US 20190142851A1 ( 19) United States (12 ) Patent Application Publication ( 10) Pub . No. : US 2019 /0142851 A1 CHADEAYNE (43 ) Pub. Date : May 16 , 2019 (54 ) COMPOSITIONS COMPRISING A 2017 , provisional application No. 62/ 587 , 410 , filed PSILOCYBIN DERIVATIVE AND A on Nov. 16 , 2017 , provisional application No . 62 /587 , CANNABINOID 395 , filed on Nov . 16 , 2017 . (71 ) Applicant: CaaMTech , LLC , Issaquah , WA (US ) Publication Classification (51 ) Int . Ci. ( 72 ) Inventor: Andrew R . CHADEAYNE , Issaquah , A61K 31/ 675 ( 2006 .01 ) WA (US ) A61K 31 /4045 (2006 . 01 ) A61K 31/ 4406 ( 2006 .01 ) (21 ) Appl. No. : 16 / 192, 736 A61K 31/ 05 (2006 . 01) A61K 31/ 192 (2006 .01 ) ( 22 ) Filed : Nov . 15 , 2018 A61K 31 /353 ( 2006 . 01) (52 ) U . S . CI. Related U .S . Application Data CPC ...... A61K 31/ 675 ( 2013 .01 ); A61K 31/ 4045 (60 ) Provisional application No. 62/ 613 , 360 , filed on Jan . (2013 . 01 ) ; A61K 31/ 353 (2013 .01 ) ; ACIK 3 , 2018 , provisional application No. 62 /609 , 115 , filed 31/ 05 (2013 . 01 ) ; A61K 31/ 192 (2013 . 01 ) ; on Dec . 21 , 2017 , provisional application No . 62/ 598 , A61K 31 /4406 ( 2013 . 01 ) 767, filed on Dec . 14 , 2017 , provisional application No . 62 /595 ,336 , filed on Dec . 6 , 2017 , provisional ( 57 ) ABSTRACT application No . 62 /595 , 321 , filed on Dec . 6 , 2017 , This disclosure pertains to new compositions and methods provisional application No . 62 /593 ,021 , filed on Nov . comprising a psilocybin derivative . In one embodiment, the 30 , 2017 , provisional application No . 62 / 592, 320 , compositions disclosed herein are used for a method of filed on Nov . 29 , 2017 , provisional application No . regulating a neurotransmitter receptor , e . g . , a serotonin 62/ 592 , 307 , filed on Nov. 29, 2017 , provisional appli receptor. In one embodiment, the compositions disclosed cation No . 62 /587 ,431 , filed on Nov. 16 , 2017 , pro herein comprise purified compounds, e. g ., a purified psilo visional application No. 62/ 587 ,419 , filed on Nov. 16 , cybin derivative , a purified cannabinoid , or purified terpene . US 2019 /0142851 A1 May 16 , 2019

COMPOSITIONS COMPRISING A Psilocin ( 4 -hydroxy - N , N - dimethyltryptamine ) is considered PSILOCYBIN DERIVATIVE AND A to be the second most abundant compound . Many within the CANNABINOID scientific community consider psilocin to be the only active ingredient in “ magic mushrooms, " reasoning that psilocybin CROSS REFERENCE TO OTHER RELATED serves only as a prodrug and does not have activity itself . No APPLICATIONS conclusive studies have been conducted to support or under mine this theory . [0001 ] This application claims benefit under 35 U . S . C . [0007 ] Formulated and administered correctly , psilocin 119 ( e ) to U . S . Provisional Application Nos. 62 /613 , 360 filed and psilocybin provide fast -acting and long - lasting changes Jan . 3 , 2018 ; 62/ 609 ,115 filed Dec . 21, 2017 ; 62 /598 ,767 to a person ' s mood . These effects can be accomplished with filed Dec . 14 , 2017 ; 62 / 595 , 336 filed Dec . 6 , 2017 ; 62/ 595 , only minor side effects , low potential for addiction , low 321 filed Dec . 6 , 2017 ; 62 / 593 ,021 filed Nov . 30 , 2017 ; potential for abuse , and low risk of toxicity . 62 /592 , 320 filed Nov . 29 , 2017 ; 62 /592 , 307 filed Nov. 29 , [0008 ] Currently , the state of the art for psilocybin tech 2017 ; 62 /587 , 431 filed Nov . 16 , 2017 ; 62 / 587 ,419 filed Nov . nology is not advanced . Despite a handful of studies utiliz 16 , 2017 ; 62/ 587 ,410 filed Nov . 16 , 2017 ; and 62 /587 ,395 ing purified psilocybin as a single active pharmaceutical filed Nov. 16 , 2017 , all of which are hereby incorporated by ingredient , virtually no work has been done formulating reference in their entireties . psilocybin into drug products for treating mental disorders . TECHNICAL FIELD Aside from a few studies on purified psilocybin , no efforts have been made to modulate its properties with formulating [0002 ] This disclosure relates to psilocybin technology, agents or other ingredients . No efforts have been made to which at the time of this disclosure is primarily concerned formulate particular combinations or doses of psilocybin with mycology, mushroom cultivation , crude mushroom derivatives or combinations with other active molecules . No extracts , natural mushroom preparations, fruitbody extracts , efforts have been made to formulate psilocybin into com mycelium preparations, and ( in a few cases ) the isolated positions capable of modifying activity at one or more compound psilocybin . neurotransmitter receptors . 100091. The psilocybin arts focus primarily on cultivating BACKGROUND and consuming mushrooms. Unfortunately, collecting and [0003 ] Many people worldwide are afflicted with psycho ingesting mushrooms can be dangerous because of difficul logical or mood disorders, such as depression , anxiety , ties distinguishing the desired mushroom species from simi compulsion , and post - traumatic stress disorders. Many of lar looking species . For example , mushrooms of the genus these conditions are believed to involve a person ' s serotonin Psilocybe are easily confused with toxic lookalikes. Mis system — including interactions between ( A ) the neurotrans taken identification of Psilocybe mushrooms leads to cases mitter serotonin (often abbreviated 5 -HT ) and ( B ) several of serious illness and death every year. different subtypes of serotonin neurotransmitter receptors [0010 ] Even when “magic mushrooms” are properly iden found in the human body. tified , those mushrooms vary greatly in terms of the con [0004 ] A variety of compositions are known to modulate centration of psilocybin , psilocin , and other (often over activity at the serotonin receptors . A number of pharmaceu looked ) active ingredients . Accordingly, administering a ticals ( antidepressants , serotonin reuptake inhibitors , selec specific compound or a particular dose using mushrooms is tive serotonin reuptake inhibitors, etc . ) have become avail not possible because of the variability in the chemical able . In 2014 , the Better Communication Company composition of mushrooms. projected the global market for drugs treating mental disor [0011 ] Additionally, even when “ magic mushrooms” are ders to be about $ 77 . 1 billion by 2018 and register a properly identified , they are prone to contamination . Con five - year compound annual growth rate of 2 . 3 % from 2013 tamination can result in problems, such as unwanted side to 2018 . Almost all these pharmaceuticals target neurotrans effects like “ wood lover paralysis . " mitters , e . g . , serotonergic receptors , adrenergic receptors , [0012 ] Very little work has been done with psilocybin dopaminergic receptors, etc ., and in different ways . All 10 of pharmacology because of the arts ' general understanding not the leading pharmaceutical products for treating mood dis to pursue psilocybin formulations . To the contrary , the orders ( such as depression , obsessive - compulsive disorder, current state of the art focuses almost exclusively on " magic and /or anxiety disorders ) target serotonin pathways. mushrooms. ” The highest authorities on the subject in the [ 0005 ] However, despite their unquestionable popularity United States still maintain that psilocybin has " no benefi and commercial success , the users of these pharmaceutical cial purpose ” and carries a " high potential for abuse .” products are unsatisfied with their long onset times , severe [0013 ] Until recently , very little work had been done in side -effects , and poor efficacy. In many cases , these drugs developing therapeutic methods comprising psilocybin . are harmful to the user. For example , many people taking Recent efforts have shown that taking pure isolated psilo prescription drugs targeting serotonin report feeling suicidal cybin shows promise for treating several psychological thoughts , sexual dysfunction , fatigue , elevated blood pres conditions , such as post -traumatic stress , anxiety , addiction , sure , blurred vision , abnormal heart rate , nausea , and weight depression , and compulsion . On Nov. 6 , 2017 , Newsweek gain . Magazine explained the state of the art as follows: “ Magic [ 0006 ] So - called " magic mushrooms” are taken recre mushrooms ( active psilocybin ' ) were used as an experimen ationally by millions of people in the United States . Psilo talmedical treatment in the 1960s, and some researchers are cybin ( also known as 4 - phosphoryloxy - N , N - dimethyl again looking to them for healing . For example , in a pilot tryptamine or [ 3 - ( 2 - trimethylaminoethyl ) - 1H -indol - 4 - yl] study in 2011 , mushrooms appeared to have a positive effect dihydrogen phosphate ) is considered to be the most abun on cancer patients with anxiety . In 2016 , a study demon dant psychoactive compound within a “ magic mushroom .” strated their use in treating depression .” US 2019 /0142851 A1 May 16 , 2019

[0014 ] Because psilocybin research is a relatively small ment, the methods disclosed herein comprise administering area , virtually no work has been done formulating psilocy a first dosage formulation comprising a first purified can bin or studying the pharmacology of psilocybin , its deriva nabinoid . In one embodiment, the methods disclosed herein tives , and new formulations comprising them . Properly comprise administering a first dosage formulation compris studying , formulating , and dosing psilocybin and its deriva ing a first purified terpene . In one embodiment, the methods tives would provide significant benefits in treating mood and disclosed herein comprise administering a first dosage for neurological disorders , such as depression , attention deficit mulation comprising a neurotransmitter activity modulator. hyperactivity disorder , compulsive disorder , and /or an anxi In one embodiment, the methods disclosed herein comprise ety disorder . administering a first dosage formulation comprising a first [ 0015 ] There exists a need for new compositions and purified psilocybin derivative , a first purified cannabinoid , a methods comprising one or more of 3 - ( 2 - Dimethylamino first purified terpene , and/ or a neurotransmitter activity ethyl) - 1H - indol- 4 - yl] dihydrogen phosphate , 4 - hydroxy - N , modulator. N -dimethyltryptamine , [3 - (2 - trimethylaminoethyl) - 1H -in [0022 ] In one embodiment, the methods disclosed herein dol- 4 -yl ] dihydrogen phosphate , 4 -hydroxy - N ,N ,N comprise administering the compositions disclosed herein . trimethyltryptamine, [ 3 - ( 2 -methylaminoethyl ) - 1H - indol - 4 In one embodiment, the methods disclosed herein comprise yl] dihydrogen phosphate , 4 -hydroxy - N -methyltryptamine , treating a psychological disorder, e . g ., an anxiety disorder , a [ 3 - (aminoethyl ) - 1H - indol - 4 - yl] dihydrogen phosphate , and / compulsive disorder , a depressive disorder , etc . , with the or 4 -hydroxytryptamine in a precise dosage formulation . compositions disclosed herein , e . g . , a composition with one [0016 ] There further exists a need for formulations com or more psilocybin derivatives , a composition with one or bining these formulations with othermolecules affecting the more cannabinoids , a composition with one or more ter activity of neurotransmitters . penes, and / or a combination thereof. In one embodiment, the [0017 ]. There exists a need for better methods and com methods disclosed herein comprise treating a psychological positions for targeting and / or modulating activity at one or disorder, e . g ., an anxiety disorder , a compulsive disorder, a more neurotransmitter receptors . Recently , “magic mush depressive disorder, etc. , with the compositions disclosed rooms” and one molecule contained within them have herein and a neurotransmitter activity modulator, e . g . , a shown potential application in this area . However , before serotonergic drug , a dopaminergic drug , etc . these molecules can be made into effective treatments , they [ 0023 ] Disclosed herein are new compositions comprising need to be properly studied and formulated into composi a first purified psilocybin derivative and a serotonergic drug . tions that provide consistent and specific effects , e .g ., par In one embodiment, the compositions disclosed herein com ticular activity at a neurotransmitter receptor. prise a first purified psilocybin derivative and a serotonergic [0018 ] Accordingly , the state of the art for psilocybin art drug present in purposefully engineered and unnaturally has an unmet need for formulated psilocybin compositions . occurring molar ratios . This need can be met by isolating and identifying the 10024 ] Disclosed herein are new compositions comprising molecules in magic mushrooms and studying their activity a first purified psilocybin derivative and a first purified using cellular pharmacology . cannabinoid . In one embodiment, the compositions dis closed herein comprise a first purified psilocybin derivative DETAILED DESCRIPTION and a first purified cannabinoid present in purposefully [0019 ] Disclosed herein are new methods and composi engineered and unnaturally occurring molar ratios. tions comprising a psilocybin derivative . In one embodi [0025 ] Disclosed herein are new compositions comprising ment, the compositions disclosed herein comprise one or a first purified psilocybin derivative and a first purified more psilocybin derivatives chosen from the following : terpene . In one embodiment, the compositions disclosed [ 3 - ( 2 - Dimethylaminoethyl) - 1H - indol- 4 - yl] dihydrogen herein comprise a first purified psilocybin derivative and a phosphate , 4 -hydroxytryptamine , 4 - hydroxy - N , N - dimethyl first purified terpene present in purposefully engineered and tryptamine, [ 3 - ( 2 -methylaminoethyl ) - 1H -indol - 4 - yl] dihy unnaturally occurring molar ratios. drogen phosphate , 4 -hydroxy - N -methyltryptamine , [ 3 [0026 ] Disclosed herein are new compositions comprising (aminoethyl ) - 1H -indol - 4 -yl ] dihydrogen phosphate , [ 3 -( 2 a first purified psilocybin derivative , a first purified cannabi trimethylaminoethyl) - 1H - indol -4 -yl ] dihydrogen phosphate , noid , and a first purified terpene. In one embodiment, the and 4 -hydroxy - N ,N ,N - trimethyltryptamine . compositions disclosed herein comprise a first purified psi [0020 ] In one embodiment, the compositions disclosed locybin derivative , a first purified cannabinoid , and a first herein comprise one ormore purified psilocybin derivatives purified terpene present in purposefully engineered and chosen from : [3 - (2 - Dimethylaminoethyl) - 1H -indol - 4 - yl] unnaturally occurring molar ratios . dihydrogen phosphate , 4 - hydroxytryptamine , 4 - hydroxy - N , [0027 ] Disclosed herein are new compositions comprising N - dimethyltryptamine , [ 3 - ( 2 -methylaminoethyl ) - 1H - indol a first purified psilocybin derivative , a first purified cannabi 4 - yl] dihydrogen phosphate , 4 -hydroxy - N -methyltryptam noid , and a second purified cannabinoid . In one embodi ine , [3 -( aminoethyl) - 1H - indol- 4 -yl ] dihydrogen phosphate , ment, the compositions disclosed herein comprise a first [ 3 -( 2 -trimethylaminoethyl ) - 1H -indol - 4 -yl ] dihydrogen purified psilocybin derivative , a first purified cannabinoid , phosphate , and 4 -hydroxy - N , N , N - trimethyltryptamine . and a second purified cannabinoid present in purposefully 10021] In one embodiment, the methods and compositions engineered and unnaturally occurring molar ratios. disclosed herein comprise regulating the activity of a neu 10028 ]. As used herein , the term “ chitin ” refers to a poly rotransmitter receptor with a first dosage formulation com mer found primarily in the cell walls of fungi. In one prising a first purified psilocybin derivative . In one embodi embodiment, chitin is translucent. In one embodiment, chi ment, the methods and compositions disclosed herein tin is pliable . In one embodiment , chitin is resilient . In one comprise administering a first dosage formulation compris embodiment, chitin is durable . In one embodiment, chitin ing a second purified psilocybin derivative . In one embodi- comprises nitrogen . In one embodiment, the compositions US 2019 /0142851 A1 May 16 , 2019 disclosed herein comprise between 0 - 10 mass percent of [0039 ] In one embodiment, the compounds disclosed chitin as determined by dry weight. In one embodiment, the herein are in a dried powder form , e . g ., a psilocybin deriva compositions disclosed herein comprise between 0 - 5 mass tive , a cannabinoid , a terpene , etc . percent of chitin as determined by dry weight. In one [0040 ] In one embodiment, a dried powder comprises an embodiment, the compositions disclosed herein comprise anti - clumping agent, e . g ., a desiccant. less than 1 mass percent of chitin as determined by dry [0041 ] Within the context of this disclosure , it is under weight. stood that a sample may comprise small amounts of liquid [ 0029 ] In one embodiment, the compositions disclosed that are negligible in the final measurement of a sample . In herein comprise between 0 - 15 mass percent of water as one example , it is acceptable for a composition of this determined by dry weight. In one embodiment, the compo disclosure to comprise as much as 1 % water as measured by sitions disclosed herein comprise between 0 -10 mass percent mass percent . of water as determined by dry weight. In one embodiment, [0042 ] As used herein , the term “ mass percent ” , aka the compositions disclosed herein comprise between 0 - 5 " percent by mass ” , “mass % ” , etc ., refers to the amount of mass percent of water as determined by dry weight. In one a compound relative to the entire mass of a sample as a embodiment, the compositions disclosed herein comprise fraction of 100 . In one embodiment, mass percent is calcu between 0 - 1 mass percent of water as determined by dry lated with the following formula for a compound of interest : weight. (mass of compound of interest in grams) / ( totalmass (0030 ] As used herein , the term “ protein ” refers to a large of composition in grams) x100 % molecule comprising one or more amino acid chains (poly peptides ) . In one embodiment, a protein performs a function [0043 ] In one example , a composition weighs 100 g and within an organism , e . g . , catalysing metabolic reactions , comprises 0 . 5 g of a first purified psilocybin derivative , 8 g facilitating DNA replication , responding to stimuli, trans of a first purified cannabinoid , and 2 .5 g of a first purified porting molecules , etc . In one embodiment, a protein serves terpene . The mass percent of the first purified psilocybin as a structural component in an organism . derivative, the first purified cannabinoid , and the first puri [0031 ] In one embodiment, the compositions disclosed fied terpene are 0 . 5 % , 8 % , and 2 . 5 % respectively . herein comprise between 0 - 15 mass percent of protein as [0044 ] In one example, for a 25 g composition comprising determined by dry weight. In one embodiment, the compo 2 g of a psilocybin derivative . The amount of a psilocybin sitions disclosed herein comprise between 0 - 10 mass percent derivative within a composition is determined by the fol of protein as determined by dry weight. In one embodiment, lowing : the compositions disclosed herein comprise between 0 - 5 2 . 0 g of psilocybin derivative : 25 . 0 g of composi mass percent of protein as determined by dry weight. In one tionx100 % = 8 .0 % embodiment, the compositions disclosed herein comprise [0045 ]. Within the context of this disclosure , the term between 0 - 1 mass percent of protein as determined by dry “ purified ” means separated from other materials , such as weight. In one embodiment, the compositions disclosed plant or fungal material, e . g ., protein , chitin , cellulose , or herein comprise less than 5 mass percent of protein as water . In one embodiment, the term “ purified ” refers to a determined by dry weight. compound substantially free of other materials . In one [0032 ] As used herein , the term “ dry weight” refers to a embodiment, the term “ purified ” refers to a compound that measurement of the mass of a sample after removing all , or is substantially free from a second tryptamine compound . In substantially all, the liquid from the sample . In one embodi one embodiment, the term “ purified ” refers to a compound ment, removing liquid comprises dehydrating, heating , stir substantially free from histidine . In one embodiment, the ring , filtering, and / or any other method suitable for liquid term “ purified ” refers to a compound substantially free from water . In one embodiment, dry weight is measured by a biological material, such as mold , fungus, plant mater, or pounds . In one embodiment, dry weight is measured by bacteria . In one embodiment, the term “ purified ” refers to a ounces . In one embodiment, dry weight is measured by compound substantially free from a paralytic . grams, e . g . , milligrams, kilograms, etc . [0046 ] In one embodiment, the term “ purified ” refers to a [0033 ] In one embodiment, the compositions disclosed compound which has been separated from other compounds herein are in the form of a dried powder . that are typically co -extracted when the purified compound [ 0034 ] As used herein , the term “ dried powder ” refers to is extracted from a naturally occurring organism . In one a substance composed of fine particles and comprising little embodiment, a “ purified ” psilocybin derivative is partially or no liquid material. In one embodiment, a dried powder is or completely isolated from other psilocybin derivatives derived by evaporating alcohol from a solution leaving present in a source material, such as a psilocybin - containing behind dried particles . In one embodiment, a dried powder mushroom . In one example , " purified ” baeocystin is sub is a precipitate from a solution . In one embodiment, a dried stantially free from psilocybin and/ or psilocin . By contrast , powder is a solid collected from a plant ( e . g ., mushrooms) traditional psilocybin mushroom extracts ( aka crude extracts and pulverized into a powder, e . g . , using a mortar and pestle . or fruit body extracts ) would be expected to contain an [0035 ] In one embodiment, a dried powder is composed of unpredictable and varying amount of psilocybin , psilocin , particles with a crystalline structure . baeocystin , norbaeocystin , salts thereof, or combinations [ 0036 ] In one embodiment, a dried powder is composed of thereof. Other examples of unpurified psilocybin derivatives pure crystals. would include mycelium containing psilocybin derivatives [0037 ] In one embodiment, a dried powder is composed of and / or naturally occurring fungal material such as biological a mixture of crystals . material and/ or structural material such as chitin . Similarly , [0038 ] Within the context of this disclosure , any method the term “ cannabis extracts ” or “ cannabinoid extracts” tra for removing liquid is suitable for making a dried powder, ditionally refers to whole plant ( aka crude or full spectrum e .g ., heating , mixing , filtering, evaporating , etc . extracts ) which have not been subjected to further purifica US 2019 /0142851 A1 May 16 , 2019

tion to eliminated unwanted molecules that naturally occur indicate that the presence and amounts of psychoactive in the cannabis plant. For example , a “ cannabis extract compounds within naturally occurring samples is considered comprising cannabidiol” could be expected to include can to be highly variable . nabidiol (aka “ CBD ” ) and also varying amounts of other [0061 ] Disclosed herein are new compositions comprising compounds, including cannabinoids, terpenes , and other particular ratios of [ 3 - ( 2 - Dimethylaminoethyl) - 1H - indol -4 biological material. yl] dihydrogen phosphate , 4 -hydroxy -N ,N - dimethyl [ 0047 ] In one embodiment, the term “ purified ” refers to a tryptamine , [3 -( 2 - trimethylaminoethyl) - 1H -indol - 4 -yl ] compound or composition that has been crystallized . dihydrogen phosphate , 4 -hydroxy - N , N , N -trimethyltryptam [ 0048 ] In one embodiment, the term “ purified ” refers to a ine , [ 3 -( 2 -methylaminoethyl ) - 1H - indol- 4 - yl] dihydrogen compound or composition that has been chromatographed , phosphate , 4 -hydroxy - N -methyltryptamine , [ 3 - amino for example by gas chromatography , liquid chromatography ethyl) - 1H - indol -4 -yl ] dihydrogen phosphate, and /or 4 -hy ( e. g ., LC , HPLC , etc .) , etc . droxytryptamine ; and their salts and derivatives. [ 0049 ] In one embodiment , the term “ purified ” refers to a [0062 ] As used herein , the term “ particular ratio ” refers to compound or composition that has been distilled . the amount of a compound in relation to the amount of [0050 ] In one embodiment, the term “ purified ” refers to a another compound or compounds. In one embodiment, there compound or composition that has been sublimed . is an about 1 : 1 ratio of [ 3 - ( 2 -Dimethylaminoethyl ) -1H [0051 ] In one embodiment, the term “ purified ” refers to a indol- 4 - yl] dihydrogen phosphate to 4 -hydroxy - N , N - dim compound or composition that has been subject to two or ethyltryptamine . In one embodiment, a particular ratio of more steps chosen from crystallization , chromatography, compounds is measured by the same unit , e . g . , grams, distillation , or sublimation . kilograms, pounds, ounces, etc . In one embodiment, a par [0052 ] In one embodiment, the term “ purified ” refers to a ticular ratio of compounds is measured in moles , i . e . , molar compound that is between 80 - 100 % pure , meaning that the proportions or molar ratios. compound makes up 80 - 100 % of the total mass of the [0063 ] In one example , there is a particular ratio of 1 composition . kilogram to 2 grams of [ 3 - ( 2 - Dimethylaminoethyl) - 1H - in [ 0053] In one embodiment, the term “ purified ” refers to a dol -4 -yl ] dihydrogen phosphate to 4 -hydroxy - N , N - dimeth compound that is between 90 - 100 % pure , meaning that the yltryptamine . compound makes up 90 - 100 % of the total mass of the [ 0064 ] Disclosed herein are new compositions comprising composition . particular amounts of [ 3 - ( 2 -Dimethylaminoethyl ) - 1H - indol [0054 ] In one embodiment, the term “ purified ” refers to a 4 - yl] dihydrogen phosphate , 4 - hydroxy- N , N - dimethyl compound that is between 95 - 100 % pure , meaning that the tryptamine , [3 -( 2 -trimethylaminoethyl ) - 1H -indol - 4 -yl ] compound makes up 95 - 100 % of the total mass of the dihydrogen phosphate , 4 - hydroxy - N , N , N - trimethyltryptam composition . ine , [ 3 - ( 2 -methylaminoethyl ) - 1H - indol- 4 -yl ] dihydrogen [ 0055 ] In one embodiment, the term “ purified ” refers to a phosphate , 4 -hydroxy - N -methyltryptamine , [ 3 -( amino compound that is between 99 - 100 % pure , meaning that the ethyl) - 1H - indol - 4 - yl] dihydrogen phosphate , and / or 4 -hy compound makes up 99 - 100 % of the total mass of the droxytryptamine ; and their salts and derivatives. composition . [ 0065 ] As used herein , the term “ particular amount” refers 10056 ] In one embodiment, the term “ purified ” refers to a to the quantity of a compound or compounds. In one compound that is between 99 . 9 - 100 % pure, meaning that the embodiment, a particular amount is the combined quantity compound makes up 99 . 9 - 100 % of the total mass of the of two compounds within a sample . In one embodiment, a composition . particular amount is measured by dry weight. In one [0057 ] Additionally , the compounds disclosed herein are embodiment, the particular amount has 1 , 2 , 3 , or 4 signifi often found in so - called “ conjugated ” or “ derivatized ” forms cant figures . during chemical analysis . In one example , a psilocybin [ 0066 ] Disclosed herein are new compositions comprising derivative is in the form of a glucuronide derivative in little or no deviation (between samples of the said compo human serum assays . Enzymatic hydrolysis converts the sitions ) of one or more of the following molecules : [ 3 - ( 2 glucuronide derivative into a non - glucuronide form . Prior to Dimethylaminoethyl) - 1H - indol- 4 - yl] dihydrogen phos extraction , hydrolysis of the glucuronide derivative can be phate , 4 -hydroxy - N , N - dimethyltryptamine, [ 3 - ( 2 useful. trimethylaminoethyl) - 1H - indol- 4 - yl] dihydrogen phosphate , [0058 ] For example , one can deduce the concentration of 4 -hydroxy - N , N ,N - trimethyltryptamine , [3 - ( 2 -methylamino psilocin by GC /MS by using beta - glucuronidase for liber ethyl) - 1H - indol- 4 -yl ] dihydrogen phosphate, 4 -hydroxy - N ating psilocin from its conjugated (aka glucuronide deriva methyltryptamine , [ 3 - ( aminoethyl) - 1H -indol -4 - yl] dihydro tive form ) in urine and then using MSTFA ( N -methyl - N gen phosphate , and / or 4 - hydroxytryptamine; and their salts trimethylsilyltrifluoroacetamide ) for derivatization of and derivatives . psilocin to its trimethylsilyl derivative . [0067 ] Disclosed herein is a new composition , compris [0059 ] GC /MS can be used for identification and quanti ing : fication of psilocin in biological specimens. [ 0068 ] a first purified psilocybin derivative ; wherein the [ 0060 ] Psilocin and psilocybin can also be identified by first purified psilocybin derivative is chosen from [ 3 using liquid chromatography with or without tandem mass ( 2 - Dimethylaminoethyl) - 1H - indol - 4 - yl] dihydrogen spectrometry ( LC /MS /MS ) . When using LC /MS , method phosphate , 4 -hydroxy - N , N - dimethyltryptamine , [ 3 - ( 2 derivatization prior to analysis is often not required . Liquid methylaminoethyl) - 1H - indol- 4 - yl] dihydrogen phos chromatography combined with tandem mass spectrometry phate , 4 -hydroxy - N -methyltryptamine , [ 3 - (amino for analysis of psilocin and psilocybin in psychoactive ethyl) - 1H - indol- 4 - yl] dihydrogen phosphate , mushrooms may also provide useful samples . All data 4 -hydroxytryptamine , [ 3 - ( 2 - trimethylaminoethyl) - 1H US 2019 /0142851 A1 May 16 , 2019

