The following is a list of

psychedelic drug Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science o ...

s of various chemical classes, including both naturally occurring and synthetic compounds. Serotonergic psychedelics are usually considered the "classical" psychedelics, whereas the other classes are often seen as having only secondary psychedelic properties; nonetheless all of the compounds listed here are considered psychoactive and hallucinogenic in humans to some degree. Some of these compounds may be classified differently or under more than one category due to a unique structural classification, multiple mechanisms of action, or the fact that the precise

pharmacodynamic Pharmacodynamics (PD) is the study of the biochemical and physiologic effects of drugs (especially pharmaceutical drugs). The effects can include those manifested within animals (including humans), microorganisms, or combinations of organisms (for ...

actions of the compound are not yet completely understood. Because of the vast amount of possible substitutions and chemical analogs of most psychedelic compounds, the total diversity of chemical compounds which produce psychedelic effects in humans is not fully reflected within this list, leaving room for many that have not yet been sufficiently investigated and others that have not yet been discovered. Naturally occurring compounds are marked with a †.

Serotonergic psychedelics ( serotonin 5-HT_2A receptor agonists)

Indoles Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environment ...

Tryptamine Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...

s (more specifically alkylated tryptamines]) ***

Psilocin Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated cou ...

†, also known as '4-HO-DMT'; another active constituent of the ''

Psilocybe ''Psilocybe'' ( ) is a genus of gilled mushrooms, growing worldwide, in the family Hymenogastraceae. Most or nearly all species contain the psychedelic compounds psilocybin and psilocin. Taxonomy Taxonomic history A 2002 study of the m ...

'' genus of mushrooms; also a metabolite of psilocybin and psilacetin ***

Psilocybin Psilocybin ( , ) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of the genus ''Psilocybe'', such as '' P. azurescens'', '' P. semilanceata'', and '' P.&nbs ...

†, also known as '4-PO-DMT'; the primary active constituent of the ''

'' genus of mushrooms; its effects are partially attributed to psilocin, to which it is a

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the dru ...

via

dephosphorylation In biochemistry, dephosphorylation is the removal of a phosphate (PO43−) group from an organic compound by hydrolysis. It is a reversible post-translational modification. Dephosphorylation and its counterpart, phosphorylation, activate and de ...

***

Bufotenin Bufotenin (5-HO-DMT, bufotenine) is a tryptamine derivative - more specifically, a DMT derivative - related to the neurotransmitter serotonin. It is an alkaloid found in some species of toads (especially the skin), mushrooms and plants. ...

†, also known as '5-HO-DMT' and dimethylserotonin; another constituent of the skin and venom of

psychoactive toads The Colorado River toad (''Incilius alvarius''), formerly known as the Sonoran Desert toad, is found in northern Mexico and the southwestern United States. It exudes toxins from glands within its skin that have psychoactive properties. Descript ...

, its psychedelic activity is disputed; also a metabolite of 5-MeO-DMT *** Baeocystin†, also known as '4-PO-NMT'; another active constituent of the ''

'' genus of mushrooms; its psychedelic activity is disputed *** Aeruginascin†, also known as '4-PO-N-TMT', an active constituent of the mushroom '' Inocybe aeruginascens'' ***

5-MeO-DMT 5-MeO-DMT (5-methoxy-''N'',''N''-dimethyltryptamine) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado R ...

†, the primary active constituent of the skin and venom of

, a prodrug to bufotenin via

demethylation Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen at ...

*** ''N,N''-Dimethyltryptamine†, also known as 'DMT'; the primary active constituent of the Amerindian brew

ayahuasca AyahuascaPronounced as in the UK and in the US. Also occasionally known in English as ''ayaguasca'' ( Spanish-derived), ''aioasca'' (Brazilian Portuguese-derived), or as ''yagé'', pronounced or . Etymologically, all forms but ''yagé'' desce ...

; endogenously present in various plants and animals, including humans, possibly a

trace amine Trace amines are an endogenous group of trace amine-associated receptor 1 (TAAR1) agonists – and hence, monoaminergic neuromodulators – that are structurally and metabolically related to classical monoamine neurotransmitters. Compared to th ...

neurotransmitter *** 5-Bromo-DMT†, was found in the marine

invertebrate Invertebrates are a paraphyletic group of animals that neither possess nor develop a vertebral column (commonly known as a ''backbone'' or ''spine''), derived from the notochord. This is a grouping including all animals apart from the chorda ...

