more additional active ingredients in the treatment of the Attorney Docket No.91392-415912 diseases and disorders described herein. Further additional active ingredients include other therapeutics or agents that mitigate adverse effects of therapies for the intended disease targets. Such combinations may serve to increase efficacy, ameliorate other disease symptoms, decrease one or more side effects, or decrease the required dose of an inventive compound. The additional active ingredients may be administered in a separate pharmaceutical composition from a compound of the present disclosure or may be included with a compound of the present disclosure in a single pharmaceutical composition. The additional active ingredients may be administered simultaneously with, prior to, or after administration of a compound of the present disclosure. Combination agents include additional active ingredients are those that are known or discovered to be effective in treating the diseases and disorders described herein, including those active against another target associated with the disease. For example, compositions and formulations of the disclosure, as well as methods of treatment, can further comprise other drugs or pharmaceuticals, e.g., other active agents useful for treating or palliative for the target diseases or related symptoms or conditions. The pharmaceutical compositions described herein may additionally comprise one or more of such active agents, and methods of treatment may additionally comprise administering an effective amount of one or more of such active agents. ALTERNATIVE EMBODIMENTS Various additional embodiments of the invention are provided throughout the present disclosure. For instance, the following numbered clauses are contemplated and are non-limiting: 1. A fluorinated cannabinoid compound, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is comprised of the formula (I), (II), or (III) , Attorney Docket No.91392-415912 R5, , or a wherein each of R1, R2, and R3is independently H, halogen, or C1-C6alkyl; each of R4, R5, R6, R7, R8, and R9is independently H, halogen, or C1-C6 alkyl; and each of R1aand R3a, when present, is independently H, halogen, or C1-C6alkyl. 2. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound comprises at least two fluoro. 3. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 4. The fluorinated cannabinoid compound of clause 3, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 5. The fluorinated cannabinoid compound of clause 3, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. Attorney Docket No.91392-415912 6. The fluorinated cannabinoid compound of clause 3, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 7. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R3, and R1aand R3a, when present, are fluoro. 8. The fluorinated cannabinoid compound of clause 7, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R3, and R1aand R3a, when present, are fluoro. 9. The fluorinated cannabinoid compound of clause 8, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R3, and R1aand R3a, when present, are fluoro. 10. The fluorinated cannabinoid compound of clause 8, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R3, and R1aand R3a, when present, are fluoro. 11. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or halogen. 12. The fluorinated cannabinoid compound of clause 11, any other suitable clause, or any combination of suitable clauses, wherein R1is H or halogen. 13. The fluorinated cannabinoid compound of clause 12, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 14. The fluorinated cannabinoid compound of clause 12, any other suitable clause, or any combination of suitable clauses, wherein R1is halogen. 15. The fluorinated cannabinoid compound of clause 14, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 16. The fluorinated cannabinoid compound of clause 11, any other suitable clause, or any combination of suitable clauses, wherein R3is H or halogen. 17. The fluorinated cannabinoid compound of clause 16, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 18. The fluorinated cannabinoid compound of clause 16, any other suitable clause, or any combination of suitable clauses, wherein R3is halogen. 19. The fluorinated cannabinoid compound of clause 18, any other suitable clause, or any combination of suitable clauses, wherein R3is fluoro. Attorney Docket No.91392-415912 20. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein each of R1aand R3a, when present, is independently H or halogen. 21. The fluorinated cannabinoid compound of clause 20, any other suitable clause, or any combination of suitable clauses, wherein R1ais H or halogen. 22. The fluorinated cannabinoid compound of clause 21, any other suitable clause, or any combination of suitable clauses, wherein R1ais H. 23. The fluorinated cannabinoid compound of clause 21, any other suitable clause, or any combination of suitable clauses, wherein R1ais halogen. 24. The fluorinated cannabinoid compound of clause 23, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 25. The fluorinated cannabinoid compound of clause 20, any other suitable clause, or any combination of suitable clauses, wherein R3ais H or halogen. 26. The fluorinated cannabinoid compound of clause 25, any other suitable clause, or any combination of suitable clauses, wherein R3ais H. 27. The fluorinated cannabinoid compound of clause 25, any other suitable clause, or any combination of suitable clauses, wherein R3ais halogen. 28. The fluorinated cannabinoid compound of clause 27, any other suitable clause, or any combination of suitable clauses, wherein R3ais fluoro. 29. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein each of R2, R5, R8, and R9is independently C1-C6alkyl. 30. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein R2is C1-C6 alkyl. 31. The fluorinated cannabinoid compound of clause 30, any other suitable clause, or any combination of suitable clauses, wherein R2is pentyl. 32. The fluorinated cannabinoid compound of clause 30, any other suitable clause, or any combination of suitable clauses, wherein R2is n-pentyl. 33. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein R5is C1-C6alkyl. 34. The fluorinated cannabinoid compound of clause 33, any other suitable clause, or any combination of suitable clauses, wherein R5is methyl. 35. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein R8is C1-C6alkyl. Attorney Docket No.91392-415912 36. The fluorinated cannabinoid compound of clause 35, any other suitable clause, or any combination of suitable clauses, wherein R8is methyl. 37. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein R9is C1-C6alkyl. 38. The fluorinated cannabinoid compound of clause 37, any other suitable clause, or any combination of suitable clauses, wherein R9is methyl. 39. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is C1-C6alkyl. 40. The fluorinated cannabinoid compound of clause 39, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is methyl. 41. The fluorinated cannabinoid compound of clause 29, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is C1-C6alkyl. 42. The fluorinated cannabinoid compound of clause 41, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is methyl. 43. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein each of R4, R6, and R7is H. 44. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or halogen; each of R2, R5, R8, and R9is independently C1-C6 alkyl; each of R4, R6, and R7is H; and each of R1aand R3a, when present, is independently H or halogen. 45. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or fluoro; each of R2, R5, R8, and R9is independently C1-C6 alkyl; each of R4, R6, R7, is H; and each of R1aand R3a, when present, is independently H or fluoro. 46. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (IV), (V), or (VI) Attorney Docket No.91392-415912 , , , or a wherein each of R1and R3is independently H, halogen, or C1-C6 alkyl; and each of R1aand R3a, when present, is independently H, halogen, or C1-C6alkyl. 47. The fluorinated cannabinoid compound of clause 46, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound comprises at least two fluoro. Attorney Docket No.91392-415912 48. The fluorinated cannabinoid compound of clause 47, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R3, and R1aand R3a, when present, are fluoro. 49. The fluorinated cannabinoid compound of clause 48, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R3, and R1aand R3a, when present, are fluoro. 50. The fluorinated cannabinoid compound of clause 49, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R3, and R1aand R3a, when present, are fluoro. 51. The fluorinated cannabinoid compound of clause 49, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R3, and R1aand R3a, when present, are fluoro. 52. The fluorinated cannabinoid compound of clause 46, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or halogen. 53. The fluorinated cannabinoid compound of clause 52, any other suitable clause, or any combination of suitable clauses, wherein R1is H or halogen. 54. The fluorinated cannabinoid compound of clause 53, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 55. The fluorinated cannabinoid compound of clause 53, any other suitable clause, or any combination of suitable clauses, wherein R1is halogen. 56. The fluorinated cannabinoid compound of clause 55, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 57. The fluorinated cannabinoid compound of clause 52, any other suitable clause, or any combination of suitable clauses, wherein R3is H or halogen. 58. The fluorinated cannabinoid compound of clause 57, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 59. The fluorinated cannabinoid compound of clause 57, any other suitable clause, or any combination of suitable clauses, wherein R3is halogen. 60. The fluorinated cannabinoid compound of clause 59, any other suitable clause, or any combination of suitable clauses, wherein R3is fluoro. 61. The fluorinated cannabinoid compound of clause 46, any other suitable clause, or any combination of suitable clauses, wherein each of R1aand R3a, when present, is independently H or halogen. 62. The fluorinated cannabinoid compound of clause 61, any other suitable clause, or any combination of suitable clauses, wherein R1ais H or halogen. Attorney Docket No.91392-415912 63. The fluorinated cannabinoid compound of clause 62, any other suitable clause, or any combination of suitable clauses, wherein R1ais H. 64. The fluorinated cannabinoid compound of clause 62, any other suitable clause, or any combination of suitable clauses, wherein R1ais halogen. 65. The fluorinated cannabinoid compound of clause 64, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 66. The fluorinated cannabinoid compound of clause 61, any other suitable clause, or any combination of suitable clauses, wherein R3ais H or halogen. 67. The fluorinated cannabinoid compound of clause 66, any other suitable clause, or any combination of suitable clauses, wherein R3ais H. 68. The fluorinated cannabinoid compound of clause 66, any other suitable clause, or any combination of suitable clauses, wherein R3ais halogen. 69. The fluorinated cannabinoid compound of clause 68, any other suitable clause, or any combination of suitable clauses, wherein R3ais fluoro. 70. The fluorinated cannabinoid compound of clause 46, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or halogen; and each of R1aand R3a, when present, is independently H or halogen. 71. The fluorinated cannabinoid compound of clause 46, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or fluoro; and each of R1aand R3a, when present, is independently H or fluoro. 72. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of