indol- 4 - yl] dihydrogen phosphate , and 4 -hydroxy - N , N , [0083 ] In one embodiment, a psilocybin derivative within N - trimethyltryptamine ; and the compositions disclosed herein is a compound defined by [0069 ] a second purified psilocybin derivative ; wherein the following structural formula A : the second purified psilocybin derivative is chosen from [ 3 - ( 2 - Dimethylaminoethyl) - 1H - indol- 4 - yl] dihy drogen phosphate , 4 -hydroxy - N , N - dimethyltryptam Ri, R2 ine , [ 3 - ( 2 -methylaminoethyl ) - 1H - indol- 4 - yl] dihydro gen phosphate , 4 -hydroxy - N -methyltryptamine , [ 3 ( aminoethyl) - 1H - indol- 4 - yl] dihydrogen phosphate , RS 4 - hydroxytryptamine , [ 3 - ( 2 - trimethylaminoethyl) - 1H Ron indol - 4 - yl] dihydrogen phosphate , and 4 -hydroxy - N , N , N - trimethyltryptamine . [0070 ] In one embodiment, the compositions disclosed herein comprise a molar ratio between about 10 : 1 to about 1 : 10 of the first purified psilocybin derivative to the second KS purified psilocybin derivative . [0071 ] In one embodiment, the compositions disclosed wherein each of R1, R2, Rz , R4, R5, R . , R7, Rg, Ry, and Rio herein comprise a molar ratio between about 100 : 1 to about is chosen from an electron pair , a hydrogen , an alkyl, an 1 : 100 of the first purified psilocybin derivative to the second alkenyl, an alkynyl, a phenyl , a halide, a hydroxyl, a purified psilocybin derivative . carbonyl, an aldehyde , a haloformyl, a carbonate ester , a [ 0072 ] In one embodiment, the compositions disclosed carboxylate , a carboxyl, an ester , a hydroperoxy , a peroxy, herein comprise a molar ratio between about 1 , 000 : 1 to an ether, a hemiacetal, a hemiketal, an acetal, a ketal, an about 1 : 1 , 000 of the first purified psilocybin derivative to the orthoester, a methylenedioxy , an orthocarbonate ester, car second purified psilocybin derivative . boxamide, an amine, an imine , an amide, an azide , an azo , [0073 ] In one embodiment, the compositions disclosed a cyanate , a nitrate , a nitrile , an isonitrile , a nitrosooxy, a herein comprise a molar ratio of about 10 ,000 : 1 to about nitro , a pyridyl, a thiol, a sulfide , sulfinyl, a sulfonyl, a 1 : 10 ,000 of the first purified psilocybin derivative to the thiocyanate , a carbonothioyl, or a phosphate . second purified psilocybin derivative . [0084 ] In one embodiment, a psilocybin derivative is a 10074 ] In one embodiment, the first purified psilocybin compound defined by the structural formula A , wherein each derivative is [ 3- (2 -Dimethylaminoethyl ) -1H - indol- 4 -yl ] of R1, R2, and Rz is independently chosen from an electron dihydrogen phosphate . pair , a hydrogen , or an alkyl ; wherein R4 is hydrogen ; [ 0075 ] In one embodiment, the first purified psilocybin wherein R , is chosen from a hydroxyl, an ether, or a derivative is 4 -hydroxy - N , N - dimethyltryptamine . phosphate ; and wherein each of Ro R7, R8, R9, and Rio is [0076 ] In one embodiment, the first purified psilocybin hydrogen . derivative is [ 3 - ( 2 -methylaminoethyl ) - 1H -indol - 4 - yl] dihy [0085 ] In one embodiment, a psilocybin derivative is a drogen phosphate . compound defined by the structural formula A , wherein each [0077 ] In one embodiment, the first purified psilocybin of R , R . , and R , is independently chosen from an electron derivative is 4 -hydroxy - N -methyltryptamine . pair , a hydrogen , or an alkyl; wherein each of R and R , is 10078 ] In one embodiment, the first purified psilocybin hydrogen ; wherein R , is chosen from a hydroxyl, an ether, derivative is [ 3 - ( aminoethyl ) - 1H - indol - 4 - yl ] dihydrogen or a phosphate ; and wherein each of R7, R8, R9, and R10 is phosphate . hydrogen . [0079 ] In one embodiment, the first purified psilocybin [ 0086 ] In one embodiment , a “ first psilocybin derivative” derivative is 4 -hydroxytryptamine . is [ 3 - ( 2 - Dimethylaminoethyl) - 1H -indol - 4 -yl ] dihydrogen [0080 ] In one embodiment, the first purified psilocybin phosphate . derivative is [3 - (2 - trimethylaminoethyl) -1H -indol - 4- yl] 10087 ] As used herein , the term “ 53 - ( 2 - Dimethylamino dihydrogen phosphate . ethyl) - 1H - indol- 4 -yl ] dihydrogen phosphate ” refers to a [0081 ] In one embodiment, the first purified psilocybin compound , and / or salts thereof , with the following structural derivative is 4 -hydroxy - N , N , N -trimethyltryptamine . formula : [0082 ] As used herein , the term “ psilocybin derivative” refers to a compound having a core structure similar to the compound [ 3 - ( 2 - Dimethylaminoethyl) - 1H - indol- 4 -yl ] dihy H . drogen phosphate , aka “ psilocybin ” . In one embodiment, a - O psilocybin derivative is dephosphorylated , such as a phenol OH or derivative thereof. In one embodiment, a psilocybin derivative comprises zero , one , two, or three alkyl groups O= covalently bonded to the nitrogen atom on the aminoethyl group . In one embodiment, a psilocybin derivative com prises an amine ( NH , ) group . In one embodiment, a psilocybin derivative comprises a hydroxyl ( OH ) group . In one embodiment, a psilocybin derivative comprises a carbonyl group . In one embodiment, a psilocybin derivative comprises an ester group . In one embodiment , a psilocybin derivative comprises a carboxyl group . In one embodiment, [0088 ] [ 3 - ( 2 -Dimethylaminoethyl ) - 1H - indol- 4 - yl] dihy a psilocybin derivative comprises an amide group . drogen phosphate is often described by the name " psilocy US 2019 /0142851 A1 May 16 , 2019 bin ” . Psilocybin is a psychoactive prodrug often found in [0096 ] As used herein , the term “ 4 -hydroxy - N , N , N - trim mushrooms of genus Psilocybe. See American Chemical ethyltryptamine ” refers to a compound , and /or salts thereof, Society , Molecule of the Week ( Oct . 2 , 2017 ). When with the following structural formula : ingested , psilocybin is converted into psilocin through chemical and / or biological processes in the human body. Id . Within the context of this disclosure, unless otherwise specified , [ 3 - ( 2 - Dimethylaminoethyl) - 1H - indol - 4 - yl] dihy drogen phosphate may be present in its protonated or OH deprotonated (salt or freebase ) forms or mixtures thereof depending on the context, for example , the pH of the solution or composition . [0089 ] In one embodiment, a “ first psilocybin derivative” is 4 -hydroxy - N , N -dimethyltryptamine . [ 0090 ] As used herein , the term “ 4 -hydroxy - N , N - dimeth yltryptamine” refers to a compound , and / or salts thereof, with the following structural formula : 100971. Within the context of this disclosure , unless other wise specified , 4 - hydroxy - N , N , N -trimethyltryptamine may be present in its protonated or deprotonated (salt or freebase ) forms or mixtures thereof depending on the context, for example , the pH of the solution or composition . [0098 ] In one embodiment, a “ first psilocybin derivative” is [ 3 - ( 2 -methylaminoethyl ) - 1H - indol- 4 - yl] dihydrogen phosphate . 100991. As used herein , the term “ 3 - ( 2 -methylamino ethyl) - 1H - indol- 4 -yl ] dihydrogen phosphate ” refers to a compound , and /or salts thereof, with the following structural formula :

H [0091 ] 4 -hydroxy - N , N -dimethyltryptamine is also known by the name “ psilocin ” . Within the context of this disclosure , ?? unless otherwise specified , 4 -hydroxy -N , N -dimethyl tryptamine may be present in its protonated or deprotonated OS ( salt or freebase ) forms or mixtures thereofdepending on the context, for example , the pH of the solution or composition . [0092 ] In one embodiment, a “ first psilocybin derivative” is [ 3 -( 2- trimethylaminoethyl) - 1H -indol -4 - yl ] dihydrogen phosphate . [0093 ] As used herein , the term “ [ 3 -( 2 -trimethylamino ethyl) - 1H - indol- 4 -yl ] dihydrogen phosphate ” refers to a 10100 ] Within the context of this disclosure , unless other compound , and /or salts thereof, with the following structural wise specified , [ 3 - ( 2 -methylaminoethyl ) - 1H - indol- 4 - yl ] formula : dihydrogen phosphate may be present in its protonated or deprotonated (salt or freebase ) forms or mixtures thereof depending on the context, for example , the pH of the solution or composition . ON [0101 ] In one embodiment, a “ first psilocybin derivative” O= is 4 -hydroxy - N -methyltryptamine . 0102 ]. As used herein , the term “ 4 -hydroxy - N -methyl tryptamine ” refers to a compound , and /or salts thereof, with the following structural formula :

OH 10094 ). Within the context of this disclosure , unless other wise specified, [ 3 - ( 2 - trimethylaminoethyl) - 1H - indol- 4 - yl] dihydrogen phosphate may be present in its protonated or deprotonated (salt or freebase ) forms or mixtures thereof depending on the context, for example, the pH of the solution or composition . [0095 ] In one embodiment, a “ first psilocybin derivative” is 4 -hydroxy - N ,N , N -trimethyltryptamine . US 2019 /0142851 A1 May 16 , 2019

[0103 ] Within the context of this disclosure , unless other noid is derived from a plant, e . g ., a plant of genus cannabis , wise specified , 4 -hydroxy - N -methyltryptamine may be pres i. e . , a phytocannabinoid . In one embodiment, the cannabi ent in its protonated or deprotonated ( salt or freebase ) forms noid is artificially made in a lab , i. e ., a synthetic cannabi or mixtures thereof depending on the context, for example , noid . Many cannabinoids can be identified by the “ cannabi” the pH of the solution or composition . text in their chemical name. There are at least 113 different [0104 ] In one embodiment, a “ first psilocybin derivative” cannabinoids isolated from cannabis , exhibiting varied is [ 3 - ( aminoethyl) - 1H - indol- 4 - yl ] dihydrogen phosphate . ( similar and different) effects . [0105 ] As used herein , the term “ [ 3 - ( aminoethyl) - 1H [0113 ] Examples of cannabinoids within the context of indol- 4 - yl] dihydrogen phosphate ” refers to a compound , this disclosure include the following molecules: Cannabi and /or salts thereof, with the following structural formula : chromene (CBC ) , Cannabichromenic acid (CBCA ) , Can nabichromevarin (CBCV ), Cannabichromevarinic acid (CB CVA ) , Cannabicyclol (CBL ) , Cannabicyclolic acid (CBLA ) , HH Cannabicyclovarin (CBLV ) , Cannabidiol (CBD ) , Canna N bidiol monomethylether (CBDM ) , Cannabidiolic acid OH 1 H. (CBDA ) , Cannabidiorcol (CBD -C1 ) , Cannabidivarin ( CBDV ) , Cannabidivarinic acid (CBDVA ) , Cannabielsoic acid B (CBEA - B ) , Cannabielsoin (CBE ) , Cannabielsoin acid A (CBEA - A ), Cannabigerol ( CBG ), Cannabigerol monomethylether (CBGM ) , Cannabigerolic acid (CBGA ) , Cannabigerolic acid monomethylether (CBGAM ) , Cannab igerovarin (CBGV ) , Cannabigerovarinic acid (CBGVA ), Cannabinodiol (CBND ) , Cannabinodivarin (CBDV ) , Can ] nabinol (CBN ) , Cannabinol methylether (CBNM ), Cannabi nol- C2 ( CBN - C2 ) , Cannabinol- C4 (CBN - C4 ), Cannabinolic 10106 ]. Within the context of this disclosure , unless other acid (CBNA ), Cannabiorcool (CBN -C1 ) , Cannabivarin wise specified , [ 3 - ( aminoethyl) - 1H - indol- 4 - yl] dihydrogen (CBV ) , Cannabitriol (CBT ) , Cannabitriolvarin (CBTV ) , phosphate may be present in its protonated or deprotonated 10 - Ethoxy - 9 - hydroxy - delta -ba - tetrahydrocannabinol, Cann ( salt or freebase ) forms or mixtures thereof depending on the bicitran (CBT ) , Cannabiripsol ( CBR ) , 8 , 9 - Dihydroxy -delta context, for example , the pH of the solution or composition . 6a - tetrahydrocannabinol , Delta - 8 - tetrahydrocannabinol [0107 ] In one embodiment, a “ first psilocybin derivative ” (18 - THC ), Delta -8 - tetrahydrocannabinolic acid ( 48 is 4 -hydroxytryptamine . THCA ) , Delta - 9 - tetrahydrocannabinol ( THC ) , Delta - 9 -tet [0108 ] As used herein , the term “ 4 -hydroxytryptamine ” rahydrocannabinol- C4 ( THC -C4 ), Delta - 9 - tetrahydrocan refers to a compound , and /or salts thereof, with the follow nabinolic acid A ( THCA - A ) , Delta - 9 ing structural formula : tetrahydrocannabinolic acid B ( THCA - B ), Delta -9 tetrahydrocannabinolic acid - C4 ( THCA - C4 ) , Delta - 9 tetrahydrocannabiorcol ( THC -C1 ) , Delta - 9 H H . tetrahydrocannabiorcolic acid ( THCA - C1 ), Delta - 9 tetrahydrocannabivarin ( THCV ) , Delta - 9 tetrahydrocannabivarinic acid ( THCVA ), 10 -Oxo - delta -6a OH tetrahydrocannabinol (OTHC ), Cannabichromanon (CBCF ) , Cannabifuran (CBF ) , Cannabiglendol, Delta - 9 - cis tetrahydrocannabinol ( cis - THC ) , Tryhydroxy - delta - 9 - tetra hydrocannabinol ( triOH - THC ) , Dehydrocannabifuran (DCBF ) , and 3 , 4 , 5 ,6 - Tetrahydro - 7 -hydroxy - alpha - alpha - 2 trimethyl- 9 -n -propyl - 2 ,6 -methano -2H - 1 -benzoxocin -5 methanol . 0114 ] In one embodiment, the term “ cannabinoid ” refers [0109 ] Within the context of this disclosure , unless other to a compound chosen from THC , THCA , THCV , THCVA , wise specified , 4 - hydroxytryptamine may be present in its CBC , CBCA , CBCV, CBCVA , CBD , CBDA , CBDV , protonated or deprotonated ( salt or freebase ) forms or mix CBDVA , CBG , CBGA , CBGV , or CBGVA . tures thereof depending on the context, for example , the pH [0115 ] As used herein , the term “ THC ” , or tetrahydrocan of the solution or composition . nabinol, refers to a compound with the following structural [0110 ] As used herein , the term “ salt ” refers to a neutral formula : ized ionic compound . In one embodiment, a salt is formed from the neutralization of acids and bases . In one embodi ment, a salt is electrically neutral. [ 0111 ] In one embodiment, the compositions and methods disclosed herein comprise administering a first cannabinoid . OH In one embodiment, a first cannabinoid is a first purified cannabinoid . [0112 ] As used herein , the term “ cannabinoid ” refers to a compound from a class of molecules commonly found in plants of the genus cannabis and their derivatives . In one embodiment, the cannabinoid is endogenous to an animal, i. e ., an endocannabinoid . In one embodiment, the cannabi US 2019 /0142851 A1 May 16 , 2019

[0116 ] Within the context of this disclosure , the term [0121 ] As used herein , the term “ THCVA ” refers to a “ THC ” comprises any derivative and /or salt thereof. In one compound with the following structural formula : embodiment, the compositions and methods disclosed herein comprise administering a formulation of THC and a first psilocybin derivative . In one embodiment, the compo sitions and methods disclosed herein comprise administer ing purified THC and a first psilocybin derivative . In one OH O embodiment, the compositions and methods disclosed herein comprise administering THC and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri fied THC and a first purified psilocybin derivative . [0117 ] As used herein , the term “ THCA” refers to a compound with the following structural formula : [0122 ] Within the context of this disclosure , the term “ THCVA ” comprises any derivative and /or salt thereof. In one embodiment , the compositions and methods disclosed herein comprise administering a formulation of THCVA and a first psilocybin derivative . In one embodiment, the com OH O positions and methods disclosed herein comprise adminis tering purified THCVA and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed LOH herein comprise administering THCVA and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri fied THCVA and a first purified psilocybin derivative . [0123 ] As used herein , the term “ CBC ” refers to a com [ 0118 ] Within the context of this disclosure , the term pound with the following structural formula : “ THCA ” comprises any derivative and /or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of THCA and a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified THCA and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering THCA and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri HO fied THCA and a first purified psilocybin derivative . [0124 ] Within the context of this disclosure , the term 0119 ]. As used herein , the term “ THCV ” refers to a “ CBC ” comprises any derivative and /or salt thereof. In one compound with the following structural formula : embodiment , the compositions and methods disclosed herein comprise administering a formulation of CBC and a first psilocybin derivative . In one embodiment, the compo sitions and methods disclosed herein comprise administer ing purified CBC and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering CBC and a first purified psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering puri fied CBC and a first purified psilocybin derivative . [0125 ] As used herein , the term “ CBCA ” refers to a compound with the following structural formula : [ 0120 ] Within the context of this disclosure , the term “ THCV ” comprises any derivative and /or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of THCV and a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis OH tering purified THCV and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering THCV and a first purified HO psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri [0126 ] Within the context of this disclosure , the term fied THCV and a first purified psilocybin derivative . “ CBCA ” comprises any derivative and /or salt thereof. In US 2019 /0142851 A1 May 16 , 2019 one embodiment, the compositions and methods disclosed 0131 ] As used herein , the term “ CBD ” refers to a com herein comprise administering a formulation of CBCA and pound with the following structural formula : a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified CBCA and a first psilocybin derivative. In one embodiment, the compositions and methods disclosed herein comprise administering CBCA and a first purified psilocybin derivative . In one embodiment, the compositions H OH and methods disclosed herein comprise administering puri fied CBCA and a first purified psilocybin derivative . [0127 ] As used herein , the term “ CBCV ” refers to a compound with the following structural formula : HO

[0132 ] Within the context of this disclosure , the term “ CBD ” comprises any derivative and /or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBD and a first psilocybin derivative . In one embodiment, the compo sitions and methods disclosed herein comprise administer ing purified CBD and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering CBD and a first purified HO psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri fied CBD and a first purified psilocybin derivative . [0128 ] Within the context of this disclosure , the term 0133 ] As used herein , the term “ CBDA ” refers to a “ CBCV ” comprises any derivative and /or salt thereof. In compound with the following structural formula : one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBCV and a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified CBCV and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed H OH O herein comprise administering CBCV and a first purified psilocybin derivative. In one embodiment , the compositions and methods disclosed herein comprise administering puri ( ? fied CBCV and a first purified psilocybin derivative. [0129 ] As used herein , the term “ CBCVA ” refers to a HO compound with the following structural formula : 10134 ] Within the context of this disclosure , the term “ CBDA ” comprises any derivative and / or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBDA and a first psilocybin derivative. In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified CBDA and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering CBDA and a first purified OH psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri HO fied CBDA and a first purified psilocybin derivative . [0135 ] As used herein , the term “ CBDV ” refers to a compound with the following structural formula : [ 0130 ] Within the context of this disclosure , the term “ CBCVA ” comprises any derivative and / or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBCVA and a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified CBCVA and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering CBCVA and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri HO fied CBCVA and a first purified psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019

[0136 ] Within the context of this disclosure , the term [0141 ] As used herein , the term “ CBGA ” refers to a “ CBDV ” comprises any derivative and / or salt thereof. In compound with the following structural formula : one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBDV and a first psilocybin derivative. In one embodiment, the com OH O positions and methods disclosed herein comprise adminis tering purified CBDV and a first psilocybin derivative. In OH one embodiment, the compositions and methods disclosed herein comprise administering CBDV and a first purified HO psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering puri [ 0142 ] Within the context of this disclosure , the term fied CBDV and a first purified psilocybin derivative . “ CBGA ” comprises any derivative and / or salt thereof. In [0137 ] As used herein , the term “ CBDVA ” refers to a one embodiment, the compositions and methods disclosed compound with the following structural formula : herein comprise administering a formulation of CBGA and a first psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering purified CBGA and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering CBGA and a first purified OH O psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering puri OH fied CBGA and a first purified psilocybin derivative . [0143 ] As used herein , the term “ CBGV” refers to a ?? compound with the following structural formula :

[0138 ] Within the context of this disclosure , the term ?? “ CBDVA ” comprises any derivative and /or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBDVA and a first psilocybin derivative. In one embodiment, the com HO positions and methods disclosed herein comprise adminis tering purified CBDVA and a first psilocybin derivative . In [0144 ] Within the context of this disclosure , the term one embodiment, the compositions and methods disclosed “ CBGV ” comprises any derivative and / or salt thereof. In herein comprise administering CBDVA and a first purified one embodiment, the compositions and methods disclosed psilocybin derivative . In one embodiment, the compositions herein comprise administering a formulation of CBGV and and methods disclosed herein comprise administering puri a first psilocybin derivative . In one embodiment, the com fied CBDVA and a first purified psilocybin derivative . positions and methods disclosed herein comprise adminis tering purified CBGV and a first psilocybin derivative . In [ 0139 ] As used herein , the term “ CBG ” refers to a com one embodiment, the compositions and methods disclosed pound with the following structural formula : herein comprise administering CBGV and a first purified psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering puri OH fied CBGV and a first purified psilocybin derivative . [0145 ] As used herein , the term “ CBGVA ” refers to a compound with the following structural formula :