s '' Smenospongia aurea'' and '' Smenospongia echina'', as well as in '' Verongula rigida'' *** ''N''-Methyl-''N''-ethyltryptamine, also known as 'MET' *** ''N''-Methyl-''N''-isopropyltryptamine, also known as 'MiPT' *** N- Methyl-N-propyltryptamine, also known as 'MPT' *** ''N,N''-Diethyltryptamine, also known as 'DET' *** ''N''-Ethyl-''N''-isopropyltryptamine, also known as 'EiPT' *** ''N''-Methyl-''N''-butyltryptamine, also known as 'MBT' *** ''N''-Propyl-''N''-isopropyltryptamine, also known as 'PiPT' *** ''N,N''-Dipropyltryptamine, also known as 'DPT' *** ''N,N''-Diisopropyltryptamine, also known as 'DiPT' *** ''N,N''-Diallyltryptamine, also known as 'DALT' *** ''N,N''-Dibutyltryptamine, also known as 'DBT' *** ''N''-Ethyltryptamine, also known as 'NET' *** ''N''-Methyltryptamine†, also known as 'NMT'; its psychedelic activity is disputed *** Trimethyltryptamine, also known as 'TMT' ( 2,N,N-TMT, 5,N,N-TMT, and 7,N,N-TMT) *** α-Methyltryptamine, also known as 'αMT' and 'AMT'; also has entactogenic properties *** α-Ethyltryptamine, also known as 'αET' and 'AET'; also has entactogenic properties *** α,''N''-DMT ***

α,N,N-Trimethyltryptamine α,''N'',''N''-Trimethyltryptamine (α,''N'',''N''-TMT, α-TMT, ATMT) is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic hallucinogen. It is similar in structure to the other psychedelics of the tryptamine class ...

, also known as 'α-TMT' ***

Ethocybin Ethocybin (CEY-19; 4-phosphoryloxy-DET; 4-PO-DET) is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Effects of ethocybin are comparable to those of a shorter LSD or psilocybi ...

, also known as '4-PO-DET', 'CEY-19', and 'CEY-39' *** 4-HO-MET, also known as 'Metocin', 'Methylcybin', and 'Colour' ***

4-HO-DET 4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT. Analogs Th ...

, also known as 'Ethocin' and 'CZ-74' *** 4-HO-MPT, also known as 'Meprocin' *** 4-HO-MiPT, also known as 'Miprocin' *** 4-HO-MALT *** 4-HO-DPT, also known as 'Deprocin' *** 4-HO-DiPT, also known as 'Iprocin' *** 4-HO-DALT, also known as 'Daltocin' ***

4-HO-DBT 4-Hydroxy-''N,N''-dibutyltryptamine (4-HO-DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. 4-HO-DBT was first made by the chemist Alexande ...

*** 4-HO-DSBT *** 4-HO-αMT ***

4-HO-MPMI 4-HO-MPMI (also known as 4-Hydroxy-''N''-methyl-(α,''N''-trimethylene)-tryptamine or lucigenol) is a tryptamine derivative that is a psychedelic drug. It was developed by the team led by David Nichols from Purdue University in the late 1990s. T ...

, also known as 'Lucigenol' *** 4-HO-TMT *** 4-HO-1,N,N-TMT, also known as '1-Me-4-HO-DMT' and '1-methylpsilocin' *** 4-HO-5-MeO-DMT, also known as 'Psilomethoxin' ***

4-AcO-DMT ''O''-Acetylpsilocin (also known as psilacetin, 4-acetoxy-DMT, 4-AcO-DMT, or synthetic shrooms) is a semi-synthetic psychoactive drug that has been suggested by David Nichols to be a potentially useful alternative to psilocybin for pharmacolog ...

, also known as 'psiloacetin'; its effects are partially attributed to psilocin, to which it is a prodrug via

deacetylation : In organic chemistry, acetylation is an organic esterification reaction with acetic acid. It introduces an acetyl group into a chemical compound. Such compounds are termed ''acetate esters'' or simply '' acetates''. Deacetylation is the oppo ...

*** 4-AcO-MET, also known as 'Metacetin' ***

4-AcO-MiPT 4-AcO-MiPT (4-acetoxy-''N''-methyl-''N''-isopropyltryptamine or mipracetin) is a psychedelic tryptamine. It is closely related to ''O''-acetylpsilocin and MiPT. There is very little information on the human pharmacology or toxicity of 4-AcO-MiP ...