[0004] Attorney Docket No.91392-415912 , 73. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of Attorney Docket No.91392-415912 , , 74. A pharmaceutical composition comprising a therapeutically effective amount of the fluorinated cannabinoid compound of any one of clauses 1 to 73, any other suitable clause, or any combination of suitable clauses, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or vehicles. 75. A method of treating a disease in a patient comprising administering to the patient the fluorinated cannabinoid compound of any one of clauses 1 to 73, any other suitable clause, or any combination of suitable clauses, or a pharmaceutically acceptable salt thereof. 76. The method of clause 75, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor or the CB2 receptor. 77. The method of clause 76, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds the CB1 receptor or the CB2 receptor. Attorney Docket No.91392-415912 78. The method of clause 76, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor. 79. The method of clause 76, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB2 receptor. 80. The method of clause 75, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor and the CB2 receptor. 81. The method of clause 80, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds the CB1 receptor and the CB2 receptor. 82. The method of clause 75, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a vanilloid receptor. 83. A method of treating a disease in a patient comprising administering to the patient the fluorinated cannabinoid compound of any one of clauses 1 to 73, any other suitable clause, or any combination of suitable clauses, or a pharmaceutically acceptable salt thereof, or the pharmaceutical composition of clause 74, any other suitable clause, or any combination of suitable clauses. 84. The method of clause 83, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor or a CB2 receptor. 85. The method of clause 84, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds a CB1 receptor or a CB2 receptor. 86. The method of clause 84, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor. 87. The method of clause 84, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB2 receptor. 88. The method of clause 83, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor and a CB2 receptor. 89. The method of clause 88, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds a CB1 receptor and a CB2 receptor. 90. The method of clause 83, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a vanilloid receptor. 91. A method of preparing a fluorinated cannabinoid compound comprising contacting a precursor cannabinoid compound with a fluorinating agent to provide the fluorinated cannabinoid compound. 92. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the precursor cannabinoid compound is cannabinol (CBN). Attorney Docket No.91392-415912 93. The method of clause 92, any other suitable clause, or any combination of suitable clauses, wherein the cannabinol (CBN) is of the formula , or a 94. The of suitable clauses, wherein the fluorinating agent is selected from the group consisting of N-fluoro-o- benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and 1-chloromethyl-4- fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4). 95. The method of clause 94, any other suitable clause, or any combination of suitable clauses, wherein the fluorinating agent is 1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F-TEDA-BF4). 96. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the molar ratio of fluorinating agent to the precursor cannabinoid compound is of from about 1:1 to about 5:1. 97. The method of clause 96, any other suitable clause, or any combination of suitable clauses, wherein the molar ratio of fluorinating agent to the precursor cannabinoid compound is of from about 1:1 to about 3:1. 98. The method of clause 97, any other suitable clause, or any combination of suitable clauses, wherein the molar ratio of fluorinating agent to the precursor cannabinoid compound is of from about 1:1 to about 2:1. 99. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the contacting is an electrophilic fluorination reaction. 100. The method of clause 99, any other suitable clause, or any combination of suitable clauses, wherein the contacting is an oxidation reaction. 101. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed in the presence of a solvent selected from the group comprising acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, pyridine, nitromethane, water, and any combination thereof. Attorney Docket No.91392-415912 102. The method of clause 101, any other suitable clause, or any combination of suitable clauses, wherein the solvent is acetonitrile. 103. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed at a temperature of about 25 °C to about 35 °C. 104. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 1 hour to about 4 hours. 105. The method of clause 104, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 2 hours. 106. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the fluorinating agent is in molar excess to the precursor cannabinoid compound. 107. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (I), (II), or (III) , , Attorney Docket No.91392-415912 , alkyl; each of R4, R5, R6, R7, R8, and R9is independently H, halogen, or C1-C6 alkyl; and each of R1aand R3a, when present, is independently H, halogen, or C1-C6 alkyl. 108. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound comprises at least two fluoro. 109. The method of clause 108, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 110. The method of clause 109, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 111. The method of clause 109, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 112. The method of clause 109, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R2, R3, R4, R5, R6, R7, R8, R9, and R1aand R3a, when present, are fluoro. 113. The method of clause 108, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R3, and R1aand R3a, when present, are fluoro. 114. The method of clause 113, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R3, and R1aand R3a, when present, are fluoro. 115. The method of clause 114, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R3, and R1aand R3a, when present, are fluoro. Attorney Docket No.91392-415912 116. The method of clause 114, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R3, and R1aand R3a, when present, are fluoro. 117. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or halogen. 118. The method of clause 117, any other suitable clause, or any combination of suitable clauses, wherein R1is H or halogen. 119. The method of clause 118, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 120. The method of clause 118, any other suitable clause, or any combination of suitable clauses, wherein R1is halogen. 121. The method of clause 120, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 122. The method of clause 117, any other suitable clause, or any combination of suitable clauses, wherein R3is H or halogen. 123. The method of clause 122, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 124. The method of clause 122, any other suitable clause, or any combination of suitable clauses, wherein R3is halogen. 125. The method of clause 124, any other suitable clause, or any combination of suitable clauses, wherein R3is fluoro. 126. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein each of R1aand R3a, when present, is independently H or halogen. 127. The method of clause 126, any other suitable clause, or any combination of suitable clauses, wherein R1ais H or halogen. 128. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein R1ais H. 129. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein R1ais halogen. 130. The method of clause 129, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 131. The method of clause 126, any other suitable clause, or any combination of suitable clauses, wherein R3ais H or halogen. 132. The method of clause 131, any other suitable clause, or any combination of suitable clauses, wherein R3ais H. Attorney Docket No.91392-415912 133. The method of clause 131, any other suitable clause, or any combination of suitable clauses, wherein R3ais halogen. 134. The method of clause 133, any other suitable clause, or any combination of suitable clauses, wherein R3ais fluoro. 135. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein each of R2, R5, R8, and R9is independently C1-C6alkyl. 136. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein R2is C1-C6alkyl. 137. The method of clause 136, any other suitable clause, or any combination of suitable clauses, wherein R2is pentyl. 138. The method of clause 136, any other suitable clause, or any combination of suitable clauses, wherein R2is n-pentyl. 139. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein R5is C1-C6 alkyl. 140. The method of clause 139, any other suitable clause, or any combination of suitable clauses, wherein R5is methyl. 141. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein R8is C1-C6 alkyl. 142. The method of clause 141, any other suitable clause, or any combination of suitable clauses, wherein R8is methyl. 143. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein R9is C1-C6 alkyl. 144. The method of clause 143, any other suitable clause, or any combination of suitable clauses, wherein R9is methyl. 145. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is C1-C6 alkyl. 146. The method of clause 145, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is methyl. 147. The method of clause 135, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is C1-C6alkyl. 148. The method of clause 147, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is methyl. 149. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein each of R4, R6, and R7is H. Attorney Docket No.91392-415912 150. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or halogen; each of R2, R5, R8, and R9is independently C1-C6alkyl; each of R4, R6, and R7is H; and each of R1aand R3a, when present, is independently H or halogen. 151. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or fluoro; each of R2, R5, R8, and R9is independently C1-C6alkyl; each of R4, R6, R7, is H; and each of R1aand R3a, when present, is independently H or fluoro. 152. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (IV), (V), or (VI) , , Attorney Docket No.91392-415912 , or a wherein each of R1and R3is independently H, halogen, or C1-C6alkyl; and each of R1aand R3a, when present, is independently H, halogen, or C1-C6 alkyl. 153. The method of clause 152, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound comprises at least two fluoro. 154. The method of clause 153, any other suitable clause, or any combination of suitable clauses, wherein at least two of R1, R3, and R1aand R3a, when present, are fluoro. 155. The method of clause 154, any other suitable clause, or any combination of suitable clauses, wherein 2, 3, or 4 of R1, R3, and R1aand R3a, when present, are fluoro. 156. The method of clause 155, any other suitable clause, or any combination of suitable clauses, wherein 2 of R1, R3, and R1aand R3a, when present, are fluoro. 157. The method of clause 155, any other suitable clause, or any combination of suitable clauses, wherein 3 of R1, R3, and R1aand R3a, when present, are fluoro. 158. The method of clause 152, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or halogen. 159. The method of clause 158, any other suitable clause, or any combination of suitable clauses, wherein R1is H or halogen. 160. The method of clause 159, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 161. The method of clause 159, any other suitable clause, or any combination of suitable clauses, wherein R1is halogen. 162. The method of clause 161, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 163. The method of clause 158, any other suitable clause, or any combination of suitable clauses, wherein R3is H or halogen. Attorney Docket No.91392-415912 164. The method of clause 163, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 165. The method of clause 163, any other suitable clause, or any combination of suitable clauses, wherein R3is halogen. 166. The method of clause 165, any other suitable clause, or any combination of suitable clauses, wherein R3is fluoro. 167. The method of clause 152, any other suitable clause, or any combination of suitable clauses, wherein each of R1aand R3a, when present, is independently H or halogen. 168. The method of clause 167, any other suitable clause, or any combination of suitable clauses, wherein R1ais H or halogen. 169. The method of clause 168, any other suitable clause, or any combination of suitable clauses, wherein R1ais H. 170. The method of clause 168, any other suitable clause, or any combination of suitable clauses, wherein R1ais halogen. 171. The method of clause 170, any other suitable clause, or any combination of suitable clauses, wherein R1is fluoro. 172. The method of clause 167, any other suitable clause, or any combination of suitable clauses, wherein R3ais H or halogen. 173. The method of clause 172, any other suitable clause, or any combination of suitable clauses, wherein R3ais H. 174. The method of clause 172, any other suitable clause, or any combination of suitable clauses, wherein R3ais halogen. 175. The method of clause 174, any other suitable clause, or any combination of suitable clauses, wherein R3ais fluoro. 176. The method of clause 152, any other suitable clause, or any combination of suitable clauses, wherein: each of R1and R3is independently H or halogen; and each of R1aand R3a, when present, is independently H or halogen. 177. The method of clause 152, any other suitable clause, or any combination of suitable clauses, wherein each of R1and R3is independently H or fluoro; and each of R1aand R3a, when present, is independently H or fluoro. 178. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of Attorney Docket No.91392-415912 , , 179. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of Attorney Docket No.91392-415912 , , 180. A method of preparing the fluorinated cannabinoid compound of any one of clauses 1 to 73, any other suitable clause, or any combination of suitable clauses, or a pharmaceutically acceptable salt thereof, comprising contacting a cannabinol (CBN) with a fluorinating agent to provide the fluorinated cannabinoid compound. ALTERNATIVE EMBODIMENTS Various additional embodiments of the invention are provided throughout the present disclosure. For instance, the following numbered clauses are contemplated and are non-limiting: 1. A fluorinated cannabinoid compound, wherein the fluorinated cannabinoid compound is comprised of the formula (VII) Attorney Docket No.91392-415912 , or a pharmaceutically wherein each of R1, R2, and R3is independently H or C1-C6alkyl; each of R4, R5, R6, R7, R8, and R9is independently H or C1-C6 alkyl; R10is C1-C6alkyl, C(O)-C1-C6alkyl, S(O)2-C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6 alkyl, wherein C1-C6 alkyl is optionally substituted with halogen. 2. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein R10comprises at least two fluoro. 3. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl, C(O)-C1-C6 alkyl, S(O)2-C1-C6 alkyl, and C1-C6alkyl is substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc, or a combination thereof. 4. The fluorinated cannabinoid compound of clause 3, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl, wherein C1-C6alkyl is substituted with halogen, C(O)ORa, or a combination thereof. 5. The fluorinated cannabinoid compound of clause 4, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6alkyl. 6. The fluorinated cannabinoid compound of clause 5, any other suitable clause, or any combination of suitable clauses, wherein R10is methyl. 7. The fluorinated cannabinoid compound of clause 6, any other suitable clause, or any combination of suitable clauses, wherein R10is fluoromethyl (CH2F), difluoromethyl (CF2H), or trifluoromethyl (CF3). 8. The fluorinated cannabinoid compound of clause 6, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl. Attorney Docket No.91392-415912 9. The fluorinated cannabinoid compound of clause 6, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl substituted with COOH. 10. The fluorinated cannabinoid compound of clause 6, any other suitable clause, or any combination of suitable clauses, wherein R10is trifluoromethyl. 11. The fluorinated cannabinoid compound of clause 4, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-C1-C6alkyl. 12. The fluorinated cannabinoid compound of clause 11, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl. 13. The fluorinated cannabinoid compound of clause 11, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl substituted with halogen. 14. The fluorinated cannabinoid compound of clause 11, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-CF3. 15. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein R10is selected from the group consisting of CFH2, CF2H, CF3, CF2COOH, and S(O)2-CF3. 16. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 17. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R2is C1-C6alkyl. 18. The fluorinated cannabinoid compound of clause 17, any other suitable clause, or any combination of suitable clauses, wherein R2is pentyl. 