HO OH

[ 0140 ] Within the context of this disclosure , the term OH " CBG ” comprises any derivative and /or salt thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of CBG and a HO first psilocybin derivative. In one embodiment, the compo sitions and methods disclosed herein comprise administer [0146 ] Within the context of this disclosure , the term ing purified CBG and a first psilocybin derivative . In one “ CBGVA " comprises any derivative and /or salt thereof. In embodiment, the compositions and methods disclosed one embodiment, the compositions and methods disclosed herein comprise administering CBG and a first purified herein comprise administering a formulation of CBGVA and psilocybin derivative . In one embodiment, the compositions a first psilocybin derivative . In one embodiment, the com and methods disclosed herein comprise administering puri positions and methods disclosed herein comprise adminis fied CBG and a first purified psilocybin derivative. tering purified CBGVA and a first psilocybin derivative . In US 2019 /0142851 A1 May 16 , 2019 one embodiment, the compositions and methods disclosed between about 5 : 1 to about 1 : 5 of the first purified psilocybin herein comprise administering CBGVA and a first purified derivative and the sum of the first purified cannabinoid and psilocybin derivative . In one embodiment, the compositions the second purified cannabinoid . and methods disclosed herein comprise administering puri [0161 ] In one embodiment, the compositions and methods fied CBGVA and a first purified psilocybin derivative . disclosed herein comprise administering a first terpene . In [0147 ] In one embodiment, the compositions disclosed one embodiment, the first terpene is a first purified terpene . herein comprise a particular ratio ( e . g ., a molar ratio ) [0162 ] As used herein , the term “ terpene ” refers to a between about 100 : 1 to about 1 : 100 of the first purified compound belonging to a large class of compounds often psilocybin derivative and the first purified cannabinoid . biosynthesized from 5 - carbon isoprene units . In one [0148 ] In one embodiment, the compositions disclosed embodiment, a terpene is produced by a variety of plants , herein comprise a particular ratio ( e . g ., a molar ratio ) e . g . , conifers , cannabis , basil , etc . In one embodiment, a between about 75 : 1 to about 1: 75 of the first purified terpene is produced by an insect, e . g . , termites or swallow psilocybin derivative and the first purified cannabinoid . tail butterflies . In one embodiment, a terpene is a volatile [ 0149 ] In one embodiment, the compositions disclosed compound . In one embodiment , a terpene produces an odor. herein comprise a particular ratio ( e . g ., a molar ratio ) In one embodiment, a terpene is a major component of a between about 50 : 1 to about 1 : 50 of the first purified natural resin , e . g . , turpentine produced from resin . In one psilocybin derivative and the first purified cannabinoid . embodiment, a terpene is derived biosynthetically from units [0150 ] In one embodiment, the compositions disclosed of isoprene , which has the molecular formula C Hg. In one herein comprise a particular ratio ( e . g ., a molar ratio ) embodiment, the molecular formula of terpenes are mul between about 25 : 1 to about 1 : 25 of the first purified tiples of (C3H )n , where n is the number of linked isoprene psilocybin derivative and the first purified cannabinoid . units . [0151 ] In one embodiment, the compositions disclosed 10163 ]. Within the context of this disclosure when a ter herein comprise a particular ratio ( e . g . , a molar ratio ) pene is modified chemically , such as by oxidation or rear between about 10 : 1 to about 1 : 10 of the first purified rangement of the carbon skeleton , the resulting compound is psilocybin derivative and the first purified cannabinoid . referred to as a terpenoid . In the relevant arts , terpenoids are [0152 ] In one embodiment, the compositions disclosed sometimes referred to as isoprenoids . herein comprise a particular ratio ( e . g . , a molar ratio ) [0164 ] In one embodiment, a terpene is the primary con between about 5 : 1 to about 1 : 5 of the firstpurified psilocybin stituent or constituents of an essential oil from a plant and / or derivative and the first purified cannabinoid . flower . Essential oils are used widely as fragrances in 10153] In one embodiment, the compositions and methods perfumery, medicine, and alternative medicines , e . g ., aro disclosed herein comprise a first purified psilocybin deriva matherapy. tive , a first purified cannabinoid , and a second purified [0165 ] In one embodiment, a terpene is categorized cannabinoid . according to the number of isoprene (C3Hz ) units in the 10154 ] In one embodiment, the second purified cannabi compound , for example , a monoterpene (C10H16 ) , a sesqui noid is chosen from THC , THCA , THCV , THCVA , CBC , terpene (C15H24 ), a diterpene (C20H32 ) , a triterpene CBCA , CBCV , CBCVA , CBD , CBDA , CBDV, CBDVA , ( C30H48 ), or a tetraterpene ( C40H64 ). CBG , CBGA , CBGV, or CBGVA . [0166 ] In one embodiment , a first purified terpene is [0155 ] In one embodiment, the compositions disclosed chosen from acetanisole , acetyl cedrene , anethole , anisole , herein comprise a particular ratio ( e . g ., a molar ratio ) benzaldehyde , bornyl acetate , borneol, cadinene, cafestol, between about 100 : 1 to about 1 : 100 of the first purified caffeic acid , camphene, camphor , capsaicin , carene , caro psilocybin derivative and the sum of the first purified tene , carvacrol, carvone , alpha - caryophyllene , beta cannabinoid and the second purified cannabinoid . caryophyllene , caryophyllene oxide , cedrene, cedrene epox [0156 ] In one embodiment, the compositions disclosed ide , cecanal, cedrol, cembrene , cinnamaldehyde , cinnamic herein comprise a particular ratio ( e . g . , a molar ratio ) acid , citronellal , citronellol, cymene, eicosane, elemene, between about 75 : 1 to about 1 : 75 of the first purified estragole , ethyl acetate, ethyl cinnamate , ethyl maltol, euca psilocybin derivative and the sum of the first purified lyptol/ 1 , 8 - cineole, eudesmol, eugenol, euphol, farnesene , cannabinoid and the second purified cannabinoid . farnesol, fenchone , geraniol, geranyl acetate , guaia - 1 ( 10 ) , [ 0157 ] In one embodiment, the compositions disclosed 11 -diene , guaiacol, guaiol, guaiene, gurjunene , herniarin , herein comprise a particular ratio ( e . g ., a molar ratio ) hexanaldehyde , hexanoic acid , humulene , ionone, ipsdienol, between about 50 : 1 to about 1 : 50 of the first purified isoamyl acetate , isoamyl alcohol, isoamyl formate, isobor psilocybin derivative and the sum of the first purified neol, isomyrcenol, isoprene, isopulegol, isovaleric acid , cannabinoid and the second purified cannabinoid . lavandulol, limonene , gamma - linolenic acid , linalool, lon [0158 ] In one embodiment, the compositions disclosed gifolene , lycopene , menthol , methyl butyrate , 3 -mercapto herein comprise a particular ratio ( e . g ., a molar ratio ) 2 -methylpentanal , beta -mercaptoethanol , mercaptoacetic between about 25 : 1 to about 1 : 25 of the first purified acid , methyl salicylate , methylbutenol, methyl - 2 -methylva psilocybin derivative and the sum of the first purified lerate , methyl thiobutyrate , beta -myrcene , gamma cannabinoid and the second purified cannabinoid . muurolene , nepetalactone, nerol, nerolidol, neryl acetate , [0159 ] In one embodiment, the compositions disclosed nonanaldehyde , nonanoic acid , ocimene , octanal, octanoic herein comprise a particular ratio ( e . g ., a molar ratio ) acid , pentyl butyrate , phellandrene , phenylacetaldehyde, between about 10 : 1 to about 1 : 10 of the first purified phenylacetic acid , phenylethanethiol, phytol , pinene , propa psilocybin derivative and the sum of the first purified nethiol, pristimerin , pulegone , retinol, rutin , sabinene , cannabinoid and the second purified cannabinoid . squalene , taxadiene, terpineol, terpine - 4 - ol, terpinolene , thu 0160 ] In one embodiment, the compositions disclosed jone , thymol, umbelliferone , undecanal, verdoxan , or van herein comprise a particular ratio ( e . g . , a molar ratio ) illin . US 2019 /0142851 A1 May 16 , 2019

[0167 ] In one embodiment, a first purified terpene is [0172 ] As used herein , the term “ borneol” refers to a chosen from bornyl acetate , alpha -bisabolol , borneol, cam compound with the following structural formula : phene , camphor, carene , beta -caryophyllene , cedrene , cymene, elemene , eucalyptol, eudesmol, farnesene, fenchol, geraniol, guaiacol, humulene, isoborneol, limonene , lina lool, menthol, beta -myrcene , nerolidol, ocimene, phellan drene , phytol, pinene, pulegone, sabinene , terpineol, terpi nolene , or valencene . [0168 ] As used herein , the term “ bornyl acetate ” refers to a compound with the following structural formula : OH [0173 ] Within the context of this disclosure , the term “ borneol” comprises any derivative and / or salt thereof, including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of borneol and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering a formulation of purified borneol and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of borneol and a first [0169 ] Within the context of this disclosure, the term purified psilocybin derivative . In one embodiment, the com " bornyl acetate ” comprises any derivative and /or salt positions and methods disclosed herein comprise adminis thereof, including any isomeric , structural and / or enantio tering a formulation of purified borneol and a first purified meric , variations thereof. In one embodiment, the compo psilocybin derivative . sitions and methods disclosed herein comprise administer 10174 ]. As used herein , the term " camphene ” refers to a ing a formulation of bornyl acetate and a first psilocybin compound with the following structural formula : derivative. In one embodiment, the compositions and meth ods disclosed herein comprise administering a formulation of purified bornyl acetate and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of bornyl acetate and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified bornyl acetate and a first purified psilocybin derivative . 10175 ]. Within the context of this disclosure , the term [0170 ] As used herein , the term “ alpha - bisabolol ” refers to " camphene” comprises any derivative and /or salt thereof, a compound with the following structural formula : including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of camphene and a first psilocybin derivative . In one HO embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified camphene and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of camphene and a first purified psilocybin derivative. In one embodiment, the com positions and methods disclosed herein comprise adminis [0171 ] Within the context of this disclosure , the term tering a formulation of purified camphene and a first purified “ alpha -bisabolol ” comprises any derivative and /or salt psilocybin derivative . thereof, including any isomeric , structural and / or enantio [0176 ] As used herein , the term " camphor ” refers to a meric , variations thereof. In one embodiment, the compo compound with either of the following structural formulas : sitions and methods disclosed herein comprise administer ing a formulation of alpha -bisabolol and a first psilocybin derivative. In one embodiment, the compositions and meth ods disclosed herein comprise administering a formulation of purified alpha - bisabolol and a first psilocybin derivative . In one embodiment, the compositions and methods dis closed herein comprise administering a formulation of alpha - bisabolol and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified alpha -bisabolol and a first purified psilocybin derivative. US 2019 /0142851 A1 May 16 , 2019 13

[0177 ] Within the context of this disclosure , the term o ds disclosed herein comprise administering a formulation " camphor” comprises any derivative and / or salt thereof, of purified beta - caryophyllene and a first purified psilocybin including any isomeric , structural and / or enantiomeric , derivative . variations thereof. In one embodiment, the compositions and 10182 ]. As used herein , the term “ cedrene ” refers to a methods disclosed herein comprise administering a formu lation of camphor and a first psilocybin derivative . In one compound with either of the following structural formulas: embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified camphor and a first psilocybin derivative . In one embodi ment , the compositions and methods disclosed herein com prise administering a formulation of camphor and a first purified psilocybin derivative . In one embodiment, the com CH3 ch ; l CH3 CH3 CH3 LH CHz. positions and methods disclosed herein comprise adminis tering a formulation of purified camphor and a first purified CH3 psilocybin derivative . VuiCH? L | . [0178 ] As used herein , the term " carene” refers to a CH3 compound with the following structural formula : [0183 ] Within the context of this disclosure , the term " cedrene” comprises any derivative and / or salt thereof, including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of cedrene and a first psilocybin derivative . In one [0179 ] Within the context of this disclosure , the term embodiment , the compositions and methods disclosed “ carene ” comprises any derivative and / or salt thereof, herein comprise administering a formulation of purified including any isomeric , structural, and / or enantiomeric , cedrene and a first psilocybin derivative . In one embodi variations thereof. In one embodiment , the compositions and ment, the compositions and methods disclosed herein com methods disclosed herein comprise administering a formu prise administering a formulation of cedrene and a first lation of carene and a first psilocybin derivative . In one purified psilocybin derivative . In one embodiment, the com embodiment, the compositions and methods disclosed positions and methods disclosed herein comprise adminis herein comprise administering a formulation of purified tering a formulation of purified cedrene and a first purified carene and a first psilocybin derivative. In one embodiment, psilocybin derivative . the compositions and methods disclosed herein comprise [0184 ] As used herein , the term " cymene ” refers to a administering a formulation of carene and a first purified compound with the following structural formula : psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified carene and a first purified psilocybin derivative . [0180 ] As used herein , the term “ beta - caryophyllene” H3CCH3. refers to a compound with the following structural formula :

CH3 [0185 ] Within the context of this disclosure , the term " cymene” comprises any derivative and / or salt to thereof, 10181 ] Within the context of this disclosure, the term including any isomeric , structural and/ or enantiomeric , “ beta - caryophyllene” comprises any derivative and / or salt variations thereof. In one embodiment, the compositions and thereof, including any isomeric , structural and / or enantio methods disclosed herein comprise administering a formu meric , variations thereof . In one embodiment, the compo lation of cymene and a first psilocybin derivative . In one sitions and methods disclosed herein comprise administer embodiment, the compositions and methods disclosed ing a formulation of beta - caryophyllene and a first herein comprise administering a formulation of purified psilocybin derivative . In one embodiment, the compositions cymene and a first psilocybin derivative . In one embodi and methods disclosed herein comprise administering a ment, the compositions and methods disclosed herein com formulation of purified beta - caryophyllene and a first psilo prise administering a formulation of cymene and a first cybin derivative . In one embodiment, the compositions and purified psilocybin derivative . In one embodiment, the com methods disclosed herein comprise administering a formu positions and methods disclosed herein comprise adminis lation of beta - caryophyllene and a first purified psilocybin tering a formulation of purified cymene and a first purified derivative . In one embodiment, the compositions and meth - psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019 14

[0186 ] As used herein , the term “ elemene” refers to a [0190 ] As used herein , the term “ eudesmol” refers to a compound with the following structural formula : compound with either of the following structural formulas :

H O HO

[0191 ] Within the context of this disclosure , the term “ eudesmol” comprises any derivative and / or salt thereof, including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of eudesmol and a first psilocybin derivative. In one [0187 ] Within the context of this disclosure , the term embodiment, the compositions and methods disclosed " elemene” comprises any derivative and /or salt thereof, herein comprise administering a formulation of purified including any isomeric , structural, and / or enantiomeric , eudesmol and a first psilocybin derivative . In one embodi variations thereof. In one embodiment, the compositions and ment, the compositions and methods disclosed herein com methods disclosed herein comprise administering a formu prise administering a formulation of eudesmol and a first lation of elemene and a first psilocybin derivative . In one purified psilocybin derivative . In one embodiment, the com embodiment, the compositions and methods disclosed positions and methods disclosed herein comprise adminis herein comprise administering a formulation of purified tering a formulation of purified eudesmol and a first purified elemene and a first psilocybin derivative . In one embodi psilocybin derivative . ment, the compositions and methods disclosed herein com [0192 ] As used herein , the term " farnesene ” refers to a prise administering a formulation of elemene and a first compound with the following structural formula : purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified elemene and a first purified psilocybin derivative . [0188 ] As used herein , the term “ eucalyptol” refers to a compound with the following structural formula : [0193 ] Within the context of this disclosure , the term “ farnesene” comprises any derivative and /or salt thereof, including any isomeric , structural , and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of farnesene and a first psilocybin derivative. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified farnesene and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of farnesene and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified farnesene and a first purified [0189 ] Within the context of this disclosure , the term psilocybin derivative . “ eucalyptol” comprises any derivative and / or salt thereof, [0194 ] As used herein , the term " fenchol” refers to a including any isomeric , structural and / or enantiomeric , compound with the following structural formula : variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of eucalyptol and a first psilocybin derivative . In one CH3 embodiment, the compositions and methods disclosed A CH3. herein comprise administering a formulation of purified eucalyptol and a first psilocybin derivative . In one embodi VOH ment, the compositions and methods disclosed herein com CH3 prise administering a formulation of eucalyptol and a first purified psilocybin derivative. In one embodiment, the com [0195 ] Within the context of this disclosure , the term positions and methods disclosed herein comprise adminis “ fenchol” comprises any derivative and / or salt thereof , tering a formulation of purified eucalyptol and a first purified including any isomeric , structural, and / or enantiomeric , psilocybin derivative . variations thereof. In one embodiment, the compositions and US 2019 /0142851 A1 May 16 , 2019 15 methods disclosed herein comprise administering a formu [0200 ] As used herein , the term “ humulene ” refers to a lation of fenchol and a first psilocybin derivative . In one compound with the following structural formula : embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified fenchol and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of fenchol and a first purified psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified fenchol and a first purified psilocybin derivative . [0196 ] As used herein , the term " geraniol” refers to a 10201 ] Within the context of this disclosure , the term compound with the following structural formula : " humulene” comprises any derivative and / or salt thereof, including any isomeric , structural, and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of humulene and a first psilocybin derivative . In one ?? . embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified humulene and a first psilocybin derivative . In one embodi [0197 ] Within the context of this disclosure , the term ment, the compositions and methods disclosed herein com “ geraniol” comprises any derivative and /or salt thereof, prise administering a formulation of humulene and a first including any isomeric , structural and /or enantiomeric , purified psilocybin derivative. In one embodiment, the com variations thereof. In one embodiment , the compositions and positions and methods disclosed herein comprise adminis methods disclosed herein comprise administering a formu tering a formulation ofpurified humulene and a first purified lation of geraniol and a first psilocybin derivative . In one psilocybin derivative. embodiment, the compositions and methods disclosed [0202 ] As used herein , the term “ isoborneol” refers to a herein comprise administering a formulation of purified compound with the following structural formula : geraniol and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of geraniol and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified geraniol and a first purified psilocybin derivative. OH . [0198 ] As used herein , the term “ guaiacol” refers to a compound with the following structural formula : [0203 ]. Within the context of this disclosure , the term " isoborneol” comprises any derivative and /or salt thereof, including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu CH3 lation of isoborneol and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified OH . isoborneol and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of isoborneol and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis [019 ] Within the context of this disclosure , the term tering a formulation of purified isoborneol and a first puri " guaiacol” comprises any derivative and/ or salt thereof, fied psilocybin derivative . including any isomeric , structural, and /or enantiomeric , [0204 ] As used herein , the term “ limonene ” refers to a variations thereof. In one embodiment, the compositions and compound with the following structural formula : methods disclosed herein comprise administering a formu lation of guaiacol and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified guaiacol and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of guaiacol and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified guaiacol and a first purified psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019 16

[0205 ] Within the context of this disclosure , the term [0210 ] As used herein , the term “ beta - myrcene” refers to " limonene ” comprises any derivative and /or salt thereof, a compound with the following structural formula : including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of limonene and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified limonene and a first psilocybin derivative . In one embodi [0211 ] Within the context of this disclosure , the term ment, the compositions and methods disclosed herein com “ beta -myrcene ” comprises any derivative and / or salt prise administering a formulation of limonene and a first thereof, including any isomeric , structural and / or enantio purified psilocybin derivative . In one embodiment, the com meric , variations thereof. In one embodiment, the compo positions and methods disclosed herein comprise adminis sitions and methods disclosed herein comprise administer tering a formulation of purified limonene and a first purified ing a formulation of beta -myrcene and a first psilocybin psilocybin derivative . derivative . In one embodiment, the compositions and meth [ 0206 ] As used herein , the term “ linalool” refers to a ods disclosed herein comprise administering a formulation compound with the following structural formula : of purified beta -myrcene and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of beta HO myrcene and a first purified psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering a formulation of purified beta -myrcene and a first purified psilocybin derivative . [0207 ] Within the context of this disclosure , the term [0212 ] As used herein , the term “ nerolidol” refers to a “ linalool” comprises any derivative and /or salt thereof, compound with the following structural formula : including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu HO lation of linalool and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified linalool and a first psilocybin derivative. In one embodi [0213 ] Within the context of this disclosure , the term ment, the compositions and methods disclosed herein com " nerolidol” comprises any derivative and / or salt thereof, prise administering a formulation of linalool and a first including any isomeric , structural, and / or enantiomeric , purified psilocybin derivative . In one embodiment, the com variations thereof. In one embodiment, the compositions and positions and methods disclosed herein comprise adminis methods disclosed herein comprise administering a formu tering a formulation of purified linalool and a first purified lation of nerolidol and a first psilocybin derivative . In one psilocybin derivative . embodiment, the compositions and methods disclosed [0208 ] As used herein , the term “ menthol” refers to a herein comprise administering a formulation of purified compound with the following structural formula : nerolidol and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of nerolidol and a first CH3. purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis CH3 tering a formulation of purified nerolidol and a first purified psilocybin derivative . [0214 ] As used herein , the term " ocimene ” refers to a CH ? OH compound with the following structural formula : [ 0209] Within the context of this disclosure , the term " menthol” comprises any derivative and / or salt thereof, including any isomeric , structural and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of menthol and a first psilocybin derivative . In one [0215 ] Within the context of this disclosure , the term embodiment, the compositions and methods disclosed “ ocimene ” comprises any derivative and / or salt thereof, herein comprise administering a formulation of purified including any isomeric , structural, and / or enantiomeric , menthol and a first psilocybin derivative . In one embodi variations thereof. In one embodiment, the compositions and ment, the compositions and methods disclosed herein com methods disclosed herein comprise administering a formu prise administering a formulation of menthol and a first lation of ocimene and a first psilocybin derivative . In one purified psilocybin derivative . In one embodiment, the com embodiment, the compositions and methods disclosed positions and methods disclosed herein comprise adminis herein comprise administering a formulation of purified tering a formulation of purified menthol and a first purified ocimene and a first psilocybin derivative . In one embodi psilocybin derivative . ment, the compositions and methods disclosed herein com US 2019 /0142851 A1 May 16 , 2019 prise administering a formulation of ocimene and a first [0220 ] As used herein , the term “ pinene ” refers to a purified psilocybin derivative . In one embodiment, the com compound with the following structural formula : positions and methods disclosed herein comprise adminis tering a formulation of purified ocimene and a first purified psilocybin derivative. [0216 ] As used herein , the term “ phellandrene ” refers to a compound with the following structural formula :

[0221 ] Within the context of this disclosure , the term " pinene ” comprises any derivative and /or salt thereof, including any isomeric , structural, and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of pinene and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise administering a formulation of purified pinene and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of pinene and a first purified [ 0217] Within the context of this disclosure , the term psilocybin derivative . In one embodiment , the compositions " phellandrene” comprises any derivative and /or salt thereof, and methods disclosed herein comprise administering a including any isomeric , structural, and / or enantiomeric , formulation of purified pinene and a first purified psilocybin variations thereof. In one embodiment, the compositions and derivative . methods disclosed herein comprise administering a formu [0222 ] As used herein , the term “ pulegone” refers to a lation of phellandrene and a first psilocybin derivative . In compound with the following structural formula : one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified phellandrene and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed CH3. herein comprise administering a formulation of phellan drene and a first purified psilocybin derivative . In one CH3 embodiment, the compositions and methods disclosed CH , herein comprise administering a formulation of purified phellandrene and a first purified psilocybin derivative . [0223 ]. Within the context of this disclosure , the term [0218 ] As used herein , the term “ phytol” refers to a “ pulegone” comprises any derivative and /or salt thereof, compound with the following structural formula : including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of pulegone and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified pulegone and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com whhh ?? . prise administering a formulation of pulegone and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified pulegone and a first purified psilocybin derivative . [ 0219] Within the context of this disclosure , the term [0224 ] As used herein , the term " sabinene ” refers to a " phytol ” comprises any derivative and / or salt thereof, compound with the following structural formula : including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu CH , lation of phytol and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified phytol and a first psilocybin derivative . In one embodiment , the compositions and methods disclosed herein comprise CH3 administering a formulation of phytol and a first purified psilocybin derivative . In one embodiment, the compositions [0225 ] Within the context of this disclosure , the term and methods disclosed herein comprise administering a “ sabinene” comprises any derivative and/ or salt thereof, formulation of purified phytol and a first purified psilocybin including any isomeric , structural, and /or enantiomeric , derivative . variations thereof. In one embodiment, the compositions and US 2019 /0142851 A1 May 16 , 2019 methods disclosed herein comprise administering a formu - positions and methods disclosed herein comprise adminis lation of sabinene and a first psilocybin derivative . In one tering a formulation of purified terpinolene and a first embodiment, the compositions and methods disclosed purified psilocybin derivative. herein comprise administering a formulation of purified [0230 ] As used herein , the term “ valencene” refers to a sabinene and a first psilocybin derivative . In one embodi compound with the following structural formula : ment, the compositions and methods disclosed herein com prise administering a formulation of sabinene and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis tering a formulation of purified sabinene and a first purified psilocybin derivative . [ 0226 ] As used herein , the term “ terpineol” refers to a compound with the following structural formula : [0231 ] Within the context of this disclosure, the term “ valencene” comprises any derivative and /or salt thereof, including any isomeric , structural, and / or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of valencene and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed LOH . herein comprise administering a formulation of purified valencene and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of valencene and a first [0227 ] Within the context of this disclosure , the term purified psilocybin derivative . In one embodiment , the com “ terpineol” comprises any derivative and / or salt thereof, positions and methods disclosed herein comprise adminis including any isomeric , structural, and / or enantiomeric , tering a formulation of purified valencene and a first purified variations thereof. In one embodiment, the compositions and psilocybin derivative . methods disclosed herein comprise administering a formu [0232 ] In one embodiment, the compositions and methods lation of terpineol and a first psilocybin derivative . In one disclosed herein include one or more purified erinacine embodiment, the compositions and methods disclosed molecules. In one embodiment, the compositions and meth herein comprise administering a formulation of purified ods disclosed herein comprise purified erinacine A . In one terpineol and a first psilocybin derivative . In one embodi embodiment, the compositions and methods disclosed ment, the compositions and methods disclosed herein com herein comprise erinacine B . In one embodiment, the com prise administering a formulation of terpineol and a first positions and methods disclosed herein comprise erinacine purified psilocybin derivative. In one embodiment, the com C . In one embodiment, the compositions and methods positions and methods disclosed herein comprise adminis disclosed herein comprise erinacine D . In one embodiment , tering a formulation of purified terpineol and a first purified the compositions and methods disclosed herein comprise psilocybin derivative . erinacine E . In one embodiment, the compositions and (0228 ] As used herein , the term “ terpinolene ” refers to a methods disclosed herein comprise erinacine F . In one compound with the following structural formula : embodiment, the compositions and methods disclosed herein comprise erinacine G . In one embodiment , the com positions and methods disclosed herein comprise erinacine H . In one embodiment, the compositions and methods disclosed herein comprise erinacine I . In one embodiment, the compositions and methods disclosed herein comprise erinacine J . In one embodiment, the compositions and methods disclosed herein comprise erinacine K . In one embodiment, the compositions and methods disclosed herein comprise erinacine P . In one embodiment, the com positions and methods disclosed herein comprise erinacine Q . In one embodiment, the compositions and methods [ 0229 ] Within the context of this disclosure , the term disclosed herein comprise erinacine R . In one embodiment, “ terpinolene " comprises any derivative and /or salt thereof, the compositions and methods disclosed herein comprise including any isomeric , structural, and / or enantiomeric , erinacine S . In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise one or more purified methods disclosed herein comprise administering a formu erinacinemolecules and purified pyridine -3 - carboxylic acid . lation of terpinolene and a first psilocybin derivative . In one In one embodiment, the compositions and methods dis embodiment, the compositions and methods disclosed closed herein comprise one or more purified erinacine herein comprise administering a formulation of purified molecules and a purified cannabinoid , such as CBD . terpinolene and a first psilocybin derivative . In one embodi 0233 ] As used herein , the term " erinacine A ” refers to a ment, the compositions and methods disclosed herein com molecule with the following structural formula : prise administering a formulation of terpinolene and a first [0234 ] Within the context of this disclosure , the term purified psilocybin derivative . In one embodiment, the com " erinacine A ” comprises any derivative and /or salt thereof, US 2019 /0142851 A1 May 16 , 2019 19

including any isomeric , structural and / or enantiomeric , [0237 ] As used herein , the term “ erinacine C ” refers to a variations thereof. In one embodiment, the compositions and compound with the following structural formula : methods disclosed herein comprise administering a formu lation of erinacine A and a first psilocybin derivative. In one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified erinacine A and a first psilocybin

OH til

OH

OH 0238 ] Within the context of this disclosure , the term HOY " erinacine C ” comprises any derivative and /or salt thereof, including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu lation of erinacine C and a first psilocybin derivative . In one derivative . In one embodiment, the compositions and meth embodiment, the compositions and methods disclosed ods disclosed herein comprise administering a formulation herein comprise administering a formulation of purified of erinacine A and a first purified psilocybin derivative . In erinacine C and a first psilocybin derivative . In one embodi one embodiment, the compositions and methods disclosed ment, the compositions and methods disclosed herein com herein comprise administering a formulation of purified prise administering a formulation of erinacine C and a first erinacine A and a first purified psilocybin derivative . purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis [ 0235 ] As used herein , the term “ erinacine B ” refers to a tering a formulation of purified erinacine C and a first compound with the following structural formula : purified psilocybin derivative . [ 0239 ] As used herein , the term “ erinacine D ” refers to a compound with the following structural formula :

??