*** 4-AcO-MALT ***

4-AcO-DET 4-Acetoxy-DET (4-Acetoxy-''N'',''N''-diethyltryptamine), also known as ethacetin, ethylacybin or 4-AcO-DET, is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

, also known as 'Ethacetin' *** 4-AcO-EiPT, also known as 'Ethipracetin' *** 4-AcO-DPT, also known as 'Depracetin' *** 4-AcO-DiPT, also known as 'Ipracetin' *** 4-AcO-DALT, also known as 'Daltacetin' ***

4-MeO-DMT 4-MeO-DMT (4-methoxy-''N'',''N''-dimethyltryptamine) is a tryptamine derivative which has some central activity in animal tests similar to that of related psychedelic tryptamine drugs, although with significantly lower potency than either 5-MeO-D ...

***

4-MeO-MiPT 4-MeO-MiPT, or 4-methoxy-''N''-methyl-''N''-isopropyltryptamine, is a lesser-known psychedelic drug. It is the 4-methoxy analog of MiPT. 4-MeO-MiPT was first synthesized by Alexander Shulgin and is mentioned in his book ''TiHKAL'' (''Tryptamine ...

***

5-MeO-NMT 5-MeO-NMT (5-methoxy-''N''-methyltryptamine) is an organic chemical compound, being the 5-methoxy analog of ''N''-methyltryptamine (NMT). It was first isolated from ''Phalaris arundinacea'' (reed canary grass). It has also been synthesized by Al ...

† *** 5-MeO-MET *** 5-MeO-MPT ***

5-MeO-MiPT 5-MeO-MiPT is a psychedelic and hallucinogenic drug, used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because ...

, also known as 'Moxy'; also has entactogenic properties *** 5-MeO-MALT *** 5-MeO-DET ***

5-MeO-EiPT 5-MeO EiPT is a psychedelic of the tryptamine class that has been sold online as a designer drug. Legality 5-MeO-EiPT is illegal in Japan. 5-MeO-EiPT is illegal in Italy. Sweden's public health agency suggested classifying 5-MeO-EiPT as a hazardo ...

*** 5-MeO-EPT *** 5-MeO-PiPT *** 5-MeO-DPT ***

5-MeO-DiPT 5-Methoxy-''N'',''N''-diisopropyltryptamine (5-MeO-DiPT, sometimes called Foxy Methoxy or simply Foxy) is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT). Pharmacology The mechanism that produces the purport ...

, also known as 'Foxy Methoxy' *** 5-MeO-DALT *** 5-MeO-αMT, also has entactogenic properties *** 5-MeO-αET, also has entactogenic properties ***

5-MeO-MPMI 5-MeO-MPMI (also known as 5-Methoxy-''N''-methyl-(α,''N''-trimethylene)tryptamine) is a tryptamine derivative that is a psychedelic drug. It was first developed by the team led by JE Macor in 1992, and subsequently investigated by the team led b ...

*** 5-MeO-2,N,N-TMT , also known as 'Indomethacin' and 'Indapex' *** 5-MeO-7,N,N-TMT *** 5-MeO-a,N-DMT, also known as 'α,N,O-TMS' *** 4-F-5-MeO-DMT *** 5-MeS-DMT *** 5-Me-MiPT, its psychedelic activity is disputed ***

5-HO-DiPT 5-HO-DiPT (5-hydroxy-''N,N''-di-''iso''-propyltryptamine) is a tryptamine derivative which acts as a serotonin receptor agonist. It is primarily known as a metabolite of the better known psychoactive drug 5-MeO-DiPT, but 5-HO-DiPT has also rarely ...

*** 2-α-DMT *** 2-Me-DET *** 4-Me-αMT *** 4-Me-αET, also has entactogenic properties *** 7-Me-αET, also has entactogenic properties *** 4,5-DHP-AMT, also known as 'AL-37350A' *** 4,5-DHP-DMT *** 4,5-MDO-DMT *** 4,5-MDO-DiPT *** 5,6-MDO-DiPT *** 5,6-MDO-MiPT *** 5-Fluoro-αMT, also has entactogenic properties *** 6-Fluoro-αMT *** 6-Fluoro-DMT *** ''N,N''-Tetramethylenetryptamine, also known as 'Pyr-T' ***

4-HO-pyr-T 4-HO-pyr-T (4-hydroxy-''N'',''N''-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 4-hydroxyl analog of pyr-T. 4-HO-pyr-T was first synthesized by Alexander Shulgin. In his book ''TiHKAL ''TIHKAL: The Continuation' ...

***

5-MeO-pyr-T 5-MeO-pyr-T (5-methoxy-''N'',''N''-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemi ...