19. The fluorinated cannabinoid compound of clause 18, any other suitable clause, or any combination of suitable clauses, wherein R2is n-pentyl. 20. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 21. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R4is H. 22. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R5is C1-C6 alkyl. 23. The fluorinated cannabinoid compound of clause 22, any other suitable clause, or any combination of suitable clauses, wherein R5is methyl. 24. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R6is H. 25. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R7is H. Attorney Docket No.91392-415912 26. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R8is C1-C6 alkyl. 27. The fluorinated cannabinoid compound of clause 26, any other suitable clause, or any combination of suitable clauses, wherein R8is methyl. 28. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein R9is C1-C6alkyl. 29. The fluorinated cannabinoid compound of clause 28, any other suitable clause, or any combination of suitable clauses, wherein R9is methyl. 30. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein each of R2, R5, R8, and R9is C1-C6alkyl. 31. The fluorinated cannabinoid compound of clause 30, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is C1-C6alkyl. 32. The fluorinated cannabinoid compound of clause 31, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is methyl. 33. The fluorinated cannabinoid compound of clause 28, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is C1-C6 alkyl. 34. The fluorinated cannabinoid compound of clause 33, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is methyl. 35. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein each of R4, R6, and R7is H. 36. The fluorinated cannabinoid compound of clause 2, any other suitable clause, or any combination of suitable clauses, wherein: each of R1, R3, R4, R6, and R7is H; each of R2, R5, R8, and R9is C1-C6 alkyl; and R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl. 37. The fluorinated cannabinoid compound of clause 37, any other suitable clause, or any combination of suitable clauses, wherein: each of R1, R3, R4, R6, and R7is H; R2is pentyl; each of R5, R8and R9is methyl; and R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl. 38. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (VIII) Attorney Docket No.91392-415912 , or a wherein R10is C 1- - wherein C1-C6alkyl is optionally substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6 alkyl, wherein C1-C6 alkyl is optionally substituted with halogen. 39. The fluorinated cannabinoid compound of clause 38, any other suitable clause, or any combination of suitable clauses, wherein R10comprises at least two fluoro. 40. The fluorinated cannabinoid compound of clause 38, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl, C(O)-C1-C6 alkyl, S(O)2-C1-C6 alkyl, and C1-C6alkyl is substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc, or a combination thereof. 41. The fluorinated cannabinoid compound of clause 40, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl, wherein C1-C6alkyl is substituted with halogen, C(O)ORa, or a combination thereof. 42. The fluorinated cannabinoid compound of clause 41, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6alkyl. 43. The fluorinated cannabinoid compound of clause 42, any other suitable clause, or any combination of suitable clauses, wherein R10is methyl. 44. The fluorinated cannabinoid compound of clause 43, any other suitable clause, or any combination of suitable clauses, wherein R10is fluoromethyl, difluoromethyl, or trifluoromethyl. 45. The fluorinated cannabinoid compound of clause 43, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl. 46. The fluorinated cannabinoid compound of clause 43, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl substituted with COOH. 47. The fluorinated cannabinoid compound of clause 43, any other suitable clause, or any combination of suitable clauses, wherein R10is trifluoromethyl. Attorney Docket No.91392-415912 48. The fluorinated cannabinoid compound of clause 41, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-C1-C6 alkyl. 49. The fluorinated cannabinoid compound of clause 48, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl. 50. The fluorinated cannabinoid compound of clause 48, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl substituted with halogen. 51. The fluorinated cannabinoid compound of clause 48, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-CF3. 52. The fluorinated cannabinoid compound of clause 38, any other suitable clause, or any combination of suitable clauses, wherein R10is selected from the group consisting of CFH2, CF2H, CF3, CF2COOH, and S(O)2-CF3. 53. The fluorinated cannabinoid compound of clause 1, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of , , or 54. A pharmaceutical composition comprising a therapeutically effective amount of the fluorinated cannabinoid compound of any one of clauses 1 to 53, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or vehicles. 55. A method of treating a disease in a patient comprising administering to the patient the fluorinated cannabinoid compound of any one of clauses 1 to 53, or a pharmaceutically acceptable salt thereof. 56. The method of clause 55, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor or the CB2 receptor. Attorney Docket No.91392-415912 57. The method of clause 56, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds the CB1 receptor or the CB2 receptor. 58. The method of clause 56, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor. 59. The method of clause 56, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB2 receptor. 60. The method of clause 55, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets the CB1 receptor and the CB2 receptor. 61. The method of clause 60, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds the CB1 receptor and the CB2 receptor. 62. The method of clause 55, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a vanilloid receptor. 63. A method of treating a disease in a patient comprising administering to the patient the fluorinated cannabinoid compound of any one of clauses 1 to 53, or a pharmaceutically acceptable salt thereof, or the pharmaceutical composition of clause 54. 64. The method of clause 63, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor or a CB2 receptor. 65. The method of clause 64, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds a CB1 receptor or a CB2 receptor. 66. The method of clause 64, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor. 67. The method of clause 64, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB2 receptor. 68. The method of clause 63, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a CB1 receptor and a CB2 receptor. 69. The method of clause 68, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid binds a CB1 receptor and a CB2 receptor. 70. The method of clause 63, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid targets a vanilloid receptor. 71. A method of preparing a fluorinated cannabinoid compound comprising contacting a precursor cannabinoid compound with a fluorinating agent to provide the fluorinated cannabinoid compound. 72. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the precursor cannabinoid compound is cannabinol (CBN). Attorney Docket No.91392-415912 73. The method of clause 72, any other suitable clause, or any combination of suitable clauses, wherein the cannabinol (CBN) is of the formula , or a pharmaceutically 74. The method of combination of suitable clauses, wherein the fluorinating agent is selected from the group consisting of CFH2OTf, CFH2I, CFH2Br, CFH2SONa, CFH2SOCl, CFH2SO2Na, CFH2SO2Cl, TMSCFH2, CF2HOTf, CF2HI, CF2HBr, CF2HSONa, CF2HSOCl, CF2HSO2Na, CF2HSO2Cl, TMSCF2H, CF3OTf, CF3I, CF3Br, CF3SONa, CF3SOCl, CF3SO2Na, CF3SO2Cl, TMSCF3(CF3SiMe3), Tf2O, BrCF2COONa, 1- Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (3,3-Dimethyl-1-(trifluoromethyl)-1,2- benziodoxole), 5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate (5- (Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate), and TT-CF3+OTf−. 75. The method of clause 74, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed under basic conditions. 76. The method of clause 75, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed in the presence of a base. 77. The method of clause 76, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed in the presence of NaH, LiOH, KOH, or any combination thereof. 78. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the fluorinating agent is in molar excess to the precursor cannabinoid compound. 79. The method of clause 78, any other suitable clause, or any combination of suitable clauses, wherein the molar ratio of fluorinating agent to the precursor cannabinoid compound is of from about 1:1 to about 3:1. 80. The method of clause 79, any other suitable clause, or any combination of suitable clauses, wherein the molar ratio of fluorinating agent to the precursor cannabinoid compound is of from about 1:1 to about 2:1. 81. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed in the presence of a solvent selected from the group comprising acetone, acetonitrile, dioxane, dimethylformamide, dimethyl sulfoxide, pyridine, nitromethane, toluene, water, and any combination thereof. Attorney Docket No.91392-415912 82. The method of clause 81, any other suitable clause, or any combination of suitable clauses, wherein the solvent is acetonitrile, dioxane, toluene, water, or any combination thereof. 83. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed at a temperature of about 20 °C to about 80 °C. 84. The method of clause 83, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed at a temperature of about 20 °C to about 30 °C. 85. The method of clause 83, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed at a temperature of about 50 °C to about 70 °C. 86. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 1 hour to about 16 hours. 87. The method of clause 86, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 1 hour to about 6 hours. 88. The method of clause 87, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 3 hours to about 5 hours. 89. The method of clause 86, any other suitable clause, or any combination of suitable clauses, wherein the contacting is performed for about 10 hours to about 14 hours. 90. The method of clause 71, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (VII) , or a pharmaceutically wherein each of R1, R2, and R3is independently H or C1-C6 alkyl; each of R4, R5, R6, R7, R8, and R9is independently H or C1-C6 alkyl; R10is C1-C6alkyl, C(O)-C1-C6alkyl, S(O)2-C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6 alkyl, wherein C1-C6 alkyl is optionally substituted with halogen. Attorney Docket No.91392-415912 91. The method of clause 90, any other suitable clause, or any combination of suitable clauses, wherein R10comprises at least two fluoro. 92. The method of clause 90, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6alkyl, C(O)-C1-C6alkyl, S(O)2-C1-C6alkyl, and C1-C6alkyl is substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc, or a combination thereof. 93. The method of clause 92, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl, wherein C1-C6 alkyl is substituted with halogen, C(O)ORa, or a combination thereof. 94. The method of clause 93, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6alkyl. 95. The method of clause 94, any other suitable clause, or any combination of suitable clauses, wherein R10is methyl. 96. The method of clause 95, any other suitable clause, or any combination of suitable clauses, wherein R10is fluoromethyl, difluoromethyl, or trifluoromethyl. 97. The method of clause 95, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl. 98. The method of clause 95, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl substituted with COOH. 99. The method of clause 95, any other suitable clause, or any combination of suitable clauses, wherein R10is trifluoromethyl. 100. The method of clause 93, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-C1-C6 alkyl. 101. The method of clause 100, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl. 102. The method of clause 101, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl substituted with halogen. 103. The method of clause 101, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-CF3. 104. The method of clause 90, any other suitable clause, or any combination of suitable clauses, wherein R10is selected from the group consisting of CFH2, CF2H, CF3, CF2COOH, and S(O)2-CF3. 105. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R1is H. 106. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R2is C1-C6 alkyl. Attorney Docket No.91392-415912 107. The method of clause 106, any other suitable clause, or any combination of suitable clauses, wherein R2is pentyl. 108. The method of clause 107, any other suitable clause, or any combination of suitable clauses, wherein R2is n-pentyl. 109. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R3is H. 110. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R4is H. 111. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R5is C1-C6alkyl. 112. The method of clause 111, any other suitable clause, or any combination of suitable clauses, wherein R5is methyl. 113. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R6is H. 114. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R7is H. 115. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R8is C1-C6 alkyl. 116. The method of clause 115, any other suitable clause, or any combination of suitable clauses, wherein R8is methyl. 117. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein R9is C1-C6 alkyl. 118. The method of clause 117, any other suitable clause, or any combination of suitable clauses, wherein R9is methyl. 119. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein each of R2, R5, R8, and R9is C1-C6 alkyl. 120. The method of clause 119, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is C1-C6 alkyl. 121. The method of clause 120, any other suitable clause, or any combination of suitable clauses, wherein each of R5, R8and R9is methyl. 122. The method of clause 119, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is C1-C6alkyl. 123. The method of clause 122, any other suitable clause, or any combination of suitable clauses, wherein each of R8and R9is methyl. Attorney Docket No.91392-415912 124. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein each of R4, R6, and R7is H. 125. The method of clause 91, any other suitable clause, or any combination of suitable clauses, wherein: each of R1, R3, R4, R6, and R7is H; each of R2, R5, R8, and R9is C1-C6alkyl; and R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl. 126. The method of clause 126, any other suitable clause, or any combination of suitable clauses, wherein: each of R1, R3, R4, R6, and R7is H; R2is pentyl; each of R5, R8and R9is methyl; and R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl. 127. The method of clause 90, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is of the formula (VIII) , or a wherein R10is C1-C6alkyl, C(O)-C1-C6alkyl, S(O)2-C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc,or a combination thereof; and each of Ra, Rb, and Rcis independently H or C1-C6alkyl, wherein C1-C6alkyl is optionally substituted with halogen. 128. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein R10comprises at least two fluoro. 129. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl, C(O)-C1-C6 alkyl, S(O)2-C1-C6 alkyl, and C1-C6 alkyl is substituted with halogen, C(O)Ra, NRbRc, C(O)ORa, C(O)NRbRc, or a combination thereof. 130. The method of clause 129, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl or S(O)2-C1-C6 alkyl, wherein C1-C6 alkyl is substituted with halogen, C(O)ORa, or a combination thereof. Attorney Docket No.91392-415912 131. The method of clause 130, any other suitable clause, or any combination of suitable clauses, wherein R10is C1-C6 alkyl. 132. The method of clause 131, any other suitable clause, or any combination of suitable clauses, wherein R10is methyl. 133. The method of clause 132, any other suitable clause, or any combination of suitable clauses, wherein R10is fluoromethyl, difluoromethyl, or trifluoromethyl. 134. The method of clause 132, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl. 135. The method of clause 132, any other suitable clause, or any combination of suitable clauses, wherein R10is difluoromethyl substituted with COOH. 136. The method of clause 132, any other suitable clause, or any combination of suitable clauses, wherein R10is trifluoromethyl. 137. The method of clause 130, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-C1-C6 alkyl. 138. The method of clause 137, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl. 139. The method of clause 138, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-methyl substituted with halogen. 140. The method of clause 138, any other suitable clause, or any combination of suitable clauses, wherein R10is S(O)2-CF3. 141. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein R10is selected from the group consisting of CFH2, CF2H, CF3, CF2COOH, and S(O)2-CF3. 142. The method of clause 127, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of