OH HO ÕH

[ 0236 ] Within the context of this disclosure , the term [ 0240 ] Within the context of this disclosure , the term " erinacine B ” comprises any derivative and / or salt thereof, “ erinacine D ” comprises any derivative and /or salt thereof, including any isomeric , structural and / or enantiomeric , including any isomeric , structural and / or enantiomeric , variations thereof. In one embodiment , the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of erinacine B and a first psilocybin derivative . In one lation of erinacine D and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified herein comprise administering a formulation of purified erinacine B and a first psilocybin derivative . In one embodi erinacine D and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine B and a first prise administering a formulation of erinacine D and a first purified psilocybin derivative . In one embodiment, the com purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis positions and methods disclosed herein comprise adminis tering a formulation of purified erinacine B and a first tering a formulation of purified erinacine D and a first purified psilocybin derivative. purified psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019 20

[0241 ] As used herein , the term " erinacine E ” refers to a [0245 ] As used herein , the term “ erinacine G ” refers to a compound with the following structural formula : compound with the following structural formula :

11111111

HP - - OH H - ) OH OH - OH

HO ?? HO OH

[ 0242 ] Within the context of this disclosure , the term [0246 ] Within the context of this disclosure , the term " erinacine E ” comprises any derivative and /or salt thereof, “ erinacine G ” comprises any derivative and /or salt thereof, including any isomeric , structural and / or enantiomeric , including any isomeric , structural and / or enantiomeric , variations thereof. In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of erinacine E and a first psilocybin derivative. In one lation of erinacine G and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified herein comprise administering a formulation of purified erinacine E and a first psilocybin derivative. In one embodi erinacine G and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine E and a first prise administering a formulation of erinacine G and a first purified psilocybin derivative. In one embodiment, the com purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis positions and methods disclosed herein comprise adminis tering a formulation of purified erinacine E and a first tering a formulation of purified erinacine G and a first purified psilocybin derivative . purified psilocybin derivative . [0243 ] As used herein , the term “ erinacine F ” refers to a [0247 ] As used herein , the term " erinacine H ” refers to a compound with the following structural formula : compound with the following structural formula :

OH H — ?? O OH OH - OHOH HO OH

[0244 ] Within the context of this disclosure , the term [0248 ] Within the context of this disclosure , the term " erinacine F ” comprises any derivative and /or salt thereof, " erinacine H ” comprises any derivative and /or salt thereof, including any isomeric , structural and / or enantiomeric , including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of erinacine F and a first psilocybin derivative . In one lation of erinacine H and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified herein comprise administering a formulation of purified erinacine F and a first psilocybin derivative . In one embodi erinacine H and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine F and a first prise administering a formulation of erinacine H and a first purified psilocybin derivative. In one embodiment, the com purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis positions and methods disclosed herein comprise adminis tering a formulation of purified erinacine F and a first tering a formulation of purified erinacine H and a first purified psilocybin derivative . purified psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019 21

[0249 ] As used herein , the term “ erinacine I” refers to a [0253 ] As used herein , the term “ erinacine K ” refers to a compound with the following structural formula : compound with the following structural formula :

OH OH H ORI ??

[0250 ] Within the context of this disclosure , the term [0254 ] Within the context of this disclosure , the term “ erinacine I” comprises any derivative and /or salt thereof, “ erinacine K ” comprises any derivative and /or salt thereof, including any isomeric , structural and /or enantiomeric , including any isomeric , structural and / or enantiomeric , variations thereof. In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of erinacine I and a first psilocybin derivative . In one lation of erinacine K and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified herein comprise administering a formulation of purified erinacine I and a first psilocybin derivative . In one embodi erinacine K and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine I and a first prise administering a formulation of erinacine K and a first purified psilocybin derivative . In one embodiment , the com purified psilocybin derivative. In one embodiment, the com positions and methods disclosed herein comprise adminis positions and methods disclosed herein comprise adminis tering a formulation of purified erinacine I and a first purified tering a formulation of purified erinacine K and a first psilocybin derivative . purified psilocybin derivative . [0251 ] As used herein , the term “ erinacine J” refers to a [0255 ] As used herein , the term " erinacine P ” refers to a compound with the following structural formula : compound with the following structural formula :

OH - 0 H i - .. ???? HOBI

mo H OH

[ 0252] Within the context of this disclosure , the term [ 0256 ] Within the context of this disclosure , the term " erinacine J ” comprises any derivative and / or salt thereof, " erinacine P ” comprises any derivative and /or salt thereof , including any isomeric , structural and / or enantiomeric , including any isomeric , structural and/ or enantiomeric , variations thereof. In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of erinacine J and a first psilocybin derivative . In one lation of erinacine P and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified herein comprise administering a formulation of purified erinacine J and a first psilocybin derivative . In one embodi erinacine P and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine J and a first prise administering a formulation of erinacine P and a first purified psilocybin derivative . In one embodiment, the com purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis positions and methods disclosed herein comprise adminis tering a formulation of purified erinacine J and a first tering a formulation of purified erinacine P and a first purified psilocybin derivative . purified psilocybin derivative . US 2019 /0142851 A1 May 16 , 2019

[0257 ] As used herein , the term “ erinacine Q ” refers to a [0261 ] As used herein , the term “ erinacine S ” refers to a compound with the following structural formula : compound with the following structural formula :

OH H 1111

OH OH

[ 0262 ] Within the context of this disclosure , the term " erinacine S ” comprises any derivative and /or salt thereof, [0258 ] Within the context of this disclosure , the term including any isomeric , structural and / or enantiomeric , " erinacine Q ” comprises any derivative and / or salt thereof, variations thereof. In one embodiment, the compositions and including any isomeric , structural and/ or enantiomeric , methods disclosed herein comprise administering a formu variations thereof. In one embodiment , the compositions and lation of erinacine S and a first psilocybin derivative . In one methods disclosed herein comprise administering a formu embodiment, the compositions and methods disclosed lation of erinacine Q and a first psilocybin derivative. In one herein comprise administering a formulation of purified embodiment, the compositions and methods disclosed erinacine S and a first psilocybin derivative . In one embodi herein comprise administering a formulation of purified ment , the compositions and methods disclosed herein com erinacine Q and a first psilocybin derivative . In one embodi prise administering a formulation of erinacine S and a first ment, the compositions and methods disclosed herein com purified psilocybin derivative . In one embodiment, the com prise administering a formulation of erinacine Q and a first positions and methods disclosed herein comprise adminis purified psilocybin derivative . In one embodiment, the com tering a formulation of purified erinacine S and a first positions and methods disclosed herein comprise adminis purified psilocybin derivative. tering a formulation of purified erinacine Q and a first [0263 ] The erinacine chemical structures are taken from Li purified psilocybin derivative . 1 - C , Lee L - Y , Tzeng T W , et al. Neurohealth properties of [0259 ] As used herein , the term " erinacine R ” refers to a Hericium erinaceus mycelia enriched with erinacines . In : compound with the following structural formula : Behavioural Neurology . 2018 . doi: 10 .1155 / 2018 / 5802634 [ 0264 ] In one embodiment , the compositions and methods disclosed herein include one or more purified hericenone molecules . In one embodiment, the compositions and meth ods disclosed herein comprise purified hericenone A . In one embodiment, the compositions and methods disclosed herein comprise purified hericenone B . In one embodiment , OH the compositions and methods disclosed herein comprise purified hericenone C . In one embodiment, the compositions » Ho and methods disclosed herein comprise purified hericenone En D . In one embodiment , the compositions and methods disclosed herein comprise purified hericenone E . In one embodiment, the compositions and methods disclosed herein comprise purified hericenone F . In one embodiment, the compositions and methods disclosed herein comprise purified hericenone G . In one embodiment, the compositions [ 0260 ] Within the context of this disclosure , the term and methods disclosed herein comprise purified hericenone " erinacine R ” comprises any derivative and/ or salt thereof, H . including any isomeric , structural and / or enantiomeric , variations thereof. In one embodiment, the compositions and [0265 ] As used herein , the term “ hericenone A ” refers to methods disclosed herein comprise administering a formu a molecule with the following structural formula : lation of erinacine R and a first psilocybin derivative . In one embodiment, the compositions and methods disclosed OH herein comprise administering a formulation of purified erinacine R and a first psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of erinacine R and a first purified psilocybin derivative . In one embodiment, the com positions and methods disclosed herein comprise adminis www tering a formulation of purified erinacine R and a first purified psilocybin derivative. US 2019 /0142851 A1 May 16 , 2019

[0266 ] Within the context of this disclosure , the term lation of hericenone C and a first psilocybin derivative. In " hericenone A ” comprises any derivative and /or salt thereof, one embodiment, the compositions and methods disclosed including any isomeric , structural and / or enantiomeric , herein comprise administering a formulation of purified variations thereof. In one embodiment, the compositions and hericenone C and a first psilocybin derivative . In one methods disclosed herein comprise administering a formu embodiment , the compositions and methods disclosed lation of hericenone A and a first psilocybin derivative . In herein comprise administering a formulation of hericenone one embodiment , the compositions and methods disclosed C and a first purified psilocybin derivative. In one embodi herein comprise administering a formulation of purified ment , the compositions and methods disclosed herein com hericenone A and a first psilocybin derivative. In one prise administering a formulation of purified hericenone C embodiment, the compositions and methods disclosed and a first purified psilocybin derivative . herein comprise administering a formulation of hericenone (0274 ] Within the context of this disclosure , the term A and a first purified psilocybin derivative . In one embodi “ hericenone D ” comprises any derivative and / or salt thereof, ment, the compositions and methods disclosed herein com including any isomeric, structural and / or enantiomeric , prise administering a formulation of purified hericenone A variations thereof. In one embodiment, the compositions and and a first purified psilocybin derivative. methods disclosed herein comprise administering a formu [ 0267 ] As used herein , the term “ hericenone B ” refers to lation of hericenone D and a first psilocybin derivative . In a compound with the following structural formula : one embodiment, the compositions and methods disclosed herein comprise administering a formulation of purified hericenone D and a first psilocybin derivative . In one OH embodiment, the compositions and methods disclosed herein comprise administering a formulation of hericenone D and a first purified psilocybin derivative . In one embodi ment, the compositions and methods disclosed herein com prise administering a formulation of purified hericenone D PH , and a first purified psilocybin derivative . [0275 ] Within the context of this disclosure , the term " hericenone E ” comprises any derivative and /or salt thereof, [0268 ] Within the context of this disclosure , the term including any isomeric , structural and /or enantiomeric , " hericenone B ” comprises any derivative and /or salt thereof, variations thereof. In one embodiment, the compositions and including any isomeric , structural and / or enantiomeric , methods disclosed herein comprise administering a formu variations thereof. In one embodiment, the compositions and lation of hericenone E and a first psilocybin derivative. In methods disclosed herein comprise administering a formu one embodiment, the compositions and methods disclosed lation of hericenone B and a first psilocybin derivative . In herein comprise administering a formulation of purified one embodiment, the compositions and methods disclosed hericenone E and a first psilocybin derivative . In one herein comprise administering a formulation of purified embodiment, the compositions and methods disclosed hericenone B and a first psilocybin derivative . In one herein comprise administering a formulation of hericenone embodiment, the compositions and methods disclosed E and a first purified psilocybin derivative . In one embodi herein comprise administering a formulation of hericenone ment, the compositions and methods disclosed herein com B and a first purified psilocybin derivative . In one embodi prise administering a formulation of purified hericenone E ment, the compositions and methods disclosed herein com and a first purified psilocybin derivative . prise administering a formulation of purified hericenone B [0276 ] As used herein , the terms “ hericenone F, ” “ heri and a first purified psilocybin derivative. cenone G , ” and “ hericenone H ” refer to compounds with the [0269 ] As used herein , the terms “ hericenone C ," " heri following structural formula a with substituents as indicated : cenone D , ” and “ hericenone E ” refer to compounds with the following structural formula with substituents as indicated :

OH OH OH OR tie OR

[0277 ] Hericenone F : R = palmitoyl [0270 ] Hericenone C : R = palmitoyl [0278 ] Hericenone G : R = stearoyl [0271 ] Hericenone D : R = stearoyl [ 0279 ] Hericenone H : R = linoleoyl [0272 ] Hericenone E : R = linoleoyl 102801 Within the context of this disclosure , the term [ 0273 ] Within the context of this disclosure , the term “ hericenone F ” comprises any derivative and / or salt thereof , “ hericenone C ” comprises any derivative and / or salt thereof, including any isomeric, structural and / or enantiomeric , including any isomeric , structural and /or enantiomeric , variations thereof. In one embodiment, the compositions and variations thereof. In one embodiment, the compositions and methods disclosed herein comprise administering a formu methods disclosed herein comprise administering a formu lation of hericenone F and a first psilocybin derivative. In US 2019 /0142851 A1 May 16 , 2019 24 one embodiment, the compositions and methods disclosed compositions and methods disclosed herein comprise herein comprise administering a formulation of purified administering a formulation of purified pyridine - 3 - carbox hericenone F and a first psilocybin derivative . In one ylic acid and a first psilocybin derivative . In one embodi embodiment, the compositions and methods disclosed ment, the compositions and methods disclosed herein com herein comprise administering a formulation of hericenone prise administering a formulation of pyridine - 3 - carboxylic F and a first purified psilocybin derivative . In one embodi acid and a first purified psilocybin derivative . In one ment, the compositions and methods disclosed herein com embodiment, the compositions and methods disclosed prise administering a formulation of purified hericenone F herein comprise administering a formulation of purified and a first purified psilocybin derivative . pyridine -3 -carboxylic acid and a first purified psilocybin [0281 ] Within the context of this disclosure , the term derivative . “ hericenone G ” comprises any derivative and / or salt thereof, [0286 ] In one embodiment, the compositions and methods including any isomeric , structural and /or enantiomeric , disclosed herein include one or more purified hericenone variations thereof. In one embodiment , the compositions and molecules and one or more purified erinacine molecules . methods disclosed herein comprise administering a formu [0287 ] In one embodiment, the compositions and methods lation of hericenone G and a first psilocybin derivative . In disclosed herein include one or more purified psilocybin one embodiment, the compositions and methods disclosed derivatives , one or more purified hericenone molecules and herein comprise administering a formulation of purified one or more purified erinacine molecules . hericenone G and a first psilocybin derivative . In one [0288 ] In one embodiment, the compositions and methods embodiment, the compositions and methods disclosed disclosed herein include one or more purified psilocybin herein comprise administering a formulation of hericenone derivatives , one or more purified hericenone molecules , one G and a first purified psilocybin derivative . In one embodi or more purified erinacine molecules and one or more ment, the compositions and methods disclosed herein com purified cannabinoids. prise administering a formulation of purified hericenone G 02891. In one embodiment, the compositions and methods and a first purified psilocybin derivative . disclosed herein include one or more purified psilocybin [ 0282] Within the context of this disclosure , the term derivatives , one or more purified hericenone molecules , one “ hericenone H ” comprises any derivative and /or salt thereof, or more purified erinacine molecules and purified pyridine including any isomeric , structural and / or enantiomeric , 3 -carboxylic acid . variations thereof. In one embodiment, the compositions and 0290 ] In one embodiment, the compositions and methods methods disclosed herein comprise administering a formu disclosed herein include one or more purified psilocybin lation of hericenone H and a first psilocybin derivative . In derivatives and one or more purified molecules attained by one embodiment , the compositions and methods disclosed extracting and subsequently purifying one or more com herein comprise administering a formulation of purified pounds from an organism chosen from Bacopa monnieri ( for hericenone H and a first psilocybin derivative . In one example, the purified molecule bacoside A3 ) , Centella asi embodiment, the compositions and methods disclosed atica ( for example , the purified molecule asiaticoside ) , herein comprise administering a formulation of hericenone Gingko biloba ( for example , the purified molecule myrice H and a first purified psilocybin derivative. In one embodi tin ) , Zingiber officinale ( for example , the purified molecule ment, the compositions and methods disclosed herein com zingerone) , Ocimum sanctum ( for example , the purified prise administering a formulation of purified hericenone H molecule linalool) , Polygonum cuspidatum ( for example , and a first purified psilocybin derivative . the purified molecule resveratrol) , Origanum vulgare ( for [ 0283] In one embodiment, the compositions and methods example , the purified molecule carvacrol) , Origanum onites disclosed herein comprise one or more purified hericenone ( for example , the purified molecule thymol) , Rosmarinus molecules and purified pyridine - 3 - carboxylic acid . In one officinalis ( for example , the purified molecule rosmarinic embodiment, the compositions and methods disclosed acid ) , Rosmarinus eriocalyx ( for example , the purified mol herein comprise one or more purified hericenone molecules ecule camphor ), Curcuma longa ( for example , the purified and a purified cannabinoid , such as CBD . molecule curcumin ), Camellia sinensis ( for example , the [ 0284 ] As used herein , the term " pyridine - 3 - carboxylic purified molecule theobromine ) , Lavandula spica (for acid ” refers to a molecule with the following structural example , the purified molecule caryophyllene) , Scutellaria formula : lateriflora ( for example , the purified molecule baicalin ) , Avena sativa ( for example , the purified molecule avenalin ) , Avena byzantina ( for example , the purified molecule beta glucan ) , Salvia divinorum ( for example, the purified mol ecule salvinorin A ), Banisteriopsis caapi ( for example , the OH purified molecule harmine ), Psychotria species ( for example, the purified molecule dimethyltryptamine ), Taber nanthe iboga ( for example , the purified molecule ibogaine ), Voacanga africana ( for example , the purified molecule voacangine ), Tabernaemontana undulata (for example , the [ 0285 ] Within the context of this disclosure , the term purified molecule ibogamine ) , Lophophora williamsii ( for " pyridine - 3 - carboxylic acid ” comprises any derivative and / example , the purified moleculemescaline ), Ipomoea tricolor or salt thereof, including any isomeric , structural and /or ( for example , the purified molecule ergonovine ) , and /or enantiomeric , variations thereof. In one embodiment, the Argyreia nervosa ( for example , the purified molecule compositions and methods disclosed herein comprise ergine ) . administering a formulation of pyridine - 3 - carboxylic acid [0291 ] In one embodiment, the compositions disclosed and a first psilocybin derivative . In one embodiment, the herein comprise a particular ratio ( e . g ., a molar ratio ) US 2019 /0142851 A1 May 16 , 2019 25 between about 100 :1 to about 1 : 100 of the first purified ratio (e .g ., a molar ratio ) between about 5 : 1 to about 1: 5 of psilocybin derivative and the first purified terpene . the first purified psilocybin derivative and the first purified [ 0292] In one embodiment, the compositions disclosed terpene . herein comprise a particular ratio ( e . g . , a molar ratio ) [0304 ] In one embodiment, a first purified terpene modu between about 75 : 1 to about 1 : 75 of the first purified lates the activity of a neurotransmitter activity modulator, psilocybin derivative and the first purified terpene . e . g ., a serotonergic drug , an adrenergic drug , a dopaminergic [0293 ] In one embodiment, the compositions disclosed drug , a psilocybin derivative, etc . herein comprise a particular ratio ( e . g ., a molar ratio ) [0305 ] As used herein , the term “ serotonergic drug ” refers between about 50 : 1 to about 1 :50 of the first purified to a compound that binds to , blocks , or otherwise influences psilocybin derivative and the first purified terpene . ( e . g . , via an allosteric reaction ) activity at a serotonin [0294 ] In one embodiment, the compositions disclosed receptor. In one embodiment, a serotonergic drug binds to a herein comprise a particular ratio ( e . g ., a molar ratio ) serotonin receptor. In one embodiment, a serotonergic drug between about 25 : 1 to about 1 : 25 of the first purified indirectly affects a serotonin receptor, e. g . , via interactions psilocybin derivative and the first purified terpene . affecting the reactivity of other molecules at the serotonin [ 0295 ] In one embodiment, the compositions disclosed receptor. In one embodiment, a serotonergic drug is an herein comprise a particular ratio ( e . g . , a molar ratio ) agonist , e. g ., a compound activating a serotonin receptor . In between about 10 : 1 to about 1 : 10 of the first purified one embodiment, a serotonergic drug is an antagonist, e . g . , psilocybin derivative and the first purified terpene . a compound binding but not activating a serotonin receptor, [0296 ] In one embodiment, the compositions disclosed e . g ., blocking a receptor. In one embodiment, a serotonergic herein comprise a particular ratio ( e . g . , a molar ratio ) drug is an effector molecule , e . g . , a compound binding to an between about 5 : 1 to about 1 : 5 of the first purified psilocybin enzyme for allosteric regulation . In one embodiment, a derivative and the first purified terpene . serotonergic drug acts ( either directly or indirectly ) at more [ 0297 ] In one embodiment, the compositions and methods than one type of receptor ( e . g . , SHT, dopamine , adrenergic , disclosed herein comprise a first purified psilocybin deriva acetylcholine , etc . ) . tive, a first purified cannabinoid , and a first purified terpene . [ 0306 ] In one embodiment, a serotonergic drug is an [ 0298 ] In one embodiment, the compositions disclosed antidepressant. herein comprise a particular ratio ( e . g ., a molar ratio ) [0307 ] In one embodiment, a serotonergic drug is an between about 100 : 1 to about 1 : 100 of the first purified anxiolytic . psilocybin derivative and the first purified cannabinoid and [0308 ] In one embodiment , a serotonergic drug is a selec a particular ratio ( e. g ., a molar ratio ) between about 100 :1 to tive serotonin reuptake inhibitor. about 1 : 100 of the first purified psilocybin derivative and the [0309 ] In one embodiment, a serotonergic drug is a selec first purified terpene . tive serotonin norepinephrine reuptake inhibitor. [0299 ] In one embodiment, the compositions disclosed [ 0310 ] Some exemplary serotonergic drugs include the herein comprise a particular ratio ( e . g . , a molar ratio ) following molecules : 4 -hydroxy - N -methyltryptamine ( aka between about 75 : 1 to about 1 : 75 of the first purified 3 [ 2 - (methylamino ) ethyl) - 1H - indol- 4 - ol) , aeruginascin (aka psilocybin derivative and the first purified cannabinoid and [ 3 - [ 2 - ( trimethylazaniumyl) ethyl] - 1H - indol- 4 - yl] hydrogen a particular ratio (e . g. , a molar ratio ) between about 75 : 1 to phosphate ) , baeocystin ( aka [ 3 - [ 2 - (methylamino ) ethyl] - 1H about 1 : 75 of the first purified psilocybin derivative and the indol - 4 - yl] dihydrogen phosphate ) , bufotenidine ( aka 3 - [ 2 first purified terpene. (trimethylazaniumypethyl ] - 1H - indol- 5 -olate ), bufotenin [0300 ] In one embodiment, the compositions disclosed (aka 3 -[ 2 -( dimethylamino )ethyl ] -1H - indol -5 -ol ) , ethocybin herein comprise a particular ratio ( e . g . , a molar ratio ) (aka [ 3 - [ 2 - (diethylamino ) ethyl ] - 1H - indol- 4 - yl] dihydrogen between about 50 : 1 to about 1 :50 of the first purified phosphate ) , norbaeocystin (aka [ 3 - ( 2 - aminoethyl) - 1H - in psilocybin derivative and the first purified cannabinoid and dol - 4 - yl] dihydrogen phosphate ) , norpsilocin , psilocin ( aka a particular ratio ( e . g ., a molar ratio ) between about 50 : 1 to 3 - 52 - ( dimethylamino ) ethyl) - 1H - indol- 4 -ol ) , psilocybin (aka about 1 :50 of the first purified psilocybin derivative and the [ 3 - [ 2 - ( dimethylamino ) ethyl] - 1H - indol- 4 -yl ] dihydrogen first purified terpene . phosphate ) , serotonin (aka 3 - ( 2 -aminoethyl ) - 1H - indol- 5 -ol ) , [0301 ] In one embodiment, the compositions disclosed 1P -LSD ( aka ( 6aR , 9R ) - N , N - diethyl- 7 -methyl - 4 - propanoyl herein comprise a particular ratio ( e . g ., a molar ratio ) 6 , 6a, 8 , 9 - tetrahydroindolo [ 4 , 3 - fg ] quinoline - 9 - carboxam between about 25 : 1 to about 1 : 25 of the first purified ide ), ALD - 52 (aka (6aR , 9R ) - 4 - acetyl- N , N - diethyl- 7 psilocybin derivative and the first purified cannabinoid and methyl- 6 ,6a , 8 , 9 - tetrahydroindolo [ 4 , 3 - fglquinoline - 9 a particular ratio ( e . g ., a molar ratio ) between about 25 : 1 to carboxamide ), AL -LAD ( aka (6aR ,9R ) - N , N -diethyl - 7 -prop about 1 : 25 of the first purified psilocybin derivative and the 2 -enyl - 6 ,6a , 8 , 9 -tetrahydro - 4H - indolo?4 , 3 - fg ]quinoline - 9 first purified terpene . carboxamide ) , BU -LAD ( aka (6R ,9R ) - 7 -butyl - N , N [ 0302 ] In one embodiment, the compositions disclosed diethyl- 6 ,6a ,8 ,9 - tetrahydro -4H - indolo [ 4, 3 - fg ] quinoline - 9 herein comprise a particular ratio ( e . g ., a molar ratio ) carboxamide) , DAL (aka (6aR , 9R ) - 7 -methyl - N , N -bis (prop between about 10 : 1 to about 1 : 10 of the first purified 2 -enyl ) - 6 , 6a ,8 , 9 -tetrahydro - 4H - indolo [ 4 , 3 - fg ] quinoline - 9 psilocybin derivative and the first purified cannabinoid and carboxamide ) , DAM -57 ( aka (6aR , 9R ) - N , N , 7 - trimethyl -6 , a particular ratio ( e . g . , a molar ratio ) between about 10 : 1 to 6a, 8 , 9 - tetrahydro -4H - indolo [ 4 , 3 - fglquinoline - 9 about 1 : 10 of the first purified psilocybin derivative and the carboxamide ) , EIPLA ( aka (6aR , 9R ) - N - ethyl- 7 -methyl - N first purified terpene . propan - 2 - yl- 6 ,6a , 8 , 9 - tetrahydro -4H - indolo [ 4 , 3 - fg ] [0303 ] In one embodiment, the compositions disclosed quinoline - 9 -carboxamide ), ETH -LAD ( aka 6R( , 9R ) - N , N , herein comprise a particular ratio ( e . g . , a molar ratio ) 7 - triethyl - 6 ,6a , 8 , 9 - tetrahydro - 4H - indolo [ 4 , 3 - fg ]quinoline between about 5 : 1 to about 1 : 5 of the first purified psilocybin 9 -carboxamide ) , LAE - 32 ( aka (6aR , 9R ) - N - ethyl- 7 -methyl derivative and the first purified cannabinoid and a particular 6 , 6 , 8 , 9 - tetrahydro -4H - indolo [ 4 , 3 - fglquinoline - 9 US 2019 /0142851 A1 May 16 , 2019 26 carboxamide ), LPD -824 (aka [ (6aR , 9R )- 7 -methyl - 6 ,6a ,8 , 9 N - dimethylethanamine ), 5 -MeO - DPT ( aka N - [ 2 - ( 5 tetrahydro -4H - indolo [4 ,3 - fg ]quinoline -9 -yl ] - pyrrolidin -1 methoxy - 1H - indol- 3 - yl) ethyl] - N - propylpropan - 1 - amine ) , ylmethanone ) , LSB (aka (6aR , 9R ) - N -butan - 2 -yl - 7 -methyl 5 -MeO - EiPT (aka N - ethyl- N -[ 2 - (5 -methoxy - 1H -indol - 3 -yl ) 6 ,6 , 8 , 9 - tetrahydro -4H - indolo [ 4 , 3 - fg ]quinoline - 9 ethyl ]propan - 2 - amine ) , 5 -MeO -MALT (aka N - [ 2 - ( 5 carboxamide ), LSA ( aka 6R( , 9R ) - 7 -methyl - 6 ,6 , 8 , 9 Methoxy - 1H - indol- 3 -yl ) ethyl] -N -methylprop - 2 -en -1 tetrahydro -4H - indolo [ 4 , 3 - fg ] quinoline - 9 - carboxamide ) , amine ) , 5 -MeO -MiPT ( aka N - [ 2 - ( 5 -methoxy - 1H - indol LSD -25 ( aka 6R( ,9R ) - N , N - diethyl- 7 -methyl - 6 ,6a ,8 , 9 - tet - 3 - yl ) ethyl] - N - methylpropan - 2 -amine ) , 5 -MeO -NMT ( aka rahydro - 4H - indolo [ 4 , 3 - fglquinoline - 9 - carboxamide ) , LSD 2 - ( 5 -methoxy - 1H - indol- 3 - yl) - N -methylethanamine ;hydro PiP (aka (7 -methyl - 6 ,6a , 8 , 9 -tetrahydro -4H - indolo [4 , 3 - fg ] chloride ), 5 -MeO -pyr - T (aka 4 - fluoro - 5 -methoxy - 3 -( 2 -pyr quinoline - 9 -yl ) - piperidin - 1 -ylmethanone ) , LSM -775 (aka rolidin - 1 - ylethyl) - 1H - indole ), 5 -MeO - TMT ( aka 2 - ( 5 [ 6R( , 9R )- 7 -methyl -6 , 6 , 8 ,9 - tetrahydro -4H - indolo [4 ,3 - fg ] methoxy - 2 -methyl - 1H - indol - 3 - yl )- N , N quinoline - 9 - yl] -morpholin - 4 -ylmethanone ), LSP ( aka (6R , dimethylethanamine ), 5 -MeS - DMT (aka N ,N -dimethyl - 2 9R ) - 7 -methyl - N - pentan - 3 -yl - 6 ,6a , 8 , 9 - tetrahydro - 4H - indolo ( 5 -methylsulfanyl - 1H - indol - 3 - yl) ethanamine ) , 5 ,6 -MDO 54 , 3 - fg ] quinoline - 9 -carboxamide ), LSZ ( aka [ (6aR , 9R ) - 7 DIPT (aka N - [ 2 - (5H - [ 1 , 3 ]dioxolo [ 4 , 5 - f ]indol - 7 - yl) ethyl] methyl- 6 , 6 , 8 , 9 - tetrahydro -4H - indolo [ 4 , 3 - fglquinoline- 9 N -propan -2 - ylpropan - 2 - amine ), 5, 6 -MDO -DMT (aka yl] - [ (2S ,4S ) - 2 , 4 - dimethylazetidin - 1 - yl) methanone ) , 2 -( 5H - [ 1, 3 ] dioxolo [ 4 , 5 - f ]indol - 7 - yl) - N , N - dimethylethan methergine (aka (6R , 9R ) -N -( 1 -hydroxybutan -2 -yl ) - 7 amine ), 5 ,6 -MDO -MIPT (aka N - [ 2 - (5H - [ 1 , 3 ] dioxolo [ 4 , 5 - f ] methyl- 6 ,6a , 8 , 9 - tetrahydro - 4H - indolo [ 4 , 3 - fg ] quinoline - 9 indol- 7 - yl) ethyl] - N -ethylpropan - 2 - amine) , 5 ,6 -MeO -MIPT carboxamide ) , MiPLA ( aka (6aR , 9R ) - N , 7 - dimethyl- N -pro ( aka N - 2 - ( 5 , 6 - dimethoxy - 1H - indol - 3 - yl) ethyl ] - N -methyl pan - 2 -yl - 6 , 6 , 8 , 9 - tetrahydro -4H - indolo [ 4 ,3 -fg ]quinoline - 9 propan - 2 - amine ) , 5 , N , N - TMT ( aka N , N - dimethyl- 2 - (5 carboxamide ), NDTDI, PARGY- LAD , PRO -LAD (aka methyl- 1H - indol- 3 - ethanamine ), 6 - MeO - THH ( aka (6aR ,9R ) - N ,N -diethyl - 7 -propyl - 6 ,6a , 8 , 9 - tetrahydro - 4H - in 6 -methoxy - 1 -methyl - 2 ,3 , 4 , 9 -tetrahydro - 1H -pyrido [ 3 , 4 -b ] dolo [ 4 , 3 - fg ] quinoline - 9 - carboxamide ), 2 -Me - DET ( aka indole ) , alpha -ET (aka 1 - 1H - indol- 3 - yl) butan - 2 -amine ) , N , N - diethyl - 2 - ( 2 -methyl - 1H - indol- 3 - yl) ethanamine ) , alpha -MT ( aka 1 - 1H - indol- 3 - yl) propan - 2 -amine ) , alpha 2 -Me - DMT ( aka N , N - dimethyl - 2 - ( 2 -methyl - 1H - indol- 3 - yl) TMT (aka 1 - ( 1H -indol - 3 - yl) - N , N -dimethylpropan - 2 ethanamine ) , 2 ,alpha -DMT ( aka 1 - ( 2 -methyl - 1H - indol- 3 - yl) amine ), alpha , N -DMT (aka 2 - ( 1H - indol- 3 -yl ) - N , N -dim propan - 2 - amine ) , 4 - AcO - DALT ( aka [ 3 - [ 2 - [bis (prop - 2 ethylethanamine ) , alpha, N , O - TMS (aka 1 -( 5 -methoxy -1H enyl ) amino ) ethyl) - 1H - indol- 4 - yl] acetate ), 4 - AcO -DET indol- 3 - yl) - N -methylpropan - 2 - amine ) , alpha , O - DMS ( aka ( aka [ 3 - [ 2 - ( diethylamino )ethyl ) - 1H - indol- 4 - yl] acetate ) , 1 - ( 5 -methoxy - 1H - indol- 3 -yl ) propan - 2 - amine ) , DALT ( aka 4 -AcO -DIPT (aka 3 -[ 2 -( Diisopropylamino )ethyl ) - 1H - indol N - [ 2 - ( 1H - indol- 3 -ypethyl ] - N - prop - 2 - enylprop - 2 - en - 1 4 - yl acetate ) , 4 - AcO - DMT (aka [ 3 - [ 2 - ( dimethylamino ) amine ) , DBT ( aka N - butyl- N - [ 2 - ( 1H - indol- 3 - yl) ethyl] bu ethyl ] -1H - indol- 4 - yl] acetate ), 4 - AcO - DPT ( aka [ 3 - [ 2 tan - 1 - amine ), DET (aka N , N - diethyl- 2 -( 1H - indol- 3 - yl) ( dipropylamino ) ethyl] - 1H -indol - 4 - yl] acetate ), 4 - AcO - EPT ethanamine ), DiPT ( aka N - [ 2 - ( 5 -methoxy - 1H - indol- 3 - yl) ( aka 3 - { 2 - [ Ethyl ( propyl ) amino ) ethyl} - 1H - indol - 4 - yl ethyl] - N - propan - 2 - ylpropan - 2 - amine ), DMT ( aka 2 - ( 1H acetate ) , 4 - AcO -MET (aka [ 3 - [ 2 - [ ethyl( methyl ) amino ] indol- 3 - yl) - N , N - dimethylethanamine ) , DPT ( aka N - [ 2 - 1H ethyl] - 1H - indol- 4 - yl] acetate ) , 4 - AcO -MIPT ( aka [ 3 - [ 2 indol- 3 -yl ) ethyl] -N -propylpropan -1 - amine ), EiPT ( aka [methyl ( propan - 2 -yl ) aminoJethyl ] - 1H - indol- 4 -yl ] acetate ), N - ethyl - N - [ 2 - ( 1H - indol- 3 - yl) ethyl] propan - 2 - amine ), Har 4 -AcO -MPT , 4 - HO - DBT ( aka 3 -[ 2 - ( dibutylamino ) ethyl] maline (aka 7 -methoxy - 1 -methyl - 3 , 4 -dihydro -2H -pyrido 1H - indol - 4 - ol) , 4 -HO -DET (aka 3 - [ 2 - ( diethylamino )ethyl ) [ 3 , 4 - b ] indole ) , Harmine (aka 7 -methoxy - 1 -methyl - 9H 1H - indol - 4 -ol ) , 4 -HO - DIPT (aka 3 - [ 2 - [ di( propan - 2 - yl) pyrido [ 3 ,4 - b ] indole) , MALT , MBT ( aka 3H - 1 ,3 -benzothiaz amino ) ethyl ] - 1H - indol - 4 - ol) , 4 -HO -DPT ( aka 3 - [ 2 ole - 2 - thione ), Melatonin (aka N - [ 2 - ( 5 -methoxy - 1H - indol- 3 ( dipropylamino )ethyl ) - 1H - indol- 4 - ol) , 4 - HO -EPT , 4 -HO yl) ethyllacetamide ) , MET ( aka N -ethyl - 2 - ( 1H - indol- 3 -yl ) MCPT, 4 - HO -MET ( aka 3 - [ 2 - [ ethyl( methyl ) amino ) ethyl] N -methylethanamine ) , MiPT ( aka N - [ 2 - ( 1H - indol- 3 -yl ) 1H - indol - 4 -01 ) , 4 -HO -MIPT (aka 3 - [ 2 - [methyl (propan - 2 - yl) ethyl) - N -methylpropan - 2 - amine ) , MPT (aka 3 - [ 2 - [methyl amino ) ethyl] - 1H - indol- 4 - ol) , 4 - HO -MPMI ( aka 3 - [ ( 1 (propyl ) amino ) ethyl] - 1H - indol- 4 -ol ) , NET (aka N - ethyl- 2 methylpyrrolidin - 2 - yl )methyl )- 1H - indol -4 - ol) , 4 -HO -MPT ( 1H - indol- 3 -yl ) ethanamine ) , NMT (aka 2 - ( 1H - indol- 3 - yl) ( aka 3 - [ 2 - [methyl ( propyl ) amino ) ethyl] - 1H - indol- 4 - ol) , N -methylethanamine ), PiPT ( aka N - [ 2 - ( 1H - indol- 3 -yl ) 4 - HO -pyr - T (aka 3 - ( 2 -pyrrolidin - 1 -ylethyl ) - 1H - indol - 4 - ol) , ethyl ] - N - propan - 2 - ylpropan - 1 - amine ) , pyr- T ( aka 3 - ( 2 4 -MeO -MIPT ( aka N - [ 2 - ( 4 -methoxy - 1H - indol- 3 - yl) ethyl] pyrrolidin - 1 -ylethyl ) - 1H - indole ) , T (aka 2 -( 1H - indol- 3 - yl) N -methylpropan - 2 -amine ) , 4 ,5 -MDO -DIPT (aka N -[ 2 - C6H ethanamine ), Tetrahydroharmine (aka 7 -methoxy - 1- methyl [ 1 , 3 ] dioxolo [ 4 , 5 - e ] indol- 8 - yl) ethyl] - N -propan - 2 -ylpropan 2 ,3 , 4 , 9 -tetrahydro - 1H - pyrido [ 3 , 4 - b ]indole ) , 2 - Br- 4 , 5 -MDA 2 - amine ), 4 ,5 -MDO -DMT (aka 2 - (6H -[ 1, 3 ]dioxolo [4 ,5 - e ] (aka 1 -( 6 - bromo- 1 , 3 -benzodioxol - 5 - yl) propan - 2 - amine ), indol- 8 - yl) - N , N - dimethylethanamine ) , 5 -BROMO - DMT 2 - TIM ( aka 2 - ( 3 ,4 - dimethoxy - 2 -methylsulfanylphenyl ) (aka 2 -( 5 -bromo - 1H - indol- 3 -yl ) - N ,N -dimethylethanamine ), ethanamine) , 2 - TOET ( aka 1 - ( 4 - ethyl - 5 -methoxy - 2 -methyl 5 - chloro -alpha -MT (aka 1 -( 5 - chloro - 1H - indol- 3 -yl ) propan sulfanylphenyl) propan -2 -amine ), 2 - TOM (aka 1 -( 5 2 - amine ), 5 - fluoro - AMT ( aka 1 - ( 5 - fluoro - 1H - indol- 3 - yl) methoxy -4 -methyl - 2 -methylsulfanylphenyl ) propan - 2 propan - 2 -amine ) , 5 -MeO -AET ( aka 1 -( 5 -methoxy - 1H - in amine ), 2 ,4 -DMA (aka 1- ( 2 ,4 -dimethoxyphenyl ) propan - 2 dol- 3 - yl) butan - 2 - amine ) , 5 -MEO - AMT ( aka 1 - ( 5 -methoxy amine ), 2 , 5 -DMA (aka 1 - ( 2 , 5 -dimethoxyphenyl ) propan - 2 1H - indol- 3 - yl) propan - 2 -amine ), 5 -MeO - DALT (aka N - [ 2 amine ) , 2C - B (aka 2 - ( 4 -bromo - 2 , 5 - dimethoxyphenyl) ( 5 -methoxy - 1H -indol - 3 - yl) ethyl ] - N -prop - 2 -enylprop -2 -en ethanamine) , 2C -C ( aka 2 -( 4 -chloro - 2 ,5 - dimethoxyphenyl) 1 - amine) , 5 -MeO -DET ( aka N , N - diethyl - 2 - ( 5 -methoxy - 1H ethanamine ), 2C - D ( aka 2 - ( 2 ,5 - dimethoxy - 4 -methylphenyl ) indol - 3 - yl) ethanamine) , 5 -MeO - DIPT ( aka N - [ 2 - ( 5 ethanamine ), 2C - E ( aka 2 - ( 4 - ethyl- 2 , 5 - dimethoxyphenyl) methoxy - 1H - indol- 3 - yl) ethyl ] - N - propan - 2 - ylpropan - 2 ethanamine ) , 2C - F ( aka 2 - ( 4 - fluoro - 2 , 5 - dimethoxyphenyl) amine ), 5 -MeO -DMT (aka 2 - (5 -methoxy -1H - indol- 3 -yl ) - N , ethanamine) , 2C - 6 ( aka 2 - ( 2 , 5 - dimethoxy - 3 , 4 US 2019 /0142851 A1 May 16 , 2019 27

dimethylphenylethanamine ), 2C - G -3 (aka 2 -( 4 ,7 dimethoxyphenyl) - N - [ (4 -methoxyphenyl ) methyl ] dimethoxy - 2 , 3 - dihydro - 1H - inden - 5 - yl) ethanamine ), ethanamine ), 25C -NBF (aka 2 -( 4 -chloro - 2 , 5 2C - G - 4 (aka 2 - (1 , 4 - dimethoxy -5 ,6 ,7 , 8 -tetrahydronaphtha dimethoxyphenyl ) - N - [ ( 2 - fluorophenyl) methyl ] ethanamine ), len - 2 -yl ) ethanamine ), 2C -G - 5 (aka CAS 207740 - 20 - 3 ), 25C -NBOH (aka 2 -( 4 -chloro - 2 ,5 -dimethoxyphenyl ) ethyl 2C - G - N ( aka 2 - ( 1 , 4 - dimethoxynaphthalen - 2 - yl) ethan aminolmethyl ] phenol) , 25C - NBOMe ( aka 2 -( 4 - chloro - 2 , 5 amine ) , 2C - H (aka 2 - ( 2 , 5 - dimethoxyphenyl) ethanamine ), dimethoxyphenyl) -N [ ( 2 -methoxyphenyl ) methyl ] ethan 2C - I ( aka 2 - ( 4 - iodo - 2 , 5 - dimethoxyphenyl) ethanamine ) , amine ), 25CN -NBOH ( aka 4 -[ 2 -[ (2 -hydroxyphenyl ) 2C - N (aka 2 - (2 ,5 -dimethoxy - 4 -nitrophenyl ) ethanamine) , methylaminolethyl) -2 , 5 -dimethoxybenzonitrile ), 25CN 2C -0 - 4 ( aka 2 -( 2 ,5 - dimethoxy - 4 -propan -2 - yloxyphenyl ) NBOMe ( aka CAS 1354632 - 16 - 8 ), 25D -NBOMe ( aka 2 - ( 2 , ethanamine ), 2C -P ( aka 2- ( 2 ,5 -dimethoxy -4 -propylphenyl ) 5 - dimethoxy - 4 -methylphenyl ) - N - [( 2 -methoxyphenyl ) ethanamine ), 2C -SE ( aka 2 - ( 2 , 5 - dimethoxy - 4 -methylsela methyl ] ethanamine ), 25E - NBOMe ( aka 2 - ( 4 - ethyl- 2 , 5 nylphenyl ) ethanamine ) , 2C - T ( aka 2 - ( 2 , 5 - dimethoxy - 4 dimethoxyphenyl ) -N4 ( 2 -methoxyphenyl )methyl ] methylsulfanylphenyl) ethanamine) , 2C - T - 13 (aka 2 -[ 2 ,5 ethanamine) , 25G -NBOMe (aka 2 -( 2 ,5 -dimethoxy -3 , 4 dimethoxy - 4 - ( 2 -methoxyethylsulfanyl )phenyl ] ethanamine ) , dimethylphenyl) - N - [ ( 2 -methoxyphenyl ) methyl ] 2C - T- 15 (aka 2 - (4 - cyclopropylsulfanyl- 2 , 5 -dimethoxyphe ethanamine ) , 25H -NBOMe (aka 2 - ( 2 , 5 - dimethoxyphenyl) nyl) ethanamine ), 2C - T - 17 ( aka 2 - ( 4 - butan - 2 - ylsulfanyl- 2 , 5 N - [ ( 2 -methoxyphenyl ) methyl ] ethanamine ) , 25H -NB34MD dimethoxyphenyl) ethanamine ) , 2C - T - 2 ( aka 2 - ( 4 - ethylsulfa ( aka N - ( 1 , 3 -benzodioxol - 5 - ylmethyl) - 2 -( 4 - iodo - 2 , 5 - dime nyl- 2 , 5 -dimethoxypheny ) ethanamine ) , 2C - T - 2 (aka 2 - [ 4 - ( 2 thoxyphenyl) ethanamine ), 251- NB30Me (aka 2 - (4 - iodo - 2, fluoroethylsulfanyl) - 2 , 5 -dimethoxyphenyl ] ethanamine ), 5 -dimethoxyphenyl ) - N -[ (3 -methoxyphenyl ) methyl ] ethan 2C - T - 4 (aka 2 - (2 ,5 -dimethoxy - 4 -propan - 2 -ylsulfanylpheny ) amine ) , 251- NB40Me ( aka 2 - ( 4 - iodo - 2 , 5 ethanamine ), 2C - T - 7 (aka 2 - ( 2 , 5 - dimethoxy - 4 - propylsulfa dimethoxyphenyl) - N -[ (4 -methoxyphenyl ) methyl ] nylphenyl) ethanamine ), 2C - T - 8 ( aka 2 - [4 - (cyclopropylm ethanamine ), 251- NBF ( aka N -[ (2 - fluorophenyl) methyl ] - 2 ethylsulfanyl) - 2 , 5 - dimethoxyphenyl] ethanamine ) , 2C - T - 9 ( 4 - iodo - 2 , 5 - dimethoxyphenyl) ethanamine ) , 251- NBMD ( aka 2 -( 4 -butylsulfanyl - 2 , 5 - dimethoxyphenylethanamine ), (aka N - (1 , 3 -benzodioxol - 4 -ylmethyl ) - 2 -( 4 - iodo -2 , 5 -dime 2C - TFM ( aka 2 - [ 2 , 5 - dimethoxy - 4 - ( trifluoromethyl) phenyl] thoxyphenyl) ethanamine ) , 251- NBOH (aka 2 - [ [ 2 - ( 4 - iodo - 2 , ethanamine ), 2T- MMDA - 3a ( aka 1 - ( 4 -methylsulfanyl - 1 , 3 5 -dimethoxyphenylethylamino ]methyl ]phenol ) , 251 benzodioxol- 5 - yl ) propan - 2 - amine ), 3 - T - TRIS (aka 2 - ( 3 , 4 NBOMe (aka 2 - (4 - iodo - 2, 5 - dimethoxyphenyl) - N -[ ( 2 diethoxy - 5 - ethylsulfanylphenyl) ethanamine ), 3 - TASB ( aka methoxyphenyl) methyl ] ethanamine) , 251P -NBOMe (aka 2 -( 3 - ethoxy -4 -ethylsulfanyl -5 -methoxyphenyl ) ethan 2 - ( 2 , 5 - dimethoxy - 4 - propan - 2 - ylphenyl) - N - [ ( 2 -methoxy amine ) , 3 - TE ( aka 2 - ( 4 - ethoxy - 3 -methoxy - 5 -methylsulfa pheny )methyl ] ethanamine ), 25N - NBOMe ( aka 2 - ( 2 , 5 - dime nylphenyl) ethanamine ), 3 - TFM (aka 2 - ( 2 , 4 -dimethoxy - 3 thoxy - 4 - nitrophenyl) - N - [ ( 2 -methoxypheny )methyl ] ethan methylsulfanylphenyl) ethanamine ), 3 - TM (aka 2 - (3 , 4 amine) , 25P -NBOMe ( aka 2 - ( 2 , 5 - dimethoxy - 4 dimethoxy - 5 -methylsulfanylphenylethanamine ), 3 - TME propylphenyl) - N - [ ( 2 -methoxyphenyl ) methyl ] ethanamine ) , ( aka 2 - ( 3 - ethylsulfanyl- 4 , 5 - dimethoxyphenyl) ethanamine ) , 25TFM - NBOMe (aka 2 - [ 2 , 5 -dimethoxy - 4 - ( trifluoromethyl) 3 - TSB ( aka 2 - ( 3 - ethoxy - 5 - ethylsulfanyl- 4 -methoxyphenyl ) phenyl ] - N - [ ( 2 -methoxyphenyl )methyl ] ethanamine ) , ethanamine ), 3 , 4 - DMA ( aka 1 - ( 3 , 4 - dimethoxyphenyl) pro 2CBCB - NBOMe ( aka 1 - [ (7R ) - 3 -bromo - 2 , 5 -dimethoxy - 7 pan - 2 - amine) , 3C - BZ ( aka 1 - ( 3 , 5 - dimethoxy - 4 - phenyl bicyclo [ 4 . 2 . 0 ] octa - 1 ( 6 ), 2 , 4 - trienyl] - N - [ ( 2 -methoxypheny ) methoxyphenyl) propan - 2 - amine ), 3C - E (aka 1 - ( 4 - ethoxy - 3 , methyl] methanamine ) , 2CBFly - NBOMe ( aka 2 - ( 4 -bromo 5 -dimethoxyphenyl ) propan - 2 - amine ) , 4 - Br - 3 , 5 -DMA ( aka 2 ,3 , 6 ,7 - tetrahydrofuro [ 2 ,3 - f ][ 1 ]benzofuran - 8 - yl) - N - [ ( 2 1 -( 4 -bromo -3 , 5 -dimethoxyphenyl ) propan -2 -amine ), 4 - D methoxyphenyl) methyl ] thanamine ), AEM (aka 1- (3 ,4 ,5 ( aka CAS 1020518 -87 - 9 ), 4 -MA (aka 1 -( 4 -methoxyphenyl ) trimethoxyphenyl) butan - 2 -amine ), AL (aka 2 - ( 3 , 5 propan - 2 - amine ) , 4 - T - TRIS ( aka 2 - ( 3 , 5 -diethoxy - 4 - ethyl dimethoxy - 4 - prop - 2 - enoxyphenyl) ethanamine ), ALEPH sulfanylphenyl ) ethanamine ), 4 - TASB ( aka 2 - ( 3 - ethoxy -4 (aka 1 - ( 2 , 5 - dimethoxy - 4 -methylsulfanylphenyl ) propan - 2 ethylsulfanyl- 5 -methoxyphenylethanamine ), 4 - TE ( aka amine ; hydrochloride ), ALEPH - 2 (aka 1 - ( 4 - ethylsulfanyl- 2 , 2 -( 4 -ethylsulfanyl - 3 ,5 -dimethoxyphenyl ) ethanamine ), 5 - dimethoxyphenyl) propan - 2 - amine ), ALEPH - 4 ( aka 1 - ( 2 , 4 - TIM ( aka 2 - ( 2 , 3 - dimethoxy - 4 -methylsulfanylphenyl ) 5 -dimethoxy -4 -propan - 2 -ylsulfanylphenyl ) propan - 2 ethanamine ), 4 - TM ( aka 2 - ( 3 , 5 -dimethoxy - 4 -methylsulfa amine) , ALEPH -6 ( aka 1 - ( 2 , 5 - dimethoxy - 4 nylphenyl) ethanamine ) , 4 - TME ( aka 2 - ( 3 - ethoxy - 5 phenylsulfanylphenyl ) propan - 2 - amine ), ALEPH - 7 (aka methoxy - 4 -methylsulfanylphenylethanamine ), 4 - TSB ( aka 1- ( 2, 5 -dimethoxy -4 - propylsulfanylphenyl) propan -2 2 -( 3 ,5 -diethoxy -4 -methylsulfanylphenyl ) ethanamine ), amine) , ARIADNE (aka (2R ) - 1 -( 2 ,5 -dimethoxy - 4 -methyl 4T -MMDA - 2 (aka 1- (5 -methoxy - 1, 3 - benzoxathiol- 6 - yl) phenyl) butan - 2 -amine ), ASB (aka 2 -( 3 ,4 - diethoxy - 5 propan - 2 - amine ), 5 - TASB ( aka 2 - ( 3 ,4 - diethoxy - 5 -methyl methoxyphenyl) ethanamine ), B ( aka 2 - (4 -butoxy - 3 , 5 sulfanylphenyl ) ethanamine ) , 5 - TME ( aka 2 - ( 3 - ethoxy - 4 dimethoxyphenyl) ethanamine ) , BEATRICE ( aka 1 - ( 2 , 5 methoxy - 5 -methylsulfanylphenyl ) ethanamine ), 5 - TOET dimethoxy - 4 -methylphenyl ) - N -methylpropan -2 - amine ) , (aka 1 - (4 - ethyl- 2 -methoxy - 5 -methylsulfanylphenyl ) propan beta - D (aka 2 , 2 - dideuterio - 2 -( 3 ,4 ,5 - trimethoxyphenyl) 2 - amine ) , 5 - TOM (aka 1 - ( 2 -methoxy - 4 -methyl - 5 -methyl ethanamine ) , BIS - TOM ( aka 1 - [ 4 -methyl - 2 , 5 - bis( methyl sulfanylphenyl ) propan - 2 - amine ), 25B -NBF ( aka 2 - ( 4 sulfanyl) phenyl ] propan - 2 -amine ), bk - 2C - B ( aka 2 - amino - 1 bromo- 2 , 5 - dimethoxyphenyl) - N - [ ( 2 - fluorophenyl) methyl ] ( 4 -bromo - 2 ,5 -dimethoxyphenyl ) ethanone ), BOB ( aka 2 -( 4 ethanamine ), 25B -NBOH (aka 2 - [[ 2 -( 4 -bromo - 2 ,5 bromo - 2 , 5 - dimethoxyphenyl) - 2 -methoxyethanamine ) , dimethoxypheny )ethylaminolmethyl ] phenol ), 25B -NBOMe BOD (aka 2 -( 2 ,5 -dimethoxy - 4- methylphenyl ) - 2 -methoxy ( aka 2 - ( 4 - bromo- 2 , 5 - dimethoxyphenyl) - N [ ( 2 -methoxyphe ethanamine ), BOH ( aka 2 - ( 1 , 3 -benzodioxol - 5 - yl) - 2 nyl) methyl ] ethanamine ), 25C - NB30Me ( aka 2 - ( 4 - chloro - 2 , methoxyethanamine ), BOHD ( aka 2 - amino - 1 - ( 2 , 5 - dime 5 - dimethoxyphenyl) - N - [ ( ( 3 -methoxypheny )methyl ] ethan thoxy - 4 -methylphenylethanol ) , BOM ( aka 2 -methoxy - 2 - ( 3 , amine ) , 25C -NB40Me (aka 2 - ( 4 - chloro - 2 , 5 4 , 5 - trimethoxyphenyl) ethanamine) , bromo -dragonFLY ( aka US 2019 /0142851 A1 May 16 , 2019