[0005] Attorney Docket No.91392-415912 , or 143. The method of clause 142, any other suitable clause, or any combination of suitable clauses, wherein the fluorinated cannabinoid compound is selected from the group consisting of , , or 144. A method of preparing the fluorinated cannabinoid compound of any one of clauses 1 to 53, or a pharmaceutically acceptable salt thereof, comprising contacting a cannabinol (CBN) with a fluorinating agent to provide the fluorinated cannabinoid compound. Attorney Docket No.91392-415912 CHEMICAL SYNTHESIS Exemplary chemical entities useful in methods of the description will now be described by reference to illustrative synthetic schemes for their general preparation below and the specific examples that follow. Artisans will recognize that, to obtain the various compounds herein, starting materials may be suitably selected so that the ultimately desired substituents will be carried through the reaction scheme with or without protection as appropriate to yield the desired product. Alternatively, it may be necessary or desirable to employ, in the place of the ultimately desired substituent, a suitable group that may be carried through the reaction scheme and replaced as appropriate with the desired substituent. Furthermore, one of skill in the art will recognize that the transformations shown in the schemes below may be performed in any order that is compatible with the functionality of the particular pendant groups. Abbreviations The examples described herein use materials, including but not limited to, those described by the following abbreviations known to those skilled in the art: g grams eq equivalents Attorney Docket No.91392-415912 MeCN (ACN) acetonitrile MeOH methanol 4- ty The proposed targets can be prepared via the conventional chemistry or following the general schemes as shown below. Attorney Docket No.91392-415912 EXAMPLE 1 were purchased from commercial supplier-Sigma Aldrich / Merck and Thermo Fischer and used without purification. All reactions were performed in a round bottom flask and monitored through thin layer chromatography (TLC silica gel F254, glass plates) and analyzed using 254 nm UV light and iodine, ninhydrin stains.1H NMR,19F NMR and13C NMR spectra were recorded with a 300 MHz (1H = 300;19F = 282.5 and13C = 75 MHz) spectrometer. Chemical shift values of1H NMR were recorded in parts per million (ppm, δ) relative to tetramethylsilane (TMS, 0.00 ppm) and trichlorofluoromethane (CFCl3, 0.00ppm) in the case of19F NMR. Multiplicities are indicated as s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), coupling constants (J) were reported in Hertz (Hz) and integration value. Chemical shift values of13C NMR were recorded in parts per million (ppm, δ) and calibrated to the residual peak as an internal standard (CDCl3: δ = 77.0 ppm and DMSO: δ = 39.0 ppm). Mass spectra were obtained using the APCI+method on Advion Expression / Plate Express TLC-mass spectrometer. IR peaks were observed on infrared spectrometer (Thermo is 50 FTIR / is50 Raman and Integrating Sphere). General Procedure for the Synthesis of Compounds 1, 2, 3, 4, 5a, 5b, and 6. To a round bottom flask, were added SELECTFLUOR™ (1-(Chloromethyl)-4-fluoro- 1,4-diazabicyclo[2.2.2]octane-1,4-diium ditetrafluoroborate, FTEDA) (1.1 mmol, 2.2 equiv.) in 10 mL dry acetonitrile and let it stirred for 2 minutes to dissolve the SELECTFLUOR™ completely. Added cannabinol (CBN, 0.5 mmol, 1.0 equiv.) solution in 2-3 mL acetonitrile to the flask and continued to stir for 2 hours at room temperature resulting 94% of the crude yield with the 100% total conversion. After the TLC indicated the total consumption of starting material, the reaction mixture was allowed to cool at ambient temperature. The reaction mixture was extracted with ethyl acetate three times and the organic layer was washed with NaHCO3. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by Flash column chromatography (silica gel, hexane / Et2O) to give the desired products. Attorney Docket No.91392-415912 Large Scale Reaction: The reaction was performed on a larger scale of 16.1 mmol (5g). In a 250 mL round bottom flask, FTEDA (12.55 g, 35.4 mmol, 2.2 equiv.) solution was prepared in 90 mL of dry acetonitrile. If required, warm the solution slightly. The CBN (5 g, 16.1 mmol, 1.0 equiv.) solution in 10 mL dry acetonitrile was added in portions to the round bottom containing FTEDA solution at room temperature and continued to stir for 2 hrs at the same temperature. After the completion of reaction as monitored by TLC, the reaction mixture was extracted with ethyl acetate three times and washed with a saturated solution of NaHCO3 (60-80 mL). The combined organic layers were then dried with Na2SO4and concentrated in vacuo to give the crude product of 90% yield. (Note: the percentage yield has been calculated by taking monofluorinated product as a sole product for the theoretical yield.) Isolation method: On a 3.5cm X 8cm wide TLC (silica gel 60 F254) in a 5% diethyl ether: hexane solvent system, the reaction mixture showed a total of six spots. Spots have the following Rf values (starting from top to bottom): spot 1 (0.68), spot 2 (yellow, 0.61), spot 3 (0.55), spot 4 (dark yellow, 0.46), spot 5 (0.40), and spot 6 (0.34). Purification by Flash-silica gel (230-450 mesh size) column chromatography using 0.2- 1.5 % diethyl ether: hexanes solvent system gave spot 3 (20%) and spot 4 (30%) as a pale yellow solid and yellow oil respectively. Along with these, a mixture of spots 1, 2, 5 and 6 in 2.12 g was obtained. The separation of the mixture (spots 1, 2, 5, and 6) was performed via Preparative thin layer chromatography (prepTLC). Mixture was dissolved in methylene chloride and this solution was streak out horizontally on 20 x 20 cm UV254- silica gel GF (1500 micron) prepTLC glass plates using a capillary tube. After loading the solution of 100 mg mixture on each TLC plates, the plates were developed in 5% diethyl ether: hexane solvent system, resulting bands on the TLC plates. These bands were carefully scraped off from the TLC plates with the help of spatula and collected in the separate beakers. The scraped silica was dissolved in methylene chloride and filtered through Whatman paper. The filtrate was concentrated over vacuo to give pure products for spots 1, 2, 5 and 6. Characterization (1H NMR,19F NMR and13C NMR and Mass data) on obtained all pure spots were done to confirm the structures. The chemical structures, yield, IUPAC name for all spots / products (1, 2, 3, 4, 5 and 6) are given in Table 1 below. (Note: the percentage yield has been calculated by taking the monofluorinated product as a sole product for the theoretical / rough yield.) Attorney Docket No.91392-415912 Table 1. Spot Structure Yield (%) 1 4 Attorney Docket No.91392-415912 Spot Structure Yield (%) 5b a ac e a o o po , - uo o- , , - e y - -pe y - , - ydro-1H- benzo[c]chromen-1-one (3): Four aromatic protons between 6.1 and 8.2 ppm, while 20 aliphatic protons are present between 0.9 and 2.4 ppm. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.25 (s, 1H), 7.14 -7.12 (m, 1H), 7.03-7.06 (m, 1H), 6.11 (t, J = 1.5 Hz, 1H), 2.44 (t, J = 7.8 Hz, 2H), 2.36 (s, 3H), 1.71 (s, 6H), 1.65-1.60 (m, 2H), 1.41-1.36 (m, 4H), 0.94-0.90 (m, 3 H) ppm. In the D2O experiment, none of the peaks were suppressed or disappeared, indicating the absence of an -OH group. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.24 (s, 1H), 7.15 -7.12 (m, 1H), 7.03-7.06 (m, 1H), 6.11 (t, J = 1.5 Hz, 1H), 2.44 (t, J = 7.8 Hz, 2H), 2.36 (s, 3H), 1.70 (s, 6H), 1.65-1.60 (m, 2H), 1.41-1.36 (m, 4H), 0.94-0.92 (m, 3 H) ppm. In the IR data analysis, there was not any broad peak in the 3500-3600 cm-1range confirming the absence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=O stretch, -C=C- stretch, -C-O- stretch and -C-F stretch. The following Attorney Docket No.91392-415912 scientific information was discovered: FT-IR (neat) νmax2956, 2932. 2864, 1677, 1645, 1623, 1361, 1317, 1285, 1181, 1146, 1081, 1031, 817, cm-1. 19F-NMR showed one singlet peak at -110.24 ppm advocating the presence one or more F-atoms in the same environment. 13C-NMR showed one carbonyl peak for benzoquinone type molecules suggesting that oxidized fluorination product has been formed. The overall data is as follows: (CDCl3, 75 MHz) δ = 183.29 (t, J = 3 Hz, 1C), 156.63 (t, J = 22.5 Hz, 1C), 147.36 (t, J = 24 Hz, 1C), 137.69, 133.58, 129.62, 128.66 (t, J = 6.75 Hz, 1C), 126.62, 123.98, 122.43, 112.05, 111.60 (t, J = 3.75 Hz, 1C), 108.92, 105.80, 82.20, 31.35, 22.47, 22.29, 26.36, 22.40, 21.38, 13.95 ppm. ADVION- Unit resolution (APCI+) calcd for C21H24F2O2[M+H]+: 346.1744; observed: 347.5. This confirmed that the spot was di- fluorinated product. After combining all the information gathered, the data indicated a formation of oxidized difluorinated product (3). Characterization of Spot 4: 2,2-difluoro-6,6,9-trimethyl-3-pentyl-2,6-dihydro-1H- benzo[c]chromen-1-one (4): Four aromatic protons between 6.1 and 8.2 ppm, while 20 aliphatic protons are present between 0.9 and 2.4 ppm. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.30 (s, 1H), 7.09 -7.06 (m, 1H), 7.01-6.99 (m, 1H), 6.097-6.093 (m, 1H), 2.46-2.41 (m, 2H), 2.35 (s, 3H), 1.67 (s, 6H), 1.64-1.59 (m, 2H), 1.40-1.36 (m, 4H), 0.94-0.90 (m, 3 H) ppm. In the D2O experiment, none of the peaks were suppressed or disappeared, indicating the absence of an -OH group. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.30 (s, 1H), 7.09 -7.06 (m, 1H), 7.01-6.99 (m, 1H), 6.098 (s, 1H), 2.46-2.41 (m, 2H), 2.35 (s, 3H), 1.67 (s, 6H), 1.64-1.59 (m, 2H), 1.40-1.36 (m, 4H), 0.94-0.92 (m, 3 H) ppm. In the IR data analysis, again there was not any broad peak in the 3500-3600 cm-1range confirming the absence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=O stretch, -C=C- stretch, -C-O- stretch and -C-F stretch. The following scientific information was discovered: FT-IR (neat) νmax2958, 2927. 2860, 1673, 1586, 1564, 1400, 1188, 1136, 1042, 941, 813 cm-1. Attorney Docket No.91392-415912 19F-NMR showed one singlet peak at -108.57 ppm advocating the presence one or more F-atoms in the same environment. 13C-NMR showed one carbonyl peak for benzoquinone type molecules suggesting that oxidized fluorination product has been formed. The overall data is as follows: (CDCl3, 75 MHz) δ = 184.39 (t, J = 24 Hz, 1C), 164.18 (t, J = 2.25 Hz, 1C), 147.48 (t, J = 24 Hz, 1C), 137.85, 131.85, 128.70, 125.35, 124. 32, 123.58 (t, J = 7.5 Hz, 1C), 122.33, 107.46, 105.52 (t, J = 2.25 Hz, 1C), 104.24, 101.03, 82.76, 31.38, 29.72, 28.61, 28.35, 26.49, 22.41, 21.38, 13.95 ppm. ADVION- Unit resolution (APCI+) calcd for C21H24F2O2[M+H]+: 346.1744; observed: 347.6. This confirmed that the spot was di- fluorinated product. After combining all the information gathered, the data indicated a formation of oxidized difluorinated product (4). Distinguishing Spot 3 and Spot 4: The carbonyl peak of spot 4 is expected to have a higher coupling constant (J) since it is closer to the carbon that holds the two F-atoms. This fact was demonstrated by the spot 4 carbon NMR data (i.e., 184.39 (t, J = 24 Hz, 1C)), which distinguished the structure associated to spot 4, and in turn gave the structure of spot 3. The quaternary carbon of the ring substituted by n-pentyl has the same coupling constant in both cases (spot 3 and 4) at ~147.48ppm (t, J = 24 Hz, 1C). The same can be observed by comparing the 2D-COSY data of both spot 3 and spot 4. For the structure of spot 4, the proton para to the carbonyl expected to show correlation with the carbon holding two methyl groups. Similar results are shown by spot 4, 2D-COSY. Hence, the structure of compound 4 was confirmed for spot 4, and in turn gave the structure of compound 3 for spot 3. Characterization of Spot 5: 2-fluoro-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1- ol (5a) and 4-fluoro-6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen-1-ol (5b): ppm, while an OH-proton was observed at 5.5 ppm as a doublet. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.24 (s, 1H), 7.15 -7.07 (m, 2H), 6.35 (d, J = Attorney Docket No.91392-415912 6.6 Hz, 1H), 5.59 (d, J = 7.8 Hz, 1H), 2.59 (t, J = 7.5 Hz, 2H), 2.39 (s, 3H), 1.64-1.61 (m, 2H), 1.58 (s, 6H), 1.35-1.31 (m, 4H), 0.91-0.87 (m, 3H) ppm. In the D2O experiment, the peak at 5.5 ppm was suppressed / disappeared totally, indicating the presence of an -OH group. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.24 (s, 1H), 7.15 -7.07 (m, 2H), 6.35 (d, J = 6.6 Hz, 1H), 2.60 (t, J = 7.2 Hz, 2H), 2.39 (s, 3H), 1.64-1.61 (m, 2H), 1.58 (s, 6H), 1.35-1.33 (m, 4H), 0.91-0.87 (m, 3H) ppm. 19F-NMR showed one triplet at -156.07 ppm (t, J = 8.47 Hz, 1 or 2F) advocating the presence of either aromatic two F-atoms or one aromatic F-atom in two isomers. The latter case could be possible if the isomers are present in equal amount and same environment. ADVION- Unit resolution (APCI+) calcd. for C21H25FO2 [M+H]+: 329.1917; observed: 329.1. This confirmed that the spot was one aromatic F-atom in two isomers. In the IR data analysis, a broad peak at 3570 cm-1range confirmed the presence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=Cstretch, -C- O- stretch and -C-F stretch. The following scientific information was discovered: FTIR (neat) νmax: 3570, 2958, 2926, 2861, 1502, 1447, 1050, 910, 811, 736 cm-1. 13C-NMR data is as follows: (CDCl3, 75 MHz) δ = 149.24 (d, J = 2.2 Hz, 1C), 145.10 (d, J = 222.7 Hz, 1C), 141.0 (d, J = 17.25 Hz, 1C), 136.88, 136.70, 129.28 (d, J = 15.75 Hz, 1C), 128.14, 127.18 (d, J = 2.2 Hz, 1C), 126.97, 122.48, 109.75, 109.63 (d, J = 3.75 Hz, 1C), 77.36, 31.45, 29.41, 28.78 (d, J = 1.5 Hz, 1C), 27.12, 22.48, 21.50, 14.01 ppm. After combining all the information gathered, the data indicated a formation of a mixture of monofluorinated isomers (2- and 4- positional isomers, 5a and 5b), both in equal amount. Characterization of Spot 6: 2,4-difluoro-6,6,9-trimethyl-3-pentyl-6H- benzo[c]chromen-1-ol (6): Three aromatic protons between 7.1 and 8.3 ppm, while an OH-proton was observed at 5.3 ppm as a doublet. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.25 (s, 1H), 7.17 -7.10 (m, 2H), 5.38 (d, J = Attorney Docket No.91392-415912 7.2 Hz, 1H), 2.69 (t, J = 7.5 Hz, 2H), 2.39 (s, 3H), 1.63 (s, 6H), 1.59-1.58 (m, 2H), 1.36-1.34 (m, 4H), 0.91-0.87 (m, 3H) ppm. In the D2O experiment, the peak at 5.3 ppm was suppressed / disappeared totally, indicating the presence of an -OH group. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.25 (s, 1H), 7.16 -7.10 (m, 2H), 2.69 (t, J = 7.2 Hz, 2H), 2.39 (s, 3H), 1.63 (s, 6H), 1.59-1.58 (m, 2H), 1.36-1.34 (m, 4H), 0.91-0.87 (m, 3H) ppm. 19F-NMR showed one singlet at -150.24 ppm and one doublet at -154.15 ppm (d, J = 8.46 Hz, 1F) in 1:1 ratio, advocating the presence of two types of aromatic F-atoms present in different environments. ADVION- Unit resolution (APCI+) calcd. for C21H22F2O2[M+H]+: 347.1823; observed: 347.1. This confirmed that the spot was a difluorinated product. In the IR data analysis, a broad peak at 3567 cm-1range confirmed the presence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=Cstretch, -C- O- stretch and -C-F stretch. The following scientific information was discovered: FTIR (neat) νmax: 3567, 2961, 2930, 2863, 1506, 1457, 1112, 942, 909, 818, 733 cm-1. 