1 -( 4 -bromofuro [2 ,3 - f] [ 1 ]benzofuran - 8 -yl ) propan - 2 -amine ), benzodioxol- 5 -yl )- N -benzylpropan -2 - amine ), MDCPM butylone (aka 1 - ( 1 , 3 -benzodioxl - 5 -yl ) - 2 - (methylamino )bu ( aka 1 - ( 3a ,7a - dihydro - 1 , 3 -benzodioxol - 5 - yl) - N - ( cyclopro tan - 1 - one ), CPM (aka 2 - [ 4 - ( cyclopropylmethoxy ) - 3 , 5 - di pylmethyl) propan - 2 - amine ) , MDDM (aka 1 - ( 1, 3 -benzodi methoxyphenyl] ethanamine ), DESOXY (aka 2 - ( 3 , 5 - dime oxol- 5 - yl) - N , N - dimethylpropan - 2 - amine ), MDE ( aka 1 - ( 1 , thoxy - 4 -methylpheny ) ethanamine ), DMCPA (aka 2 -( 2 , 5 3 -benzodioxol -5 - yl) -N - ethylpropan - 2 - amine ), MDHOET dimethoxy - 4 -methylphenyl ) cyclopropan - 1 -amine ), DME (aka 2 -[ 1- ( 1, 3 -benzodioxol - 5 -yl ) propan - 2 -ylamino )etha ( aka 2 - amino - 1 - ( 3 , 4 - dimethoxyphenyl) ethanol ), DMMDA nol) , MDIP (aka 1 -( 1, 3 -benzodioxol - 5 - yl) - N -propan - 2 -yl (aka 1 - ( 4 , 7 - dimethoxy - 1 , 3 -benzodioxol - 5 -yl ) propan - 2 propan - 2 - amine ), MDMA ( aka 1 - ( 1 , 3 -benzodioxol - 5 - yl ) - N amine ), DMMDA - 2 (aka 1- 6 , 7 -dimethoxy - 1, 3 -benzodi methylpropan - 2 - amine ), MDMC ( aka 1 - ( 2 , 3 - dihydro - 1 , 4 oxol - 5 - yl) propan - 2 - amine ) , DMPEA ( aka 2 - ( 3 , 4 - dime benzodioxin -6 -yl ) - N -methylpropan - 2 -amine ), MDMEO thoxyphenyl) ethanamine) , DOAM ( aka 1 - ( 2 , 5 - dimethoxy (aka 1 - ( 1, 3 -benzodioxol - 5 - yl) - N -methoxypropan - 2 - amine ), 4 -pentylphenyl ) propan - 2 - amine ) , DOB ( aka 1 - ( 4 -bromo - 2 , MDMEOET ( aka 1 -( 1 , 3 -benzodioxol - 5 - yl ) - N - ( 2 -methoxy 5 -dimethoxyphenyl ) propan - 2 - amine ) , DOBU ( aka 1- (4 ethyl) propan - 2- amine ) , MDMP ( aka 1 -( 1 ,3 -benzodioxol - 5 butyl- 2 ,5 -dimethoxyphenyl ) propan - 2 -amine ) , DOC (aka yl) -N ,2 -dimethylpropan - 2 -amine ), MDOH ( aka N -[ 1 -( 1, 3 1 - ( 4 - chloro - 2 , 5 -dimethoxyphenyl ) propan - 2 - amine ), DOEF benzodioxol- 5 -yl ) propan - 2 -yl ] hydroxylamine ) , MDPEA (aka 1 -[ 4 -( 2 - fluoroethyl) - 2 ,5 -dimethoxyphenyl ] propan - 2 (aka 2 - ( 1 , 3 -benzodioxol - 5 -yl ) ethanamine ) , MDPH (aka amine ), DOET (aka 1 - ( 4 - ethyl- 2 , 5 - dimethoxyphenyl) pro 1 -( 1 , 3 -benzodioxol - 5 - yl) - 2 -methylpropan - 2 - amine ), MDPL pan -2 -amine ), DOF (aka 1 - (4 - fluoro - 2 ,5 -dimethoxyphenyl ) (aka 1 - ( 1 , 3 - benzodioxol- 5 - yl) - N - prop - 2 - ynylpropan - 2 propan - 2 -amine ), DOI (aka 1 -( 4 - iodo -2 , 5 amine ), MDPR (aka 1 - ( 1 , 3 -benzodioxol - 5 - yl) - N -propylpro dimethoxyphenyl) propan -2 -amine ), DOM (aka 1 - (2 , 5 pan - 2 -amine ) , ME ( aka 2 - ( 3 - ethoxy - 4 , 5 -dimethoxyphenyl ) dimethoxy -4 -methylphenyl ) propan - 2 - amine ), DON ( aka ethanamine) , MEDA (aka 1- (5 -methoxy - 2 ,3 -dihydro - 1, 4 1 -( 2 , 5 -dimethoxy - 4 - nitrophenyl) propan - 2 - amine ) , DOPR benzodioxin - 7 - yl) propan - 2 - amine) , MEE ( aka 1 - ( 4 , 5 ( aka 1 - ( 2 , 5 -dimethoxy -4 - propylphenyl) propan - 2 - amine ), diethoxy - 2 - methoxyphenyl ) propan - 2 - amine ) , MEM ( aka DOTFM (aka 1 - [ 2 , 5 -dimethoxy - 4 - ( trifluoromethyl) phenyl] 1 - ( 4 - ethoxy - 2 , 5 -dimethoxyphenyl ) propan - 2 - amine ) , propan - 2 - amine ), E ( aka 2 - ( 4 - ethoxy - 3 , 5 - dimethoxyphenyl) MEPEA ( aka 2 -( 4 - ethoxy -3 -methoxyphenyl ) ethanamine ), ethanamine ), EBDP (aka 1 - ( 1, 3 - benzodioxol- 5 - yl) -N - ethyl META -DOB (aka 1 -( 5 -bromo -2 , 4 -dimethoxyphenyl ) pro pentan - 2 - amine ) , EEE (aka 1 - ( 2 , 4 , 5 - triethoxyphenyl) pan - 2 -amine ) , META -DOT (aka 1 - ( 2 ,4 - dimethoxy - 5 -meth propan - 2 -amine ), EEM (aka 1- ( 2 ,4 -diethoxy - 5 ylsulfanylphenyl) propan - 2 -amine ), METHYL - DMA ( aka methoxyphenyl) propan - 2 - amine ), EME ( aka 1 - ( 2 , 5 1 -( 2 , 5 -dimethoxyphenyl ) - N -methylpropan - 2 - amine ), diethoxy - 4 -methoxyphenyl ) propan - 2 - amine ), EMM ( aka METHYL - DOB (aka 1 - ( 4 - bromo - 2 , 5 -dimethoxyphenyl ) - N 1 - ( 2 - ethoxy - 4 , 5 - dimethoxyphenyl) propan - 2 -amine ) , methylpropan - 2 - amine ), METHYL - J ( aka 1 - ( 1 , 3 - benzodi ETHYL - J (aka 1 - ( 1 , 3 - benzodioxol - 5 - yl) - N - ethylbutan - 2 oxol- 5 -yl ) - N -methylbutan - 2 -amine ), METHYL - K ( aka amine ), ETHYL - K ( aka 1 - ( 1 , 3 -benzodioxol - 5 - yl) - N - ethyl 1 - ( 1 , 3 - benzodioxol - 5 -yl ) - N -methylpentan - 2 -amine ) , pentan - 2 - amine ), F - 2 (aka 1 - ( 5 -methoxy - 2 -methyl - 2 , 3 - di METHYL -MA (aka 1 - (4 -methoxyphenyl )- N -methylpropan hydro - 1 -benzofuran - 6 -yl ) propan - 2 - amine ) , F - 22 (aka 1 - ( 5 2 -amine ) , METHYL -MMDA - 2 (aka 1 - (6 -methoxy - 1 , 3 -ben methoxy - 2 , 2 - dimethyl -3H - 1 -benzofuran - 6 - yl) propan - 2 zodioxol- 5 -yl ) - N -methylpropan - 2 - amine ) , MMDA ( aka amine ), FLEA (aka N - [ 1 - ( 1 , 3 - benzodioxol - 5 - yl) propan - 2 1 -( 7- methoxy -1 ,3 -benzodioxol - 5 -yl ) propan - 2 -amine ), yl] - N -methylhydroxylamine ) , G - 3 ( aka 1 - ( 4 , 7 -dimethoxy - 2 , MMDA - 2 ( aka 1 - ( 6 -methoxy - 1 , 3 - benzodioxol- 5 - yl) propan 3 - dihydro - 1H - inden - 5 -yl ) propan - 2 - amine ) , G - 4 ( aka 1 - ( 1 , 4 2 - amine ), MMDA - 3a (aka 1 -( 4 -methoxy - 1 , 3 - benzodioxol dimethoxy - 5 , 6 , 7 , 8 - tetrahydronaphthalen - 2 - yl) propan - 2 5 -yl ) propan - 2 -amine ), MMDA - 3b ( aka 1- ( 7 -methoxy - 1, 3 amine ) , G - 5 (aka 3 , 6 -dimethoxy - 4 - ( 2 - aminopropyl) benzodioxol- 4 - yl) propan - 2 - amine ) , MME ( aka 1 - ( 5 - ethoxy benzonorbornane ) , G - N ( aka 1 - ( 1 , 4 - dimethoxynaphthalen 2 , 4 - dimethoxyphenyl) propan - 2 - amine ) , MP (aka 2 - ( 3 , 4 2 - yl) propan - 2 - amine ) , GANESHA ( aka 1 - ( 2 , 5 - dimethoxy dimethoxy - 5 - propoxyphenyl ) ethanamine ), MPM ( aka 1 - ( 2 , 3 ,4 -dimethylphenyl ) propan - 2 -amine ), HOT -17 (aka N -[ 2 4 -dimethoxy - 5 -propoxyphenyl ) propan - 2 - amine) , NBOMe ( 4 -butan -2 - ylsulfanyl- 2 ,5 - dimethoxypheny ) ethyl] mescaline (aka N - [( 2 -methoxyphenyl )methyl )- 2 -( 3 ,4 , 5 hydroxylamine ), HOT- 2 ( aka N - [ 2 - ( 4 -ethylsulfanyl - 2 , 5 trimethoxypheny ) ethanamine ) , ORTHO -DOT (aka 1 - ( 4 , 5 dimethoxypheny )ethyl ]hydroxylamine ), HOT- 7 (aka N -[ 2 dimethoxy - 2 -methylsulfanylphenyl ) propan - 2 -amine ) , P ( 2, 5 - dimethoxy -4 -propylsulfanylpheny )ethyl ] ( aka 2 - ( 3 , 5 - dimethoxy - 4 - propoxyphenyl ) ethanamine ) , PE hydroxylamine ), IDNNA ( aka 1 - ( 4 - iodo - 2 ,5 ( aka 2 - [ 3 , 5 - dimethoxy -4 - ( 2 - phenylethoxy ) phenyl] ethan dimethoxyphenyl) - N , N -dimethylpropan -2 -amine ), IM (aka amine ), PEA (aka 2 - phenylethanamine ), PROPYNYL (aka 2 -( 2 , 3 ,4 -trimethoxyphenyl ) e thanamine ), IP (aka 2 -( 3, 5 -di 2 -( 3 ,5 -dimethoxy -4 -prop -2 - ynoxyphenyl) ethanamine ), psi methoxy - 4- propan -2 -yloxyphenyl ) ethanamine ), IRIS ( aka 2C - T - 4 , psi -DOM ( aka 1 - ( 2 ,6 -dimethoxy - 4 -methylphenyl ) 1 - ( 5 - ethoxy - 2 -methoxy - 4 -methylphenyl ) propan - 2 - amine) , J propan - 2 - amine ), SB ( aka 2 - ( 3 , 5 -diethoxy - 4 -methoxyphe ( aka 1 - ( 1, 3 - benzodioxol- 5 -yl ) butan -2 - amine ), jimscaline nyl) ethanamine ) , TA (aka 1 - ( 2 , 3 , 4 , 5 - tetramethoxyphenyl) (aka [ (1R ) - 4 , 5 ,6 - trimethoxy - 2 , 3 -dihydro - 1H - inden - 1 - yl] propan -2 - amine ) , TB (aka 2 - ( 4 -butylsulfanyl - 3, 5 methanamine ) , LOPHOPHINE (aka 2 - ( 7 -methoxy - 1 , 3 - ben dimethoxyphenylethanamine ) , TCB - 2 ( aka ( 3 -bromo - 2 , 5 zodioxol- 5 - yl )ethanamine ) , M (aka 2 - ( 3 , 4 , 5 - trimethoxy dimethoxy - 7 - bicyclo [ 4 . 2 .0 ] octa - 1 ( 6 ) , 2 ,4 -trienyl ) phenylethanamine ), MADAM - 6 (aka N -methyl - 1 -( 6 methanamine ;hydrobromide ), TMA ( aka 1 - ( 3 ,4 , 5 methyl- 1 , 3 -benzodioxol - 5 -yl ) propan - 2 - amine ) , MAL ( aka trimethoxyphenyl) propan -2 - amine ), TMA - 2 (aka 1 -( 2, 4, 5 2 - [ 3, 5 -dimethoxy -4 -( 2 -methylprop - 2 -enoxy )phenyl ] ethan trimethoxyphenyl) propan - 2 - amine ) , TMA - 3 (aka 1 - ( 2 , 3 ,4 amine ), MDA ( aka 1 - ( 1 , 3 -benzodioxol - 5 - yl) propan - 2 trimethoxyphenyl) propan - 2 - amine ) , TMA - 4 ( aka 1 - ( 2 , 3 , 5 amine ), MDAL (aka 1 -( 1, 3 -benzodioxol - 5 -yl ) - N -prop - 2 trimethoxyphenyl) propan - 2 - amine) , TMA - 5 ( aka 1 - ( 2 , 3 , 6 enylpropan - 2 - amine ), MDBU ( aka N - [ 1 - ( 1 , 3 -benzodioxol trimethoxyphenyl) propan - 2 - amine) , TMA - 6 ( aka 1 - ( 2 ,4 , 6 5 -yl ) propan - 2 -yl ] butan - 1 - amine ), MDBZ (aka 1- (1 ,3 trimethoxyphenyl) propan - 2- amine ) , TMPEA (aka 2 -( 2, 4, 5 US 2019 /0142851 A1 May 16 , 2019 29 trimethoxyphenyl ) ethanamine ), TOMSO ( aka 1 - ( 2 In one embodiment, an adrenergic drug binds to an adren methoxy - 4 - methyl- 5 -methylsulfinylphenyl ) propan - 2 ergic receptor. In one embodiment, an adrenergic drug amine ) , TP ( aka 2 - ( 3 , 5 - dimethoxy - 4 - propylsulfanylphenyl) indirectly affects an adrenergic receptor, e .g . , via interac ethanamine ), and TRIS (aka 2 - (3 , 4 ,5 - triethoxyphenyl) tions affecting the reactivity of other molecules at the ethanamine ). For additional information regarding these adrenergic receptor. In one embodiment , an adrenergic drug compounds, see Shulgin , A . T ., & Shulgin , A . ( 2016 ) . is an agonist , e . g. , a compound activating an adrenergic Tihkal: The Continuation . Berkeley , Calif. : Transform Press . receptor. In one embodiment, an adrenergic drug is an [ 0311 ] In one embodiment, a serotonergic drug is chosen antagonist , e . g ., a compound binding but not activating an from alprazolam , amphetamine , aripiprazole , azapirone , a adrenergic receptor, e . g . , blocking a receptor. In one embodi barbiturate , bromazepam , bupropion , buspirone , a cannabi ment, an adrenergic drug is an effector molecule , e . g . , a noid , chlordiazepoxide , citalopram , clonazepam , clora compound binding to an enzyme for allosteric regulation . In zepate , dextromethorphan , diazepam , duloxetine , escitalo one embodiment , an adrenergic drug acts ( either directly or pram , fluoxetine, flurazepam , fluvoxamine, lorazepam , indirectly ) at more than one type of receptor ( e .g . , 5HT, lysergic acid diethylamide, lysergamide, 3 , 4 -methylenedi dopamine , adrenergic , acetylcholine, etc . ). oxymethamphetamine , milnacipran , mirtazapine, naratrip tan , paroxetine , pethidine , phenethylamine, psicaine , oxaze [0317 ] In one embodiment, an adrenergic drug is an anti pam , reboxetine , serenic , serotonin , sertraline, temazepam , depressant. tramadol, triazolam , a tryptamine , venlafaxine , vortioxetine , [0318 ] In one embodiment, an adrenergic drug is a nor and / or derivatives thereof. epinephrine transporter inhibitor. [ 0312] As used herein , the term “ serotonin ” refers to a [0319 ] In one embodiment , an adrenergic drug is a vesicu neurotransmitter compound with the following structural lar monoamine transporter inhibitor. formula : [0320 ] In one embodiment, an adrenergic drug is chosen from adrenaline , agmatine , amoxapine, aptazapine , atomox etine , bupropion , clonidine , doxepin , duloxetine , esmirtaz pine , mianserin , mirabegron , mirtazapine , norepinephrine , N - H . phentolamine , phenylephrine , piperoxan , reserpine , rito drine , setiptiline , tesofensine, timolol, trazodone , trimip ramine , or xylazine . [ 0321] As used herein , the term “ adrenaline” , also known as " epinephrine ” , refers to a neurotransmitter compound with the following structural formula :

OH [ 0313 ] In one embodiment, serotonin acts at a serotonin receptor , e . g . , by acting as a ligand at a 5 -HT receptor. In one ?? , embodiment, serotonin is produced by an organism for use as a neurotransmitter within that organism . In one embodi ment, the compositions disclosed herein increase the activity HO at a serotonin receptor . In one embodiment, the composi tions disclosed herein decrease the activity at a serotonin receptor. [0322 ] In one embodiment, adrenaline acts at an adrener [0314 ] As used herein , the term " serotonin receptor ” refers gic receptor, e .g ., by acting as a ligand at an adrenergic to a collection of proteins outside a cell capable of receiving receptor. In one embodiment, adrenaline is produced by an signals and activating internal signal transduction pathways organism for use as a neurotransmitter within that organism . causing a cellular response . In one embodiment, a serotonin In one embodiment, the compositions disclosed herein receptor is found on a cell within the central nervous system increase the activity at an adrenergic receptor. In one of an organism . In one embodiment, a serotonin receptor is embodiment, the compositions disclosed herein decrease the found on a cell within the peripheral nervous system of an activity at an adrenergic receptor. organism . In one embodiment, serotonin is the natural ligand [ 0323 ] As used herein , the term “ adrenergic receptor ” for a serotonin receptor. In one embodiment, a serotonin refers to a collection of proteins outside a cell capable of receptor modulates the release of a neurotransmitter , e .g ., receiving signals and activating internal signal transduction glutamate, gamma - Aminobutyric acid , dopamine , epineph pathways causing a cellular response . In one embodiment, rine ( a . k . a . norepinephrine ) , acetylcholine , etc . In one an adrenergic receptor is found on a cell within the central embodiment, a serotonin receptor modulates the release of a nervous system of an organism . In one embodiment, an hormone , e . g ., oxytocin , prolactin , vasopressin , cortisol, adrenergic receptor is found on a cell within the sympathetic corticotropin , substance P , etc . nervous system of an organism . [ 0315 ] Examples of serotonin receptors include , but are not limited to , 5 -HT 14 , 5 -HT1B , 5 - HT10 , 5 -HT1E , 5 -HT2A , [0324 ] Examples of adrenergic receptors include, but are 5 -HT2B , 5 -HT2C , 5 -HT3 , 5- HT4 , 5 -HT3A , 5 -HT3B , 5 -HT6 , not limited to , a A , a B , a D , A2A , a B , a C , B1, B2, and and 5 -HT7 . Bz: [ 0316 ] As used herein , the term “ adrenergic drug” refers to [0325 ] As used herein , the term “ norepinephrine” refers to a compound that binds , blocks , or otherwise influences ( e . g . , a neurotransmitter compound with the following structural via an allosteric reaction ) activity at an adrenergic receptor. formula : US 2019 /0142851 A1 May 16 , 2019

activity at a dopamine receptor. In one embodiment , the OH compositions disclosed herein decrease the activity at a dopamine receptor. HO NH2. [0333 ] As used herein , the term “ dopamine receptor " refers to a collection of proteins outside a cell capable of receiving signals and activating internal signal transduction HO pathways causing a cellular response . In one embodiment , a dopamine receptor is found on a cell within the central [0326 ] In one embodiment, norepinephrine acts at an nervous system of an organism . adrenergic receptor, e . g . , by acting as a ligand at an adren [0334 ] Examples of dopamine receptors include , but are ergic receptor . In one embodiment , norepinephrine is pro not limited to , D1, D2, D25 D2h , D3, D4, and Ds. duced by an organism for use as a neurotransmitter within [0335 ] In one embodiment, a first purified terpene modu that organism . In one embodiment, the compositions dis lates the activity of a neurotransmitter at its native receptor , closed herein increase the activity at an adrenergic receptor. e . g . , serotonin at a serotonin receptor, dopamine at a dop In one embodiment, the compositions disclosed herein aminergic drug , norephedrine at an adrenergic receptor, etc . decrease the activity at an adrenergic receptor. [0336 ] In one embodiment, a first purified terpene is active [ 0327 ] As used herein , the term “ dopaminergic drug” at one or more receptors , e . g . , a serotonin receptor , an refers to a compound that binds , blocks , or otherwise adrenergic receptor, a dopamine receptor, a GABAergic influences ( e . g . , via an allosteric reaction activity at a receptor, a glutaminergic receptor, a histaminergic receptor , dopamine receptor. In one embodiment, a dopaminergic a cholinergic receptor, an opioid receptor, or a glycinergic drug binds to a dopamine receptor. In one embodiment, a receptor. dopaminergic drug indirectly affects a dopamine receptor , [0337 ] In one embodiment, the methods and compositions e . g ., via interactions affecting the reactivity of other mol disclosed herein comprise an excipient . ecules at the dopamine receptor. In one embodiment , a [0338 ] As used herein , the term “ excipient” refers to a dopaminergic drug is an agonist , e . g . , a compound activating compound useful for increasing the bioavailability of an a dopamine receptor . In one embodiment, a dopaminergic active ingredient or ingredients . In one embodiment, an drug is an antagonist, e . g . , a compound binding but not excipient allows for quicker absorption of an active ingre activating a dopamine receptor , e . g ., blocking a receptor. In dient into a human body. In one embodiment, an excipient one embodiment, a dopaminergic drug is an effector mol binds to a compound thereby providing faster permeability ecule , e . g . , a compound binding to an enzyme for allosteric across membranes , barriers , walls , etc . In one embodiment, regulation . In one embodiment, a dopaminergic drug acts the methods disclosed herein comprise administering two or ( either directly or indirectly ) at more than one type of more excipients , e. g ., a pH buffer , an antioxidant, etc . In one receptor ( e .g . , 5HT , dopamine , adrenergic , acetylcholine , embodiment, an excipient also functions as a stabilizer. In one embodiment, an excipient binds two or more com etc . ) . pounds forming a homogeneous mixture within a solution , [ 0328 ] In one embodiment , a dopaminergic drug is a e .g ., a purified water- insoluble compound ( e. g ., a cannabi dopamine transporter inhibitor. noid or terpene ) and a purified psilocybin derivative (water [0329 ] In one embodiment, a dopaminergic drug is a soluble ) forming a homogeneous mixture in water. vesicular monoamine transporter inhibitor. [03391 Examples of excipients are , but are not limited to , [ 0330] In one embodiment , a dopaminergic drug is chosen sodium lauryl sulfate , sucrose , alcohol , gelatin , polyvi from amineptine , apomorphine , benzylpiperazine, bro nylpyrrolidone , methionine, Vitamin E TPGS, dimethyl sul mocriptine , cabergoline , chlorpromazine , clozapine , dihy foxide , tartrazine , polyethylene glycol, magnesium stearate , drexidine , domperidone , dopamine , fluphenazine, haloperi stearic acid , fumed silica , talc, magnesium carbonate , or dol, ketamine, loxapine, methamphetamine , olanzapine , benzalkonium chloride. pemoline , perphenazine, pergolide, phencyclidine , pheneth [0340 ] In one embodiment, the compositions disclosed ylamine , phenmetrazine , pimozide, piribedil, a psycho herein comprise a monoamine oxidase inhibitor . stimulant, reserpine , risperidone, ropinirole , tetrabenazine , [0341 ] As used herein , the term “monoamine oxidase or thioridazine . inhibitor ” refers to a molecule binding to a monoamine oxidase enzyme thereby reducing the activity of the mono [0331 ] As used herein , the term “ dopamine” refers to a amine oxidase enzyme. Within the context of this disclosure , neurotransmitter compound with the following structural examples of monoamine oxidase inhibitors include aurorix , formula : deprenyl , eldepryl, emsam , humoryl, hydracarbazine, iso carboxazid , linezolid , manerix , nydrazid , phenelzine , pirazi ?? . NH2. dol, procarbazine , rasagiline, and tranylcypromine . In one embodiment, monoamine oxidase catalyzes the oxidation of a monoamine, e . g . , serotonin , dopamine, norepinephrine , ?? . amphetamine, adrenaline , etc . [0342 ] In one embodiment, the methods and compositions disclosed herein comprise a stabilizer. As used herein , the [ 0332] In one embodiment , dopamine acts at a dopamine term “ stabilizer” refers to a compound useful for preventing receptor, e. g ., by acting as a ligand at a dopamine receptor. the degradation of an active ingredient, e . g ., a psilocybin In one embodiment , dopamine is produced by an organism derivative , a cannabinoid , a terpene , etc . In one embodi for use as a neurotransmitter within that organism . In one ment, a stabilizer prevents a first psilocybin derivative from embodiment, the compositions disclosed herein increase the degrading . In one embodiment, a stabilizer prevents a first US 2019 /0142851 A1 May 16 , 2019 31 psilocybin derivative from reacting with other compounds in [0357 ] In one embodiment , a pH buffer comprises citric the composition , e . g. , a cannabinoid , a terpene, a base, an acid , acetic acid , monosodium phosphate , N -Cyclohexyl - 2 acid , etc . In one embodiment, a stabilizer prevents a first aminoethanesulfonic acid , borate, hydrochloric acid , and /or psilocybin derivative from reacting with the ambient atmo sodium hydroxide . sphere , e . g . , heat, light, water , and / or oxygen . In one [0358 ] In one embodiment, the methods disclosed herein embodiment, a stabilizer comprises an antioxidant. In one comprise administering a formulation comprising an acid . embodiment, a stabilizer comprises a pH buffer. [0359 ] As used herein , the term “ acid ” refers to a molecule [0343 ] In one embodiment, the methods and compositions orion capable of donating a proton , i. e ., H * and / or accepting disclosed herein comprise an antioxidant. As used herein , electrons. In one embodiment, an “ acid ” refers to a Lewis the term " antioxidant ” refers to a compound and / or a com acid . In one embodiment, an " acid ” refers to a Bronsted acid . position useful for preventing oxidation . In one embodi In one embodiment, an acid is determined by a compositions ment, an antioxidant protects an active ingredient from “ free pH . In one embodiment, a pH below 7 indicates the presence radicals " . Within the context of this disclosure , a “ free of an acid . radical” is an atom , molecule, or an ion with an unpaired 10360 ] In one embodiment, the compositions and methods valence electron . In one embodiment, an antioxidant is an disclosed herein comprise administering a formulation com electron donor . prising a base . 10344 ] In one embodiment , an antioxidant is chosen from [0361 ] As used herein , the term “ base” refers to a mol ascorbic acid , lycopene, tocopherol, melatonin , retinol, ecule or ion capable of accepting a proton , i. e . , an H + . In one astaxanthin , lutein , apigenin , carnosine , selenium , zinc , embodiment, a " base ” refers to a molecule capable of cucurmin , and / or a salt or derivative thereof. donating an electron pair, i . e ., a Lewis base. In one embodi [0345 ] In one embodiment, an antioxidant is ascorbic acid ment, the presence of a base is determined by a compound ' s and / or its salts or derivatives . Within the context of this pH . In one embodiment, a pH above 7 indicates the presence disclosure, the term “ ascorbic acid ” comprises Vitamin C of a base . and / or a salt or derivative thereof. [ 0362 ] In one embodiment , the compositions and methods [ 0346 ] In one embodiment, an antioxidant prevents the disclosed herein comprise administering a water - soluble oxidation of a composition comprising one or more com composition . pounds disclosed herein , e . g ., psilocybin derivatives , can [0363 ] As used herein , the term “ water soluble ” refers to nabinoids , terpenes , and / or mixtures thereof . For example , a compound capable of dissolving in water at standard preventing the oxidation of a phenolic group attached to a temperature and pressure . In one example , 1 g of a com psilocybin derivative . pound dissolves in 1 L of water. In one example, 2 g of a [ 0347 ] As used herein , the term " oxidation ” refers to the compound dissolves in 1 L of water . In one example , 5 g of formal loss of electrons and / or the increase of the formal a compound dissolves in 1 L of water. In one example , 10 oxidation state and /or the addition of an oxygen atom or g of a compound dissolves in 1 L of water . In one embodi atoms. “ Reduction ” refers to the formal gain of electrons ment, a compound 's solubility in water is an inherent and / or the decrease of the formal oxidation state . Zumdahl, property of a compound . In one embodiment , a compound ' s Steven S . , et al . Chemistry , 7th . Cengage Learning , 2018 . solubility in water is facilitated by another compound , e . g . , [ 0348 ] In one embodiment, an antioxidant prevents the an excipient. oxidation of a composition comprising one or more com [0364 ] In one embodiment, the compositions and methods pounds disclosed herein , e . g . , psilocybin derivatives or disclosed herein comprise a solvent. mixtures thereof In one embodiment, the methods and [ 0365 ] As used herein , the term “ solvent” refers to a compositions disclosed herein comprise a pH buffer . compound or composition that discloses another ( a solute ) , [ 0349] As used herein , the term “ pH buffer ” refers to a thereby creating a solution . In one embodiment, the solvent compound or a composition useful for maintaining the pH of is water. In one embodiment, the solvent is an oil . In one a composition . In one embodiment, a pH buffer comprises a embodiment, the solvent is an alcohol. weak acid and a corresponding conjugate base . In one [036 ] In one embodiment, the compositions and methods embodiment, a pH buffer comprises a weak base and a disclosed herein comprise administering a first purified corresponding conjugate acid . In one embodiment, a pH buffer does not change the pH of a composition with the psilocybin derivative present as and /or within a homogenous addition of a strong acid and /or base . mixture within a first dosage formulation . [ 0350 ] In one embodiment, a pH buffer maintains the pH [0367 ] In one embodiment, the compositions and methods of a composition around 7 . disclosed herein comprise administering a first purified [0351 ] In one embodiment, a pH buffer maintains the pH psilocybin derivative and a first purified cannabinoid present of a composition below 7 . as and / or within a homogenous mixture within a first dosage formulationMulation . [0352 ] In one embodiment, a pH buffer maintains the pH 10368 ] In one embodiment , the compositions and methods of a composition above 7 . disclosed herein comprise administering a first purified [ 0353] In one embodiment, a pH buffer maintains the pH psilocybin derivative and a first purified terpene present as of a composition between 2 - 6 . and / or within a homogenous mixture within a first dosage [0354 ] In one embodiment, a pH buffer maintains the pH formulation . of a composition between 5 - 7. [0369 ] In one embodiment, the compositions and methods [0355 ] In one embodiment, a pH buffer maintains the pH disclosed herein comprise administering a first purified of a composition between 6 - 8 . psilocybin derivative , a first purified cannabinoid , and a first [0356 ] In one embodiment, a pH buffer maintains the pH purified terpene present as and /or within a homogenous of a composition between 7 - 10 . mixture within a first dosage formulation . US 2019 /0142851 A1 May 16 , 2019 32

[0370 ] In one embodiment, the compositions and methods [0379 ] Moreover , the concentrations of molecules within disclosed herein comprise administering a first purified different samples may change at different rates because of psilocybin derivative , a first purified cannabinoid , a first degradation , such as oxidative degradation and /or enzymatic purified terpene , and an excipient present as and /or within a degradation . homogenous mixture within a first dosage formulation . [0380 ] As an advance beyond the state of the art, the [0371 ] As used herein , the term “ homogeneous mixture ” methods disclosed herein comprise administering composi refers to a solid , liquid , or gaseous composition that has two tions showing little or no deviation between aliquots taken or more compounds present within one state or thing, e .g ., from a particular batch . This is in contrast to technology a clear , colorless solution . In one embodiment, the homo relying on fungal or plant extracts which are notoriously geneous mixtures disclosed herein have the same propor unreliable in terms of the identity of ingredients and their tion , concentration , and / or ratio of its components across concentrations. In one embodiment, a sample composition different samples . In one embodiment, the components in weighing 100 grams, each 1 - gram portion deviates in chemi the homogeneous mixture are in the same state of matter. In cal concentration by less than about 10 % as compared to the one embodiment, a homogeneous mixture comprises one or currently available technology , e . g . , extracts . In another more compounds within a solution , e . g . , a first psilocybin embodiment, a sample weighing 100 grams, each 1 - gram derivative and a first cannabinoid within a clear solution . In portion deviates in chemical concentration by less than one embodiment , the compositions disclosed herein are about 5 % as compared to the currently available technology . present as a homogenous mixture, e . g ., a solution with no In another embodiment, a sample weighing 100 grams, each particulates , a solution with equal concentrations across 1 - gram portion would deviate in chemical concentration of samples , a powder of similar particle size , etc . less than about 1 % as compared to the currently available [0372 ] In one embodiment, a homogeneous mixture is a technology . [0381 ] In one embodiment, the compositions and methods solution comprising a first purified psilocybin derivative . disclosed herein comprise a dephosphorylating agent. [0373 ] In one embodiment, a homogeneous mixture is a [ 0382 ] As used herein , the term “ dephosphorylating solution comprising a first purified psilocybin derivative and agent” refers to a compound or composition capable of a first purified cannabinoid . In one embodiment, a homoge facilitating the removal of a phosphate group from a mol neous mixture is a solution comprising a first purified ecule comprising a phosphate group . In one embodiment, a psilocybin derivative and a first purified terpene . dephosphorylating agent is kept physically separate (e . g. , a [0374 ] In one embodiment, a homogeneous mixture is a film , a coating , or other barrier preventing mixing ) from an solution comprising a first purified psilocybin derivative , a active ingredient, e . g ., a purified psilocybin derivative first purified cannabinoid , and a first purified terpene. within a composition . In one embodiment, a dephosphory [0375 ] In one embodiment, a homogeneous mixture has lating agent removes a phosphate group from a psilocybin little or no deviation in a chemical composition between derivative , e . g ., psilocybin . across different samples taken of the compositions disclosed [0383 ] In one embodiment, the methods disclosed herein herein . comprise dephosphorylating a psilocybin derivative. [ 0376 ] As used herein , the phrase " little or no deviation ” [0384 ] As used herein , the term “ dephosphorylating ” means that different samples from the same composition are refers to removing a phosphate group from a molecule internally consistent. For example , two different 1 g aliquots, having a phosphate group . In one embodiment, dephospho taken from the same 100 g sample , would have " little or no rylating a first purified psilocybin derivative comprises deviation ” when they share substantially the same chemical cleaving chemical bonds via hydrolysis . In one embodiment, composition when characterized by chromatography and/ or dephosphorylating a first purified psilocybin derivative spectrometry . By contrast, naturally occurring fungal fruit - changes ( e . g ., increase ) activity at one or more neurotrans ing bodies (aka mushrooms ) or plants often show consider mitter receptors . In one embodiment, dephosphorylating a able deviation in the chemical concentration of certain first purified psilocybin derivative occurs within an organ compounds. ism . In one embodiment, dephosphorylating a first purified [ 0377 ] For example , the concentration of psilocybin and / psilocybin derivative occurs before administering a compo or psilocin varies greatly across species of naturally occur sition . ring fungal fruiting bodies, e . g. , 0 to 15 mg of psilocybin [0385 ] Disclosed herein is a method of modulating activity and / or psilocin per gram of dry plant material. Stafford , at a neurotransmitter receptor , comprising: Peter. Psychedelics Encyclopedia : Third Expanded Edition . [0386 ] administering a neurotransmitter activity modu Ronin Publishing , 1993 . Likewise , extracts taken from these lator ; and highly variable samples are similarly variable . [ 0387 ] administering a first dosage formulation com [0378 ] The concentration of psilocybin and / or psilocin prising a first purified psilocybin varies greatly between species and even between specimens [0388 ] derivative to the person in need of treatment, of a species collected and /or grown from the same culture . wherein the first dosage formulation modulates activity at a Bigwood J , Beug MW ( 1982 ) . " Variation of psilocybin and neurotransmitter receptor. psilocin levels with repeated flushes (harvests ) of mature [0389 ] As used herein , the term “ modulating activity of sporocarps of Psilocybe cubensis ( Earle ) Singer " . Journal of the neurotransmitter activity modulator” refers to changing , Ethnopharmacology . 5 ( 3 ): 287 -91 . See also , U . S . Patent manipulating, and / or adjusting the ability of a compound or Application Publication No . US 20180021326 (disclosing composition to affect a neurotransmitter receptor. In one combinations of various mushroom and /or plant extracts in embodiment, modulating the activity of a neurotransmitter contrast to combinations of purified compounds , which can activity modulator comprises administering an agonist at a be consistently and reliably dosed ) . neurotransmitter receptor. In one embodiment, modulating US 2019 /0142851 A1 May 16 , 2019 33 the activity of a neurotransmitter activity modulator com embodiment, a neurotransmitter activity modulator is an prises administering an antagonist at a neurotransmitter agonist . In one embodiment, a neurotransmitter activity receptor . modulator is an antagonist . In one embodiment, a neu [0390 ] As used herein , the term " administering ” ( e . g ., rotransmitter activity modulator acts (either directly or indi administering a drug ) refers to dosing , treating, giving , rectly ) at more than one type of neurotransmitter receptor . and/ or providing . In one embodiment, administering a neu [0396 ] In one embodiment, a neurotransmitter activity rotransmitter activity modulator comprises providing a neu modulator is chosen from aripiprazole , bupropion , citalo rotransmitter activity modulator to an organism with a pram , clomipramine , dextroamphetamine , duloxetine , esci neurotransmitter receptor, e . g . , a human being . In one talopram , fluoxetine , fluvoxamine, milnacipran , mirtazap embodiment, administering a neurotransmitter activity ine , paroxetine, quetiapine, reboxetine , risperidone , modulator comprises providing a neurotransmitter activity sertraline , and venlafaxine . modulator along with a purified psilocybin derivative , e .g ., 10397 ] As used herein , the term “ first dosage formulation ” a formulation having each of a neurotransmitter activity refers to a compound or compounds selected for the pur modulator and a purified psilocybin derivative in a single poses of causing a reaction , effect , and / or result , e . g ., caus dosage . In one embodiment, administering a neurotransmit ing activity at a neurotransmitter receptor , reacting with ter activity modulator comprises applying a transdermal other compounds, enhancing the effects of other active composition , e . g . , applying a topical composition to the skin ingredients , inhibiting the biosynthesis of a compound , etc ., having each of a neurotransmitter activity modulator and a within an organism . In one embodiment, a first dosage purified psilocybin derivative. In one embodiment , admin formulation comprises a first purified psilocybin derivative . istering a neurotransmitter activity modulator comprises In one embodiment, a first dosage formulation comprises a giving a transmucosal preparation , e. g. , providing rapidly first purified cannabinoid . In one embodiment, a first dosage dissolving a tablet with an absorption enhancer having each formulation comprises a first purified terpene . In one of a neurotransmitter activity modulator and a purified embodiment, a first dosage formulation comprises a first psilocybin derivative . purified psilocybin derivative and a second purified psilo [0391 ] In one embodiment, the methods disclosed herein cybin derivative . In one embodiment, a first dosage formu comprise transmucosally administering a composition for lation comprises a first purified psilocybin derivative and a crossing a blood -brain barrier. first purified cannabinoid . In one embodiment, a first dosage [ 0392] As used herein , the term “ transmucosally admin formulation comprises a first purified psilocybin derivative istering ” refers to providing a compound by entering and a first purified terpene . In one embodiment, a first through , or across, a mucous membrane, e . g . , an oral admin dosage formulation comprises a first purified psilocybin istration of a composition . In one embodiment, transmu derivative , a first purified cannabinoid , and first purified cosally administering refers to delivering a drug via the terpene . In one embodiment, a first dosage formulation cavity between the cheek and gum , e . g ., a liquid composi comprises a first purified psilocybin derivative , and a neu tion , a fast dissolving tablet, a patch , etc . In one embodi ment, transmucosally administering refers to delivering a rotransmitter activity modulator. drug under the tongue, e. g . , a liquid composition , a fast [0398 ] In one embodiment, a second dosage formulation dissolving tablet , a patch , etc . In one embodiment, transmu comprises a first purified psilocybin derivative . In one cosally administering refers to delivering a drug via the embodiment , a second dosage formulation comprises a upper gastrointestinal system , e . g . , a sublingual formulation second purified psilocybin derivative . In one embodiment, a or liquid preparation with a permeation enhancer, a tablet, a second dosage formulation comprises a first purified can food product, etc . nabinoid . In one embodiment, a second dosage formulation [0393 ] In one embodiment, the methods disclosed herein comprises a first purified terpene . In one embodiment, a comprise transdermally administering a composition . second dosage formulation comprises a first purified psilo cybin derivative and a first purified cannabinoid . In one [ 0394 ] As used herein , the term " transdermally adminis embodiment , a second dosage formulation comprises a first tering ” refers to providing a compound by entering the blood purified psilocybin derivative and a first purified terpene . In or body through the dermis , or skin , of an organism . In one embodiment, transdermally administering comprises apply one embodiment, a second dosage formulation comprises a ing a composition to the skin of an organism , e . g . , applying first purified psilocybin derivative , a first purified cannabi a topical composition , applying a liquid composition , etc . In noid , and a first purified terpene . In one embodiment, a one embodiment, transdermally administering a composi second dosage formulation comprises a first purified psilo tion comprises applying a patch embedded with the com cybin derivative , and a neurotransmitter activity modulator . position to the skin of an organism . [0399 ] In one embodiment , the methods disclosed herein [ 0395 ] As used herein , the term “ neurotransmitter activity comprise administering a second dosage formulation . In one modulator” refers to a compound or composition that reacts embodiment, the methods disclosed herein comprise admin or influences activity at a neurotransmitter receptor, e . g. , a istering a third dosage formulation . In one embodiment, the serotonergic drug , an adrenergic receptor , a dopamine recep methods disclosed herein comprise administering a fourth tor, a GABAergic receptor, a glutaminergic receptor, a dosage formulation . In one embodiment, the methods dis histaminergic receptor, a cholinergic receptor, an opioid closed herein comprise administering more than four dosage receptor, or a glycinergic receptor, etc . In one embodiment, formulations . a neurotransmitter activity modulator binds on a neurotrans [ 0400 ] In one embodiment, the methods disclosed herein mitter receptor . In one embodiment, a neurotransmitter comprise administering one or more active ingredients , e . g . , activity modulator indirectly affects a neurotransmitter psilocybin derivatives , cannabinoids, terpenes , neurotrans receptor, e. g . , via interactions affecting the reactivity of mitter activity modulators, etc . , in a single dosage , e . g ., a other molecules at a neurotransmitter receptor. In one single tablet, a single composition , a single formulation , etc . US 2019 /0142851 A1 May 16 , 2019 34