13C-NMR data is as follows: (CDCl3, 75 MHz) δ = 144.37 (dd, J = 235.5, 9Hz, 1C), 143.72 (dd, J = 224.3, 8.25 Hz, 1C), 137.40 (dd, J = 12.75, 3Hz, 1C), 137.08, 136.79, 136.75 (dd, J = 18, 3.75 Hz, 1C), 128.68, 127.26, 126.54 (t, J = 3.75 Hz, 1C), 122.61, 117.84 (t, J = 20.25 Hz, 1C), 110.60, 78.11, 31.42, 29.15, 27.04, 22.85, 22.40, 21.48, 13.99 ppm. After combining all the information gathered, the data indicated a formation of difluorinated aromatic product (6). Characterization of Spot 1: 2,4,4-trifluoro-6,6,9-trimethyl-3-pentyl-4,6-dihydro-1H- benzo[c]chromen-1-one (1): Three aromatic protons between 7.0 and 8.3 ppm. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.26 (s, 1H), 7.15 (d, J = 8.1 Hz, 1H), 7.05 (d, J = 7.8 Hz, 1H), 2.47 (t, J = 7.8 Hz, 2H), 2.37 (s, 3H), 1.71 (s, 6H), 1.69-1.61 (m, 2H), 1.40-1.35 (m, 4H), 0.93-0.89 (m, 3H) ppm. Attorney Docket No.91392-415912 19F-NMR showed one doublet at -107.10 ppm (d, J = 11.3 Hz, 1F) and one triplet at -128.13 (t, J = 11.2 Hz, 1F) in 2:1 ratio, advocating the presence of two sets of F-atoms. According to the ratio, the sets should have 2F atoms in first and 1F in second set, present in different environments. ADVION- Unit resolution (APCI+) calcd. for C21H24F3O2 [M+H]+: 365.1728; observed: 365.3. This confirmed that the spot was a tri-fluorinated product. In the IR data analysis, again there was not any broad peak around 3500-3600 cm-1range confirming the absence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=O, -C=C- stretch, -C-O- stretch and -C-F stretch. The following scientific information was discovered: FT-IR (neat) νmax: 2963, 2931, 2871, 1670, 1626, 1139, 1113, 1033, 949, 817 cm-1. 13C-NMR data is as follows: (CDCl3, 75 MHz) δ = 175.64 (td, J = 24.9, 3.75Hz, 1C), 157.48- 156.84 (m, 1C), 151.09 (td, J = 264.75, 11.25 Hz, 1C), 137.95, 133.25, 129.97, 126.39, 123.30 (d, J = 2.25 Hz, 1C), 122.52, 112.60 (dd, J = 235.12, 15.75 Hz, 1C), 110.98, 109.84 (d, J = 3.75 Hz, 1C), 83.08, 31.76, 27.79 (d, J = 2.25 Hz, 1C), 27.61, 22.71, 22.27, 21.37, 13.90ppm. After combining all the information gathered, the data indicated a formation of the oxidized trifluorinated product (1). Characterization of Spot 2: 2,2,4-trifluoro-6,6,9-trimethyl-3-pentyl-2,6-dihydro-1H- benzo[c]chromen-1-one (2): Three aromatic between 7.0 and 8.3 ppm. The following scientific information was discovered:1H NMR (CDCl3, 300 MHz) δ = 8.25 (s, 1H), 7.13- 7.10 (m, 1H), 7.02 (d, J = 7.8 Hz, 1H), 2.48-2.43 (m, 2H), 2.35 (s, 3H), 1.72 (s, 6H), 1.68- 1.58 (m, 2H), 1.39-1.33 (m, 4H), 0.93-0.88 (m, 3H) ppm. 19F-NMR showed one doublet at -103.73 ppm (d, J = 14.1 Hz, 1F) and one triplet of triplet at -129.22 (tt, J = 14.1, 2.8 Hz, 1F) in 2:1 ratio, advocating the presence of two sets of F-atoms. According to the ratio, the sets should have 2F atoms in first and 1F in second set, present in different environments. Attorney Docket No.91392-415912 ADVION- Unit resolution (APCI+) calcd. for C21H24F3O2[M+H]+: 365.1728; observed: 365.3. This confirmed that the spot was a tri-fluorinated product. In the IR data analysis, again there was not any broad peak around 3500-3600 cm-1range confirming the absence of an -OH peak. In addition, there were peaks suggesting the presence of sp2C-H stretch, -C=O, -C=C- stretch, -C-O- stretch and -C-F stretch. The following scientific information was discovered: FT-IR (neat) νmax: 2958, 2934, 2869, 1680, 1583, 1384, 1366, 1036, 940, 821 cm-1. 13C-NMR data is as follows: (CDCl3, 75 MHz) δ = 183.21 (dt, J = 24.75, 1.5Hz, 1C), 157.26 (td, J = 24, 3.75 Hz, 1C), 150.34 (td, J = 261.75, 12.75 Hz, 1C), 138.14, 131.91, 129.46, 125.63, 123.62 (d, J = 3 Hz, 1C), 122.45, 106.38 (dd, J = 481.12, 15 Hz, 1C), 106.56-106.46 (m, 1C), 106.28, 83.96, 31.71, 28.26, 27.99 (d, J = 2.25 Hz, 1C), 23.38, 22.29, 21.37, 13.93ppm. After combining all the information gathered, the data indicated a formation of oxidized trifluorinated product (2). Distinguishing Spot 1 and Spot 2: In the13C-NMR data, the carbonyl peak in the structure of spot 2 in the is expected to have a higher chemical shift value due to presence of two F-atoms on the adjacent carbon, as compared to other carbonyl in the structure of spot 1. This fact is demonstrated by the spot 2 carbon NMR data (i.e. 183.21 (dt, J = 24.75, 1.5Hz, 1C)), which distinguished the structure associated to spot 2, and in turn gave the structure to spot 1. Hence, the structure of compound 2 was confirmed for spot 2, and in turn gave the structure of compound 1 for spot 1. EXAMPLE 2 10) General Methods: Unless otherwise noted, all chemicals / reagents and solvents were purchased from commercial supplier-Sigma Aldrich / Merck and Thermo Fischer and used without purification. All manipulations were conducted on the benchtop without any exclusion of air or moisture, unless otherwise noted. Reaction was conducted in 5 mL vial fitted with a Teflon-lined screw cap unless otherwise noted. HCF2OTf was prepared according to published procedure. Reaction was monitored through thin layer chromatography (TLC silica gel F254, glass Attorney Docket No.91392-415912 plates) and analyzed using 254 nm UV light and iodine, ninhydrin stains.1H NMR,19F NMR and13C NMR spectra were recorded with a 300 MHz (1H = 300;19F = 282.5 and13C = 75 MHz) spectrometer. Chemical shift values of1H NMR were recorded in parts per million (ppm, δ) relative to tetramethylsilane (TMS, 0.00 ppm) and trichlorofluoromethane (CFCl3, 0.00ppm) in the case of19F NMR. Multiplicities are indicated as s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), coupling constants (J) were reported in Hertz (Hz) and integration value. Chemical shift values of13C NMR were recorded in parts per million (ppm, δ) and calibrated to the residual peak as an internal standard (CDCl3: δ = 77.0 ppm and DMSO: δ = 39.0 ppm). Mass spectra were obtained using the APCI+method on Advion Expression / Plate Express TLC-mass spectrometer. IR peaks were observed on infrared spectrometer (Thermo is 50 FTIR / is50 Raman and Integrating Sphere). Difluorination of CBN to provide a mixture of Difluoromethyl ether (Compound 7) of Cannabinol and Cannabinol triflate (Compound 8) 1.0 equiv), acetonitrile (2.0 mL) and 6M aqueous KOH (1.0 mL). The mixture was stirred rapidly at room temperature and HCF2OTf (194 μL, 0.96 mmol, 3.0 equiv) was added at once. Note: the reactions are exothermic. The mixture was stirred vigorously for 4-5h. After the TLC indicated the total consumption of starting material, the reaction mixture was allowed to cool at ambient temperature. On a 5 cm X 10 cm TLC (silica gel 60 F254) in a 5% diethyl ether: hexane solvent system, the reaction mixture showed only one spot at 0.63 Rf. The reaction was diluted with H2O (15 mL) and extracted with ether (2 x 15 mL). The combined organic layers were dried over MgSO4, and concentrated. The crude compound (120 mg) was then purified by silica gel chromatography (silica gel, hexane / Et2O). Despite a single spot all the characterization (given below) data indicated an inseparable mixture of difluoromethyl ether of cannabinol (7) and cannabinol triflate (8) in the % ratio of 53:47 (according to19F-NMR). Characterization: difluoromethyl ether of cannabinol (7, 53% yield, 1-(difluoromethoxy)- 6,6,9- trimethyl-3-pentyl-6H-benzo[c]chromene) and cannabinol triflate (8, 47% yield, 6,6,9- trimethyl-3-pentyl-6H-benzo[c]chromen-1-yl trifluoromethanesulfonate).1H NMR (CDCl3, 300 MHz): δ = 8.07 (s, 1H), 7.84 (s, 0.59H), 7.15-7.087 (m, 3H), 6.836-6.833 (m, 1H), 6.76 (s, 0.24H), Attorney Docket No.91392-415912 6.698-6.95 (m, 1H), 6.60 (s, 1H), 6.51 (s, 0.5H), 6.26 (s, 0.25H), 2.58- 2.53 (m, 3H), 2.37 (s, 5H), 1.64-1.59 (m, 3H), 1.59 (s, 11H), 1.34-1.29 (m, 7H), 0.91-0.87 (m, 5H).19F-NMR (CDCl3, 282.5 MHz): δ = -73.51 (s, 3F), -79.68 (d, J = 73.3 Hz, 2F). ADVION- Unit resolution (APCI+) calcd. for 7, C22H27F2O2[M+H]+: 361.1979; observed: 361.2. Unit resolution (APCI+) calcd. for 8, C22H26F3O4S [M+H]+: 443.1504; observed: 443.1. FT-IR (neat) ν max: 2958, 2927, 2852, 1618, 1419, 1215, 1119, 1046, 817, 600 cm-1.13C-NMR: (CDCl3, 75 MHz) δ = 154.9, 154.7, 148.7 (t, J = 2.25 Hz, 1C), 146.0, 144.8, 144.8, 137.4, 137.3, 137.13(d, J = 2.25 Hz, 1C), 129.2, 128.4, 127.1, 126.8, 126.1, 125.1, 122.7, 122.6, 120.7, 118.0, 116.7 (t, J = 255.5 Hz, OCF2H), 116.4, 115.5, 115.4, 115.1, , 112.9, 112.8, 78.2, 77.5, 35.6, 35.5, 31.4, 31.3, 30.4, 30.3, 27.1, 26.7, 22.5, 22.4, 21.4, 21.2, 14.0, 13.9. Note: the quartet peak of the triflate group (~118 ppm with J = 320 Hz, according to literature) in Compound 8 is believed to have merged with other carbon peaks. Deprotection reaction on the mixture of Difluoromethyl ether of Cannabinol (7) and Cannabinol triflate (8) to provide the Difluoromethyl ether of CBN (7) equiv), dioxane (2.0 mL) and stirred for half a minute at room temperature. Added Et4NOH dropwise (54 μL, 0.36 mmol, 2.1 equiv.) and the mixture was stirred for 4 h at same temperature. After the indicated time frame, TLC indicated the formation of CBN back, the reaction mixture was diluted with CHCl3, washed with 1M aq. HCl, water and brine. The organic layer was dried (MgSO4) and concentrated in vacuo. The crude compound (69 mg) was then purified by silica gel chromatography (silica gel, hexane / EtOAc) resulting 42 mg of 7 and 37 mg of CBN. Characterization: (7, 42 mg yield, 1-(difluoromethoxy)-6,6,9-trimethyl-3-pentyl- 6Hbenzo[c]chromene).1H NMR (CDCl3, 300 MHz): δ = 8.07 (s, 1H), 7.15-7.09 (m, 2H), 6.76- 6.51 (m, 3H), 2.56 (t, J = 7.5 Hz, 2H), 2.38 (s, 3H), 1.67-1.62 (m, 8H), 1.34-1.30 (m, 4H), 0.89 (t, J = 6.9 Hz, 3H).19F-NMR (CDCl3, 282.5 MHz): δ= -79.68 (d, J = 76.1 Hz, 2F). ADVION- Unit resolution (APCI+) calcd. for 7, C22H27F2O2 [M+H]+: 361.1979; observed: 361.3. FT-IR (neat) νmax: 2962, 2928, 2859, 1625, 1384, 1157, 1125, 1050, 815 cm-1.13C-NMR: (CDCl3, 75 MHz) δ = 154.6, 148.7 (t, J = 2.25 Hz, 1C), 144.8, 144.7, 137.1 (d, J = 2.25 Hz, 1C), 128.4, 127.1, 126.1, 122.6, 116.7 (t, J = 255.7 Hz, OCF2H), 115.4, 113.3, 112.9, 112.8, 77.9, 35.6, 31.4, 30.4, 27.1, 22.5, 21.4, 14.0. Attorney Docket No.91392-415912 Preparation of Cannabinol triflate (8) (5 mL), 5% (w / v) , dropwise Tf2O (2.41 mmol) at a rate to maintain the reaction temperature <10℃. The reaction was allowed to warm at room temperature and stirred for 30 mins. The organic toluene layer was separated and washed with water (15 mL). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude compound (702 mg) was then purified by silica gel chromatography (silica gel, hexane / EtOAc) resulting 600 mg of 8. Characterization: (8, 600 mg (84%) yield, 6,6,9-trimethyl-3-pentyl-6H-benzo[c]chromen- 1-yl trifluoromethanesulfonate).1H NMR (CDCl3, 300 MHz): δ = 7.84 (s, 1H), 7.17-7.11 (m, 2H), 6.83 (s, 1H), 6.78 (s, 1H), 2.58 (t, J = 7.5 Hz, 2H), 2.37 (s, 3H), 1.66-1.59 (m, 8H), 1.37- 1.32 (m, 4H), 0.89 (t, J = 6.6 Hz, 3H).19F-NMR (CDCl3, 282.5 MHz): δ = -73.53 (s, 3F). ADVION- Unit resolution (APCI+) calcd. for 8, C22H26F3O4S [M+H]+: 442.1426; observed: 443.2. FT-IR (neat) νmax: 2958, 2928, 2861, 1629, 1425, 1208, 1139, 971, 819, 604 cm-1.13C- NMR: (CDCl3, 75 MHz) δ = 154.9, 146.0, 144.8, 137.4, 137.3, 129.2, 126.8, 125.1, 122.7, 118.6 (q, J = 318.8 Hz, SOCF3), 118.0, 115.5, 115.2, 78.2, 35.4, 31.3, 30.3, 26.7, 22.4, 21.2, 13.9. Preparation of O-difluoromethylated Cannabinol derivative (9) cannabinol (200 mg, 0.644 mmol, 1.0 equiv) under N2 atmosphere, 1,4-dioxane (2.0 mL) was added to dissolve the cannabinol. Then NaH (60% purity) (21 mg, 0.708 mmol, 1.1 equiv) and 1,4-dioxane (2 mL) were added with stirring at room temperature under N2. The solution was stirred at room temperature for 30 min, then BrCF2COONa (140 mg, 0.708 mmol, 1.1 equiv) and 1,4-dioxane (1 mL) were added. After the mixture was heated at 60 ℃ for 12 hours (monitor by TLC), then cooled down to room temperature and acidified with 3M HCl (aq) to pH = 1. The mixture was Attorney Docket No.91392-415912 extracted with ethyl acetate for 3 times. The combined organic phase was washed by saturated brines and dried over MgSO4. After the solution was filtered and the solvent was evaporated under vacuum, the crude product (250 mg) was purified by flash column chromatography using petroleum ether and ethyl acetate as eluent to give 94.2% yield of O-difluoromethylated cannabinol derivative, 9. Characterization: (9, 94.2% yield, 2,2-difluoro-2-((6,6,9-trimethyl-3-pentyl- 6Hbenzo[c]chromen-1-yl)oxy)acetic acid).1H NMR (CDCl3, 300 MHz): δ = 11.62 (s, 1H), 8.08 (s, 1H), 7.13-7.05 (m, 2H), 6.82 (s, 1H), 6.77 (s, 1H), 2.56 (t, J = 7.5 Hz, 2H), 2.31 (s, 3H), 1.67- 1.588 (m, 8H), 1.33-1.28 (m, 4H), 0.88 (t, J = 6.6 Hz, 3H).19F-NMR (CDCl3, 282.5 MHz): δ = - 76.14 (s, 2F). ADVION- Unit resolution (APCI+) calcd. for 9, C23H27F2O4[M+H]+: 404.1799; observed: 405.2. FT-IR (neat) νmax: 2958, 2930, 2861, 1766, 1626, 1153, 1126, 1051, 1027, 819 cm-1.13C-NMR: (CDCl3, 75 MHz) δ = 179.2, 174.6 (EtOAc), 164.0 (t, J = 42.0 Hz, 1C), 154.3, 145.9, 144.4, 137.2 (d, J = 14.25 Hz, 1C), 128.6, 127.4, 126.1, 122.4, 116.5, 116.0, 115.1, 113.8 (t, J = 270.75 Hz, 1C), 78.0, 61.9 (EtOAC), 35.6, 31.4, 30.4, 26.9, 22.5, 21.2, 14.0. Preparation of O-Trifluoromethylated Cannabinol ether (10) mmol, 5.0 equiv.), SELECTFLUOR™ (1.36g, 3.86 mmol, 2.0 equiv.), NFSI (1.21g, 3.86 mmol, 2.0 equiv.), CsF (1.76g, 11.5 mmol, 6.0 equiv.), and CBN (1.93 mmol, 1.0 equiv.) were all added one after the other in a nitrogen-filled glovebox. Next, under an Ar environment, addition of toluene (5 mL), benzotrifluoride (10.0 mL), 2-fluoropyridine (938.2 mg, 9.66 mmol, 5.0 equiv.), and CF3TMS (1.37g, 9.66 mmol, 5.0 equiv.) were made. Stirring was done with the reaction mixture at room temperature. The reaction mixture was filtered through a silica plug that had been eluted with ethanol after 10 hours. After the filtrate was concentrated in vacuo, column chromatography was used to purify the final product. Characterization: (10, 10% yield, 6,6,9-trimethyl-3-pentyl-1-(trifluoromethoxy)-6H- benzo[c]chromene).1H NMR (CDCl3, 300 MHz) δ = 7.96 (s, 1H), 7.16-7.09 (m, 2H), 6.76 (s, 2H), 2.57 (t, J = 7.5 Hz, 2H), 2.38 (s, 3H), 1.64-1.59 (m, 8H), 1.37-1.25 (m, 4H), 0.89 (t, J = 6.6 Hz, 3H).19F-NMR (CDCl3, 282.5 MHz) δ = -57.11 (s, 3F). ADVION- Unit resolution (APCI+) calcd. for 10, C22H25F3O2 [M+H]+: 378.1807; observed : 379.4. FT-IR (neat) νmax: 2962, 2926, Attorney Docket No.91392-415912 2859, 1627, 1246, 1220, 1169, 1058, 815 cm-1.13C-NMR: (CDCl3, 75 MHz) δ = 154.5, 145.9 (d, J = 1.5 Hz, 1C), 144.5, 137.2, 137.1, 128.6, 126.9, 126.0, 122.5, 120.6 (d, J = 255.7 Hz, 1C), 116.7, 115.1, 114.6, 77.7, 35.5, 31.3, 30.4, 26.9, 22.4, 21.4, 14.0.