[0401 ] In one embodiment, the methods disclosed herein [0411 ] As used herein , the term “ acute stress disorder " comprise administering one or more active ingredients , e. g ., refers to a condition developed after exposure to one or more psilocybin derivatives, cannabinoids , terpenes , neurotrans traumatic events . Examples of traumatic events include , but mitter activity modulators , etc ., in more than two doses, e . g . , are not limited to , exposure to war , rape or sexual violence , two or more tablets , two or more compositions , two or more a physical attack , a mugging , childhood physical or sexual formulations, etc . violence , kidnapping or being taken hostage, terrorist [0402 ] Disclosed herein is a method of treating a psycho attacks , torture , natural disasters , and/ or severe accidents . In logical problem , comprising: one embodiment, acute stress disorder occurs within a day of experiencing a traumatic event. In one embodiment, acute [0403 ] identifying a person in need of treatment ; and stress disorder occurs within three days of experiencing a [ 0404 ] administering a first purified psilocybin deriva traumatic event. In some instances, acute stress disorder tive to the person in need of treatment, occurs within a week of experiencing a traumatic event . In [0405 ] wherein the first purified psilocybin derivative some instances , acute stress disorder occurs within a month modulates activity at a neurotransmitter receptor. of experiencing a traumatic event. [0406 ]. As used herein , the term “ identifying a person in [0412 ] As used herein , the term “ anxiety due to another need of treatment” refers to analyzing , diagnosing , and /or medical condition ” refers to a condition wherein anxiety determining whether a person requires a composition modu symptoms are developed because of a physiological and lating the activity at a neurotransmitter receptor . In one psychological consequence of a non - related disease , injury , embodiment , identifying a person in need of treatment and /or illness , e. g. , an endocrine disease , a cardiovascular comprises diagnosing a person with a medical condition , disorder , respiratory illness , a metabolic disturbance , a neu e . g ., a neurological disorder , a chemical imbalance , a heredi rological illness , etc . tary condition , etc . In one embodiment, identifying a person [0413 ] As used herein , the term “ generalized anxiety dis in need of treatment comprises performing a psychiatric order ” refers to a condition of persistent and excessive evaluation . In one embodiment, identifying a person in need anxiety and worry about various domains , e . g. , work , of treatment comprises performing a blood test . In one school, social settings , etc ., that an individual finds difficult embodiment, identifying a person in need of treatment to control. In addition , the individual experiences physical comprises determining whether a person has a compulsive symptoms including restlessness , alertness , and/ or nervous disorder . In one embodiment, identifying a person in need of ness ; being easily fatigued , difficulty concentrating or mind treatment comprises self identifying as having a compulsive going blank , irritability , muscle tension , and sleep distur disorder . bance . [0407 ] As used herein , the term “ psychological disorder” [0414 ] As used herein , the term “ panic disorder ” refers to refers to a condition wherein a person exhibits a pattern of a condition wherein an individual experiences recurrent and behavioral and / or psychological symptoms that impact mul unexpected panic attacks. The individual is persistently tiple life areas and create distress for the person experienc concerned about having more panic attacks and changes his ing these symptoms. In one embodiment, a psychological or her behavior in maladaptive ways because of these panic disorder is caused by a genetic disorder. In one embodiment , attacks, e . g. avoidance of exercise, unfamiliar locations, new a psychological disorder is caused by a biological condition , people , etc . e . g ., excess hormone production , a lack of activity at a [ 0415 ] As used herein , the term “ panic attack ” refers to an neurotransmitter receptor , a lack of producing neurotrans abrupt surge of intense fear or intense discomfort that mitters , etc . In one embodiment, the neurotransmitter recep reaches a peak within a short period of time , e . g . , seconds , tor is a serotonin receptor. minutes , hours , etc . In some instances, a panic attack com [0408 ] In one embodiment, the psychological problem is prises a physical and /or cognitive symptom . Panic attacks an anxiety disorder. In one embodiment, the psychological may be predictable , such as in response to a typically feared problem is a depressive disorder . In one embodiment, the object or situation . In some instances , a panic attack occurs psychological problem is a compulsive disorder . In one for no apparent reason . embodiment, the psychological problem is characterized by 10416 ) As used herein , the term “ phobia ” refers to a neurodegeneration . condition of being fearful, anxious about, or avoidant of a [0409 ] As used herein , the term “ anxiety disorder ” refers circumscribed object and/ or situation . In some instances , a to a state of apprehension , uncertainty , and /or fear resulting phobia comprises a fear , anxiety , or avoidance that is from the anticipation of an event and / or situation . An anxiety induced by a situation to a degree that is persistent and out disorder can disrupt the physical and psychological func of proportion to the actual risk posed . Examples of phobias tions of a person . These disruptions can cause a small include , but are not limited to , a fear or anxiety of an animal, hindrance to a debilitating handicap for a person ' s everyday a natural environment, an injection - injury, etc . life . An anxiety disorder can cause a physiological symptom , 10417 ]. As used herein , the term “ post - traumatic stress e . g ., muscle tension , heart palpitations , sweating, dizziness , disorder ” refers to a condition developed after experiencing shortness of breath , etc . An anxiety disorder can also cause and /or witnessing a traumatic event or learning that a a psychological symptom , e .g ., fear of dying , fear of embar traumatic event has happened to a loved one . In some rassment or humiliation , fear of an event occurring , etc . instances, a person shows symptoms of post - traumatic stress 10410 ] In one embodiment, an anxiety disorder comprises disorder within a week of experiencing the traumatic event. acute stress disorder , anxiety due to a medical condition , In some instances , a person shows symptoms of post generalized anxiety disorder, panic disorder, panic attack , a traumatic stress disorder within a month of experiencing the phobia , post - traumatic stress disorder, separation anxiety traumatic event. In some instances, a person shows symp disorder , social anxiety disorder , substance - induced anxiety toms of post - traumatic stress disorder within a year of disorder, or selective mutism . experiencing the traumatic event. In some instances, a US 2019 /0142851 A1 May 16 , 2019 35 person shows symptoms of post -traumatic stress disorder (0423 ] In some instances, an anxiety disorder comprises a after a year or more of experiencing the traumatic event. In medical diagnosis based on the criteria and classification some instances, post - traumatic stress disorder comprises a from the Diagnostic and Statistical Manual of Medical person re- experiencing the trauma event through intrusive Disorders, 5th Ed . In some instances , an anxiety disorder distressing recollections of the event, flashbacks , and /or comprises a medical diagnosis based on an independent nightmares . In some instances, a symptom ofpost -traumatic medical evaluation . In some instances , an anxiety disorder stress disorder comprises emotional numbness and avoid comprises a medical diagnosis based on a self- evaluation . ance of places , people , and activities that are reminders of [0424 ] In one embodiment, the methods and compositions the trauma. In some instances , a symptom of post - traumatic disclosed herein comprise administering an anxiolytic drug . stress disorder comprises increased arousal such as difficulty [0425 ] As used herein , the term “ anxiolytic drug” refers to sleeping and concentrating , feeling anxious , and being easily a compound or composition that reacts or influences activity irritated and angered . at a neurotransmitter receptor , e . g ., a serotonergic drug , an [ 0418 ] As used herein the term “ neurodegeneration ” refers adrenergic receptor, a dopamine receptor , a GABAergic to the progressive loss of structure or function of neurons , receptor, a glutaminergic receptor, a histaminergic receptor , including but not limited to the death of neurons . Many a cholinergic receptor, an opioid receptor, or a glycinergic neurodegenerative diseases , including amyotrophic lateral receptor, etc . In one embodiment, an anxiolytic drug binds sclerosis , Parkinson ' s disease , Alzheimer ' s disease, and on a neurotransmitter receptor. In one embodiment, an Huntington ' s disease occur as a result of neurodegenera - anxiolytic drug indirectly affects a neurotransmitter receptor, tive processes. Such diseases are incurable , resulting in e . g ., via interactions affecting the reactivity of other mol progressive degeneration and /or death of neuron cells . Some ecules at a neurotransmitter receptor. In one embodiment, an attempts have been made to treat such diseases and condi anxiolytic drug is an agonist. In one embodiment, an anxi tions using fungal and plant extracts . But those methods all olytic drug is an antagonist. In one embodiment, an anxi suffer from a common flaw in that the fungal and / or plants o lytic drug acts ( either directly or indirectly ) at more than extracts fail to provide consistent or reliable amounts of the one type of neurotransmitter receptor. therapeutic compounds on account of relying on the highly [0426 ] In one embodiment , an anxiolytic drug is chosen variable chemical compositions of particular naturally from alprazolam , an alpha blocker, an antihistamine , a occurring organisms. barbiturate , a beta blocker, bromazepam , a carbamate , [0419 ] As used herein , the term " separation anxiety dis chlordiazepoxide , clonazepam , clorazepate , diazepam , flu order ” refers to a condition wherein an individual is fearful razepam , lorazepam , an opioid , oxazepam , temazepam , or and / or anxious about separation from an attachment figure to triazolam . a degree that is developmentally inappropriate . In some [0427 ] As used herein , the term “ depressive disorder ” instances , a separation anxiety disorder comprises a fear or refers to a condition of low mood and aversion to activity anxiety about harm coming to an attachment figure . In some that can affect a person ' s thoughts , behavior, feelings , and instances, a separation anxiety disorder comprises a fear of sense of well- being lasting for a time period . In one embodi an event leading to the loss of or separation from an ment, a depressive disorder disrupts the physical and psy attachment figure and reluctance to go away from attach chological functions of a person . In one embodiment, a ment figures . In some instances , a separation anxiety disor depressive disorder causes a physiological symptom , e. g ., der comprises a nightmare and / or psychical symptom of weight loss , aches or pains, headaches , cramps , digestive distress . problems, etc . In one embodiment, a depressive disorder [0420 ] As used herein , the term “ social anxiety disorder ” causes a psychological symptom , e . g ., persistent sadness ; refers to a condition wherein an individual is fearful, anxious anxiety ; feelings of hopelessness and irritability ; feelings of about, or avoidant of social interactions and situations that guilt , worthlessness, or helplessness; loss of interest or involve the possibility of being scrutinized . These social pleasure in hobbies and activities ; difficulty concentrating , interactions and situations include meeting unfamiliar remembering , or making decisions, etc . people , situations in which the individualmay be observed [0428 ] In one embodiment, a depressive disorder is chosen eating or drinking , situations in which the individual per from atypical depression , bipolar disorder , catatonic depres forms in front of others, etc . In some instances, a social sion , depressive disorder due to a medical condition ,major anxiety disorder is caused by the fear of being negatively depressive disorder, postpartum depression , premenstrual evaluated by others , by being embarrassed , humiliated , dysphoric disorder, or seasonal affective disorder. rejected , and / or offending others . [0429 ] As used herein , the term “ atypical depression ” refers to a condition wherein an individual shows signs of [0421 ] As used herein , the term " substance -induced anxi mood reactivity ( i . e . , mood brightens in response to actual or ety disorder” refers to a condition wherein anxiety caused by potential positive events ) , significant weight gain , increase a substance intoxication and / or a withdrawal or to a medical in appetite , hypersomnia , heavy , leaden feelings in arms or treatment. In some instances , a withdrawal from a substance legs , and / or long -standing pattern of interpersonal rejection increases anxiety . sensitivity that results in significant social or occupational [0422 ] As used herein , the term “ selective mutism ” refers impairment. Exemplary symptoms of atypical depression to a condition characterized by an individual ' s consistent include , but are not limited to , daily sadness or depressed failure to speak in social situations in which there is an mood ; loss of enjoyment in things that were once pleasur expectation to speak , e . g . , school, a lecture , a meeting , etc . , able ; major changes in weight (gain or loss ) or appetite; even though the individual speaks in other situations. Failure insomnia or excessive sleep almost every day ; a state of to speak has significant consequences on achievement in physical restlessness or being rundown that is noticeable by academics , occupational settings , and/ or otherwise inter others ; daily fatigue or loss of energy ; feelings of hopeless feres with normal social communication . ness , worthlessness , or excessive guilt almost every day ; US 2019 /0142851 A1 May 16 , 2019 36 problems with concentration or making decisions almost person ' s personal, work , or school life, as well as sleeping, every day ; recurring thoughts of death or suicide , suicide eating habits, and general health . 2 - 7 % of adults with major plan , or suicide attempt. depressive disorder commit suicide , and up to 60 % of people [0430 ] As used herein , the term “ bipolar disorder” refers who commit suicide had a major depressive disorder or to a condition that causes an individual to experience another related mood disorder. Dysthymia is a subtype of unusual shifts in mood , energy , activity levels , and the major depressive disorder consisting of the same cognitive ability to carry out day - to - day tasks . Individuals with bipolar and physical problems as a major depressive disorder with disorder experience periods of unusually intense emotion , less severe but longer - lasting symptoms. Exemplary symp changes in sleep patterns and activity levels , and unusual toms of a major depressive disorder include , but are not behaviors . These distinct periods are called " mood epi limited to , feelings of sadness , tearfulness , emptiness or sodes. ” Mood episodes are drastically different from the hopelessness ; angry outbursts , irritability or frustration , moods and behaviors that are typical for the person . Exem even over small matters; loss of interest or pleasure in most plary symptoms of mania, excessive behavior, include , but or all normal activities , sleep disturbances , including insom are not limited to , abnormally upbeat, jumpy, or wired nia or sleeping too much ; tiredness and lack of energy ; behavior ; increased activity , energy, or agitation ; exagger reduced appetite , weight loss or gain ; anxiety , agitation or ated sense of well -being and self- confidence ; decreased need restlessness ; slowed thinking , speaking , or body move for sleep ; unusual talkativeness ; racing thoughts ; distract ments ; feelings of worthlessness or guilt , fixating on past ibility ; and poor decision -making — for example, going on failures or self -blame ; trouble thinking , concentrating , mak buying sprees , taking sexual risks, or making foolish invest ing decisions, and remembering things; frequent thoughts of ments . Exemplary symptoms of depressive episodes, low death , suicidal thoughts , suicide attempts , or suicide ; and mood , include , but are not limited by, depressed mood , such unexplained physical problems, such as back pain or head as feelings of sadness , emptiness , hopelessness , or tearful aches. ness; marked loss of interest or feeling no pleasure in all — or [0434 ] As used herein , the term “ postpartum depression ” almost all — activities ; significant weight loss , weight gain , refers to a condition as the result of childbirth and hormonal or decrease or increase in appetite ; insomnia or sleeping too changes, psychological adjustment to parenthood , and /or much ; restlessness or slowed behavior; fatigue or loss of fatigue . Postpartum depression is often associated with energy ; feelings of worthlessness or excessive or inappro women , butmen can also suffer from postpartum depression priate guilt ; decreased ability to think or concentrate , or as well . Exemplary symptoms of postpartum depression indecisiveness; and thinking about, planning or attempting include , but are not limited to , feelings of sadness, hopeless, suicide . emptiness , or overwhelmed , crying more often than usual or [0431 ] As used herein , the term " catatonic depression ” for no apparent reason ; worrying or feeling overly anxious ; refers to a condition causing an individual to remain speech feeling moody , irritable , or restless ; oversleeping , or being less and motionless for an extended period. Exemplary unable to sleep even when the baby is asleep ; having trouble symptoms of catatonic depression include , but are not lim concentrating , remembering details , and making decisions; ited to , feelings of sadness , which can occur daily , a loss of experiencing anger or rage ; losing interest in activities that interest in most activities, sudden weight gain or loss , a are usually enjoyable ; suffering from physical aches and change in appetite, trouble falling asleep , trouble getting out pains, including frequent headaches, stomach problems, and of bed , feelings of restlessness , irritability , feelings of worth muscle pain ; eating too little or too much ; withdrawing from lessness , feelings of guilt, fatigue , difficulty concentrating , or avoiding friends and family ; having trouble bonding or difficulty thinking , difficulty making decisions , thoughts of forming an emotional attachment with the baby ; persistently suicide or death , and /or a suicide attempt. doubting his or ability to care for the baby ; and thinking [0432 ] As used herein , the term “ depressive disorder due about harming themselves or the baby. to a medical condition ” refers to a condition wherein an [0435 ] As used herein , the term “ premenstrual dysphoric individual experiences depressive symptom caused by disorder ” refers to a condition wherein an individual another illness . Examples of medical conditions known to expresses mood lability, irritability , dysphoria , and anxiety cause a depressive disorder include , but are not limited to , symptoms that occur repeatedly during the premenstrual HIV / AIDS , diabetes , arthritis , strokes , brain disorders such phase of the cycle and remit around the onset of menses or as Parkinson ' s disease , Huntington ' s disease , multiple scle shortly thereafter. Exemplary symptoms of premenstrual rosis , and Alzheimer ' s disease , metabolic conditions ( e . g . dysphoric disorder include , but are not limited to , lability vitamin B12 deficiency ) , autoimmune conditions ( e . g . , lupus ( e . g ., mood swings ) , irritability or anger , depressed mood , and rheumatoid arthritis ), viral or other infections (hepatitis , anxiety , and tension , decreased interest in usual activities , mononucleosis , herpes ), back pain , and certain cancers ( e. g. , difficulty in concentration , lethargy and lack of energy, pancreatic ). change in appetite ( e . g ., overeating or specific food crav [0433 ] As used herein , the term “ major depressive disor ings ) , hypersomnia or insomnia , feeling overwhelmed or out der ” refers to a condition characterized by a time period of of control, physical symptoms ( e . g . , breast tenderness or low mood that is present across most situations . Major swelling, joint or muscle pain , a sensation of ' bloating ' and depressive disorder is often accompanied by low self - es weight gain ), self -deprecating thoughts , feelings of being teem , loss of interest in normally enjoyable activities , low keyed up or on edge , decreased interest in usual activities energy , and pain without a clear cause . In some instances , ( e . g ., work , school, friends, hobbies) , subjective difficulty in major depressive order is characterized by two weeks . In concentration , and easy fatigability . some instances, an individual experiences periods of depres [0436 ] As used herein , the term “ seasonal affective disor sion separated by years . In some instances , an individual der ” refers to a condition wherein an individual experiences experiences symptom of depression that are nearly always mood changes based on the time of the year. In some present. Major depressive disorder can negatively affect a instances , an individual experiences low mood , low energy, US 2019 /0142851 A1 May 16 , 2019 37

or other depressive symptoms during the fall and/ or winter a compulsion to perform tasks to relieve said feeling of season . In some instances, an individual experiences low anxiety . An obsession is a thought that recurs and persists mood , low energy , or other depressive symptoms during the despite the efforts of an individual to ignore or confront spring and/ or summer season . Exemplary symptoms of them . In some instances , an obsession is relatively vague seasonal affective disorder include , but are not limited to , involving a general sense of disarray or tension accompa feeling depressed most of the day or nearly every day ; losing nied by a belief that life cannot proceed as normal while the interest in activities once found enjoyable ; having low imbalance remains. In other instances , an obsession is more energy; having problems with sleeping ; experiencing intense and could be a preoccupation with the thought or changes in appetite or weight; feeling sluggish or agitated ; image of someone close to them dying or intrusions related having difficulty concentrating; feeling hopeless , worthless , to relationship rightness . Other obsessions concern the pos or guilty ; and having frequent thoughts of death or suicide . sibility that someone or something other than oneself — such [0437 ] In one embodiment, a depressive disorder com as God , the Devil, or disease will harm either the person , prises a medical diagnosis based on the criteria and classi the people or things that the person cares about . In some fication from Diagnostic and Statistical Manual of Medical instances, individuals perform compulsive rituals because Disorders , 5th Ed . In one embodiment, a depressive disorder they inexplicably feel they have to . In some instances , comprises a medical diagnosis based on an independent individuals perform compulsive rituals to mitigate the anxi medical evaluation . ety that stems from a particular obsession . The person feels [ 0438 ] In one embodiment, the methods and compositions that these actions will somehow either prevent a dreaded disclosed herein comprise administering an antidepressant. event from occurring or will push the event from their 04391 As used herein , the term “ antidepressant” refers to thoughts . a compound or compounds that reacts or influences activity [ 0447 ] In one embodiment, a compulsive disorder is cho at a neurotransmitter receptor, e . g ., a serotonergic drug , an sen from addiction , body dysmorphic disorder , excoriation adrenergic receptor , a dopamine receptor , a GABAergic disorder, hoarding disorder , obsessive - compulsive disorder, receptor , a glutaminergic receptor, a histaminergic receptor , and trichotillomania . a cholinergic receptor, an opioid receptor, or a glycinergic 10448 ] As used herein , the term " addiction ” refers to a receptor, etc . In one embodiment, an antidepressant binds on physical and /or psychological dependence on a substance , a neurotransmitter receptor. In one embodiment , an antide activity , and/ or any other habit . In one embodiment, an pressant indirectly affects a neurotransmitter receptor, e. g ., addiction is caused by the altered brain chemistry of an via interactions affecting the reactivity of other molecules at individual in response to a stimulus , e . g ., a substance a neurotransmitter receptor. In one embodiment, an antide releasing large amounts of serotonin , an activity releasing pressant is an agonist . In one embodiment , an antidepressant large amounts of adrenaline , etc . In one embodiment, an is an antagonist . In one embodiment, an antidepressant acts addiction is a dependence on a substance , e . g ., a drug , an ( either directly or indirectly ) at more than one type of alcohol, nicotine , a food , etc . In one embodiment, an addic neurotransmitter receptor. tion is a dependence on an activity , e . g . , gambling , eating , [0440 ] In one embodiment, an antidepressant is chosen shopping , etc . from bupropion , citalopram , duloxetine, escitalopram , flu 10449 ]. As used herein , the term “ body dysmorphic disor oxetine , fluvoxamine , milnacipran , mirtazapine , paroxetine , der ” refers to a condition characterized by the obsessive idea reboxetine , sertraline , and venlafaxine . that some aspect of an individual' s appearance is severely [ 0441 ) Disclosed herein is a method of treating headaches flawed and warrants exceptional measures to hide or fix it . and / or migraines, comprising identifying a person in need of Exemplary symptoms of body dysmorphic disorder treatment and administering a composition disclosed herein includes , but are not limited to , being extremely preoccupied to the person in need of treatment . with a perceived flaw in appearance that to others can ' t be [0442 ] Disclosed herein is a method of treating nicotine seen or appears minor ; a belief that a defect in appearance addiction , comprising identifying a person in need of treat makes an individual ugly or deformed ; a belief that others ment and administering a composition disclosed herein to take special notice of an individual ' s appearance in a nega the person in need of treatment. tive way or mock the individual; engaging in behaviors [0443 ] Disclosed herein is a method of treating drug aimed at fixing or hiding the perceived flaw that are difficult addiction , comprising identifying a person in need of treat to resist or control, such as frequently checking the mirror, ment and administering a composition disclosed herein to grooming, or skin picking ; attempting to hide perceived the person in need of treatment. flaws with styling, makeup , or clothes , constantly compar [0444 ] Disclosed herein is a method of treating alcohol ing one 's appearance with others ; always seeking reassur addiction , comprising identifying a person in need of treat ance about one ' s appearance from others ; having perfec ment and administering a composition disclosed herein to tionist tendencies ; seeking frequent cosmetic procedures the person in need of treatment . with little satisfaction ; avoiding social situations; and being [0445 ] The compositions disclosed herein are useful for so preoccupied with one ' s appearance that it causes major the treatment of compulsive disorders in humans, a variety distress or problems in a person ' s social life , work , school, of intractable psychiatric disorders , chronic depression , or other areas of functioning. post - traumatic stress disorder , and drug or alcohol depen [0450 ] As used herein , the term “ excoriation disorder ” dency. The compositions disclosed herein are also useful refers to a condition of having a repeated urge to pick at within the context of meditative , spiritual, and religious one ' s own skin . In some instances, an excoriation disorder practices within a variety of contexts . causes a person to often to pick their skin to the extent that [0446 ] As used herein , the term “ compulsive disorder ” damage is caused . refers to a condition wherein an individual has an obsession [0451 ] As used herein , the term “ hoarding disorder” refers causing a feeling of anxiety , fear, apprehension , etc ., and has to a condition of persistent difficulty in discarding or parting US 2019 /0142851 A1 May 16 , 2019 38 with possessions, regardless of their value. Exemplary [ 0454 ] In one embodiment , a compulsive disorder com symptoms of a hoarding disorder include, but are not limited prises a medical diagnosis based on the criteria and classi to , inability to throw away possessions ; severe anxiety when fication from Diagnostic and Statistical Manual of Medical attempting to discard items; great difficulty categorizing or Disorders , 5th Ed . In one embodiment, a compulsive disor organizing possessions ; indecision about what to keep or der comprises a medical diagnosis based on an independent where to put things ; distress , such as feeling overwhelmed medical evaluation . or embarrassed by possessions; suspicion of other people 10455 ) Disclosed herein are formulations comprising a touching items; obsessive thoughts and actions; fear of composition disclosed herein and at least one compound not running out of an item or of needing it in the future ; checking acting on serotonin receptors . the trash for accidentally discarded objects ; and functional [0456 ] Although the disclosed invention has been impairments, e . g . , loss of living space , social isolation , described with reference to various exemplary embodi family or marital discord , financial difficulties, health haz ments, it is to be understood that these embodiments are ards, etc . merely illustrative of the principles and applications of the [0452 ] As used herein , the term " obsessive - compulsive present invention . Those having skill in the art would disorder” refers to a condition in which an individual has recognize that various modifications to the exemplary uncontrollable, reoccurring thoughts and behaviors that he embodiments may be made, without departing from the or she feels the urge to repeat over and over . In some scope of the invention . instances, an obsessive - compulsive disorder manifests itself 104571 Where reference is made to a particular compound , as an individual needing to clean in order to reduce the fear it should be understood that this disclosure also contem that germs, dirt, or chemicals will contaminate the individual plates salts and derivatives of that compound as well as and the individual will spend many hours washing them degradation products , such as oxidized versions of explicitly selves or cleaning their surroundings . In some instances , an disclosed molecules. obsessive -compulsive disorder manifests itself as an indi [0458 ] Moreover, it should be understood that various vidual needing to dispel anxiety . An individual may utter a features and /or characteristics of differing embodiments name, phrase or repeat a behavior several times. The indi herein may be combined with one another . It is , therefore , to vidual knows these repetitions will not actually prevent be understood that numerous modifications may be made to injury, but fear of harm will occur if the repetitions are not the illustrative embodiments and that other arrangements performed . In some instances, an obsessive -compulsive dis may be devised without departing from the scope of the order manifests itself as an individual needing to reduce the invention . fear of harming oneself or by others by , e . g . , forgetting to f0459 ]. Furthermore , other embodiments of the invention lock the door or turning off appliances , developing checking will be apparent to those skilled in the art from consideration rituals , etc . In some instances , an obsessive - compulsive of the specification and practice of the invention disclosed disorder manifests itself as an individual needing to order herein . It is intended that the specification and examples be and arrange his or her surroundings to reduce discomfort , considered as exemplary only , with a scope and spirit being e . g ., putting objects in a certain order , arranging household indicated by the claims. items in a particular manner or in a symmetric fashion , etc . [0460 ] Finally , it is noted that, as used in this specification In some instances, an obsessive - compulsive disorder mani and the appended claims, the singular forms “ a , " " an , ” and fests itself as an individual needing to respond to intrusive “ the, ” include plural referents unless expressly and obsessive thoughts , e . g . , praying or saying phrases to reduce unequivocally limited to one referent and vice versa . As used anxiety or prevent a dreaded future event. In some instances, herein , the term “ include ” or “ comprising ” and its gram obsessive - compulsive disorder is caused by another medical matical variants are intended to be non - limiting , such that condition . In some instances, obsessive -compulsive disorder recitation of an item or items is not to the exclusion of other is caused by a substance . like items that can be substituted or added to the recited [0453 ] As used herein , the term “ trichotillomania ” refers item ( s ). to a condition of self- induced and recurrent loss of hair, e. g ., pulling one ' s own hair out. In some instances , trichotillo What is claimed is : mania comprises an individual pulling their hair out at one 1 . A composition , comprising: location . In some instances, trichotillomania comprises an a first purified psilocybin derivative ; and individual pulling their hair out at multiple locations. Exem plary symptoms of trichotillomania include, but are not a first purified cannabinoid . limited to , recurrent pulling out of one ' s hair resulting in 2 . The composition of claim 1 , wherein the first purified noticeable hair loss ; an increased sense of tension immedi psilocybin derivative is chosen from [ 3 -[ 2 -Dimethylamino ately before pulling out the hair or when resisting the ethyl ) - 1H - indol -4 -yl ] dihydrogen phosphate , 4 -hydroxy - N , behavior; pleasure , gratification , or relief when pulling out N -dimethyltryptamine , 3- ( 2 -methylaminoethyl ) - 1H - indol the hair ; the disturbance is not accounted for by another 4 -yl ] dihydrogen phosphate , 4 -hydroxy - N mental disorder and is not due to a general medical condition methyltryptamine, [ 3 - ( aminoethyl) - 1H - indol- 4 - yl ] ( i . e . , dermatological condition ) ; repeated attempts have been dihydrogen phosphate , 4 -hydroxytryptamine , [ 3 - ( 2 - trimeth made to decrease or stop hair pulling ; disturbances caused ylaminoethyl) - 1H - indol -4 -yl ] dihydrogen phosphate , or significant distress or impairment in social, occupational, or 4 -hydroxy - N , N , N -trimethyltryptamine . other important areas of functioning ; distress including 3. The composition of claim 2, wherein the first purified feelings of loss of control, embarrassment, shame ; and cannabinoid is chosen from THC , THCA , THCV, THCVA , impairment due to avoidance of work , school, or other CBC , CBCA , CBCV, CBCVA , CBD , CBDA , CBDV , public situations . CBDVA , CBG , CBGA , CBGV, or CBGVA . US 2019 /0142851 A1 May 16 , 2019 39

4 . The composition of claim 1 , wherein the first purified 14 . The composition of claim 11 , wherein the first psilo psilocybin derivative and the first purified cannabinoid are cybin derivative is a purified psilocybin derivative . present in the composition in a molar ratio of between 100 : 1 15 . The composition of claim 11 , wherein the first can to 1 : 100 . nabinoid is a purified cannabinoid . 5 . The composition of claim 4 , wherein the molar ratio is 16 . The composition of claim 14 , wherein the purified psilocybin derivative is chosen from [ 3 - 2 - Dimethylamino between 75 : 1 to 1 :75 . ethyl) - 1H - indol - 4 -yl ] dihydrogen phosphate , 4 -hydroxy - N , 6 . The composition of claim 5 , wherein the molar ratio is N - dimethyltryptamine , 3 - ( 2 -methylaminoethyl ) - 1H - indol between 50 : 1 to 1: 50 . 4 - yl] dihydrogen phosphate , 4 - hydroxy - N 7 . The composition of claim 6 , wherein the molar ratio is methyltryptamine , [ 3 -( aminoethyl) - 1H - indol - 4 - yl ] between 25 : 1 to 1: 25 . dihydrogen phosphate , 4 - hydroxytryptamine , [ 3 - ( 2 - trimeth 8 . The composition of claim 7 , wherein the molar ratio is ylaminoethyl) -1H - indol- 4 - yl ] dihydrogen phosphate , or between 10 : 1 to 1 : 10 . 4 -hydroxy - N , N , N -trimethyltryptamine . 9 . The composition of claim 8 , wherein the molar ratio is 17 . The composition of claim 15 , wherein the purified between 5 : 1 to 1 : 5 . cannabinoid is chosen from THC , THCA , THCV , THCVA , 10 . The composition of claim 1 , wherein the first psilo CBC , CBCA , CBCV, CBCVA , CBD CBDA , CBDV , cybin derivative and the first purified cannabinoid are pres CBDVA , CBG , CBGA , CBGV, or CBGVA . ent as a homogeneous mixture within the composition . 18 . The composition of claim 17 , wherein the purified 11 . A composition comprising a first psilocybin derivative cannabinoid is chosen from CBD , CBDA , CBC , or CBG . and a first cannabinoid . 19 . The composition of claim 11, comprising purified 12 . The composition of claim 11 , wherein the first psilo pyridine -3 -carboxylic acid . cybin derivative is chosen from [ 3 [ 2 -Dimethylaminoethyl ) 20 . The composition of claim 11, comprising purified a 1H - indol- 4 - yl] dihydrogen phosphate , 4 -hydroxy - N , N - dim compound chosen from purified erinacin A , purified erinacin ethyltryptamine, 3 - ( 2 -methylaminoethyl ) - 1H - indol- 4 - yl] B , purified erinacin C , purified erinacin D , purified erinacin dihydrogen phosphate , 4 -hydroxy - N -methyltryptamine , [ 3 E , purified erinacin F , purified erinacin G , purified erinacin (aminoethyl ) - 1H - indol- 4 - yl] dihydrogen phosphate , 4 -hy H , purified erinacin I , purified erinacin J , purified erinacin K , droxytryptamine , [ 3 - ( 2 -trimethylaminoethyl ) - 1H - indol- 4 purified erinacin I, purified erinacin P , purified erinacin Q , or yl] dihydrogen phosphate , or 4 -hydroxy - N , N , N purified erinacin R . trimethyltryptamine. 21. The composition of claim 11 , comprising purified 13 . The composition of claim 11 , wherein the first can hericinone A , purified hericinone B , purified hericinone C , nabinoid is chosen from THC , THCA , THCV , THCVA , purified hericinone D , purified hericinone E , purified heri CBC , CBCA , CBCV, CBCVA , CBD CBDA , CBDV, cinone F , purified hericinone G , and purified hericinone H . CBDVA , CBG , CBGA , CBGV, or CBGVA .