Claims

Attorney Docket No.91392-415912 WHAT IS CLAIMED IS:

1. A compound of formula A:or alkoxy, haloalkoxy, ester, or sulfonate is optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, - C(O)ORa, or -C(O)NRbRc; each RBis independently halogen, alkyl, or haloalkyl; each of R4, R5, R6, and R7is independently H, halogen, alkyl, or haloalkyl; each of R8and R9is independently alkyl, haloalkyl, or halogen; each of Ra, Rb, and Rcis independently H, alkyl, or haloalkyl; o is 0 or 1; and m is 1, 2, 3, 4, or 5; provided that the compound comprises at least one fluoro.

2. The compound of claim 1, wherein the compound is of formula A-I, A-II, or A-III: I)Attorney Docket No.91392-415912 , , or aeach of R4, R5, R6and R7is independently H, halogen (e.g., fluoro), alkyl (e.g., C1-C6 alkyl), or haloalkyl (e.g., C1-C6 haloalkyl); each of R8and R9is independently halogen (e.g., fluoro), alkyl (e.g., C1-C6alkyl), or haloalkyl (e.g., C1-C6 haloalkyl); R10is H, alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)- haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; each RBis independently halogen (e.g., fluoro), alkyl (e.g., C1-C10 alkyl), or haloalkyl (e.g., C1-C10haloalkyl); each of Ra, Rb, and Rcis independently H, alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl); and m is 1, 2, 3, or 4.

3. The compound of claim 1 or 2, wherein the compound is of formula I, II, or III:Attorney Docket No.91392-415912 , , , or aeach of R1, R2, and R3is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl); each of R4, R5, R6, and R7is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl); each of R8and R9is independently halogen (e.g., fluoro) or alkyl (e.g., C1-C6 alkyl); and each of R1aand R3a, when present, is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl).

4. The compound of claim 1 or 2, wherein the compound is of formula VII:Attorney Docket No.91392-415912 , or a pharmaceutically each of R1, R2, and R3is; each of R4, R5, R6and R7is independently H or alkyl (e.g., C1-C6alkyl); each of R8and R9is alkyl (e.g., C1-C6 alkyl); R10is alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)- haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl is independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; and each of Ra, Rb, and Rc, when present, is independently H, alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6 haloalkyl).

5. The compound of claim 1, 2, or 3, wherein the compound is of formula IV, V, or VI: ,Attorney Docket No.91392-415912 , , or aeach of R1and R3is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6alkyl); and each of R1aand R3a, when present, is independently H, halogen (e.g., fluoro), or alkyl (e.g., C1-C6 alkyl).

6. The compound of any one of claims 1, 2, or 4, wherein the compound is of formula (VIII) , or a pharmaceuticallyR10is alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6 haloalkyl), -C(O)-alkyl, -C(O)- haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl, wherein each alkyl (e.g., C1-C6alkyl), haloalkyl (e.g., C1-C6 haloalkyl), -C(O)-alkyl, -C(O)-haloalkyl, -S(O)2-alkyl, or -S(O)2-haloalkyl isAttorney Docket No.91392-415912 independently optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc; and each of Ra, Rb, and Rc, when present, is independently H, alkyl (e.g., C1-C6 alkyl), haloalkyl (e.g., C1-C6haloalkyl).

7. The compound of claim 3 or 5, wherein each of R1and R3is independently H or halogen (e.g., fluoro).

8. The compound of any one of claims 3, 5, or 7, wherein each of R1aand R3a, when present, is independently H or halogen (e.g., fluoro).

9. The compound of any one of claims 3-8, wherein each of R1and R3is H.

10. The compound of any one of claims 3-9, wherein each of R2, R5, R8, and R9is independently C1-C6 alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl).

11. The compound of claim 10, wherein R2is pentyl (e.g., n-pentyl).

12. The compound of any one of the preceding claims, wherein each of R5, R8, and R9is methyl.

13. The compound of any one of the preceding claims, wherein each of R4, R6, and R7is H.

14. The compound of any one of claims 2, 4, or 6, wherein R10is alkyl (e.g., C1-C6alkyl), -C(O)-alkyl (e.g., -C(O)-C1-C6 alkyl), or -S(O)2-alkyl (e.g., -S(O)2-C1-C6 alkyl), wherein alkyl (e.g., C1-C6alkyl), -C(O)-alkyl (e.g., -C(O)-C1-C6alkyl), or -S(O)2-alkyl (e.g., -S(O)2-C1- C6 alkyl) is optionally substituted with one or more of halogen, -C(O)Ra, -NRbRc, -C(O)ORa, or -C(O)NRbRc.

15. The compound of any one of claims 2, 4, or 6, wherein R10is C1-C6 alkyl or C1-C6 haloalkyl, each of which is optionally substituted with -C(O)ORa(e.g., -COOH).

16. The compound of any one of claims 2, 4, or 6, wherein R10is -S(O)2-C1-C6 alkyl (e.g., -S(O)2-methyl) optionally substituted with halogen (e.g., fluoro), or -S(O)2-C1-C6 haloalkyl (e.g., -S(O)2-CF3).

17. The compound of any one of claims 2, 4, 6, or 14, wherein R10is selected from the group consisting of -CF2H, -CF3, -CF2COOH, and -S(O)2-CF3.

18. The compound of any one of the preceding claims, wherein the compound comprises at least two fluoro (e.g., 2, 3, 4, or 5 fluoro).

19. The compound of any one of the preceding claims, wherein R10comprises at least two fluoro (e.g., 2, 3, 4, or 5 fluoro).

20. The compound of claim 1 or 2, wherein the compound is selected from the group consisting ofAttorney Docket No.91392-415912 , ,21. A pharmaceutical composition comprising a therapeutically effective amount of a compound of any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable carriers or vehicles.Attorney Docket No.91392-415912 22. A method of treating a disease in a patient comprising administering to the patient in need of such treatment an effective amount of a compound of any one of claims 1 to 20, or a pharmaceutically acceptable salt thereof.

23. The method of claim 22, wherein the compound targets a CB1 receptor, a CB2 receptor, a vanilloid receptor, or a combination thereof.

24. A method of preparing a compound of any one of claims 1 to 20, comprising contacting a precursor compound with a fluorinating agent to provide the compound.

25. The method of claim 24, wherein the precursor compound is a cannabinol (CBN), and wherein the cannabinol (CBN) is of the formula , or a26. The method of claim 24 or 25, wherein the fluorinating agent is selected from the group consisting of N-fluoro-o-benzenedisulfonimide (NFOBS), N-fluorobenzenesulfonimide (NFSI), and 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (F- TEDA-BF4).

27. The method of claim 24 or 25, wherein the fluorinating agent is selected from the group consisting of CFH2OTf, CFH2I, CFH2Br, CFH2SONa, CFH2SOCl, CFH2SO2Na, CFH2SO2Cl, TMSCFH2, CF2HOTf, CF2HI, CF2HBr, CF2HSONa, CF2HSOCl, CF2HSO2Na, CF2HSO2Cl, TMSCF2H, CF3OTf, CF3I, CF3Br, CF3SONa, CF3SOCl, CF3SO2Na, CF3SO2Cl, TMSCF3 (CF3SiMe3), Tf2O, BrCF2COONa, 1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one (3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole), 5-(Trifluoromethyl)dibenzothiophenium tetrafluoroborate (5-(Trifluoromethyl)dibenzothiophenium trifluoromethanesulfonate), and TT- CF3+OTf−.

28. The method of any one of claims 24-27, wherein the fluorinating agent is in molar excess to the precursor cannabinoid compound.

29. The method of any one of claims 24-27, wherein a molar ratio of the fluorinating agent to the precursor compound is about 1:1 to about 5:1 (e.g., about 1:1 to about 3:1, or about 1:1 to about 2:1).Attorney Docket No.91392-415912 30. The method of any one of claims 24-29, wherein the contacting is performed in the presence of a solvent selected from the group comprising acetone, acetonitrile, dioxane, dimethylformamide, dimethyl sulfoxide, pyridine, nitromethane, toluene, water, and any combination thereof.

31. The method of any one of claims 24-30, wherein the contacting is performed at a temperature of about 20 °C to about 80 °C (e.g., about 20 °C to about 30 °C, or about 50 °C to about 80 °C.

32. The method of any one of claims 24-31, wherein the contacting is performed for about 1 hour to about 16 hours (e.g., about 1 hour to about 6 hours, about 3 hours to about 5 hours, or about 10 hours to about 14 hours).

33. The method of any one of claims 24-32, wherein the contacting is performed in the presence of a base selected from the group consisting of NaH, NaOH, LiOH, KOH, and any combination thereof.

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