*** RU-28306, also known as '4,a-Methylene-N,N-DMT' ***

O-4310 O-4310 (1-isopropyl-6-fluoro-psilocin) is a tryptamine derivative developed by Organix Inc which acts as a serotonin receptor agonist. It is claimed to have an EC50 of 5nM at 5-HT2A with 89% efficacy vs 5-HT, and 100x selectivity over 5-HT2C, ...

, also known as '6-Fluoro-1-Isopropyl-4-HO-DMT' ***

CP-132,484 CP-132,484 is a tryptamine derivative which acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors. It has reasonable selectivity for 5-HT2A and 5-HT2C subtypes over 5-HT2B, but is only slightly selective for 5-HT2A ...

, also known as '4,5-DHP-1-Methyltryptamine' **

Benzofuran Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the "parent" of many related compounds with more complex structures. For example, psoralen is ...

derivatives (technically not tryptamines) ***

Dimemebfe Dimemebfe (5-MeO-BFE) is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indol ...

, also known as '5-MeO-BFE' ***

5-MeO-DiBF 5-MeO-DiBF is a psychedelic that has been sold online as a designer drug and was first definitively identified in December 2015 by a forensic laboratory in Slovenia. It is thought to act as an agonist for the 5-HT1A and 5-HT2 family of serotoni ...

** Ibogoids (can be classified as complex tryptamines) ***

Ibogaine Ibogaine is a naturally occurring psychoactive substance found in plants in the family Apocynaceae such as '' Tabernanthe iboga'', '' Voacanga africana'', and '' Tabernaemontana undulata''. It is a psychedelic with dissociative properties. Pre ...

†, the primary active constituent of

iboga ''Tabernanthe iboga'' (iboga) is an evergreen rainforest shrub native to Central Africa. A member of the Apocynaceae family indigenous to Gabon, the Democratic Republic of Congo, and the Republic of Congo, it is cultivated across Central Africa ...

rootbark; also has

dissociative Dissociatives, colloquially dissos, are a subclass of hallucinogens which distort perception of sight and sound and produce feelings of detachment – dissociation – from the environment and/or self. Although many kinds of drugs are capable of ...

properties ***

Voacangine Voacangine (12-methoxyibogamine-18-carboxylic acid methyl ester) is an alkaloid found predominantly in the root bark of the '' Voacanga africana'' tree, as well as in other plants such as ''Tabernanthe iboga'', '' Tabernaemontana africana'', ''Tra ...

†, another active constituent of

rootbark **

Ergolines Ergoline is a chemical compound whose structural skeleton is contained in a variety of alkaloids, referred to as ergoline derivatives or ergoline alkaloids. Ergoline alkaloids, one being ergine, were initially characterized in ergot. Some of the ...

(more specifically

lysergamides Amides of lysergic acid are collectively known as lysergamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine Receptor (biochemistry), receptors. See also * Ergoline * Brom ...

, which can be classified as complex tryptamines; also contain a phenethylamine backbone) ***

Lysergic acid diethylamide Lysergic acid diethylamide (LSD), also known colloquially as acid, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages LSD manifests primarily mental, vi ...

, also known as 'LSD' and 'acid' *** Lysergic acid amide†, also known as 'LSA' and 'ergine'; the primary active constituent of

morning glory Morning glory (also written as morning-glory) is the common name for over 1,000 species of flowering plants in the family Convolvulaceae, whose current taxonomy and systematics are in flux. Morning glory species belong to many genera, some of ...

and

Hawaiian baby woodrose ''Argyreia nervosa'' is a perennial climbing vine native to the Indian subcontinent and introduced to numerous areas worldwide, including Hawaii, Africa, and the Caribbean. Though it can be invasive, it is often prized for its aesthetic and med ...

seeds; an active constituent of some species of fungi *** Lysergic acid 2-butyl amide, also known as 'LSB' ***

Lysergic acid 3-pentyl amide Lysergic acid 3-pentyl amide (3-Pentyllysergamide, LSP) is an analogue of LSD originally researched by David E. Nichols and colleagues at Purdue University. It has similar binding affinity to LSD itself as both a 5-HT1A and 5-HT2A agonist, and ...

, also known as 'LSP' *** Lysergic acid methyl ester, also known as 'LSME' *** Lysergic acid 2,4-dimethylazetidide, also known as 'LSZ' and 'LA-SS-Az' *** Lysergic acid piperidine, also known as 'LSD-Pip'; its psychedelic activity is disputed *** ''N,N''-Dimethyl-lysergamide, also known as 'DAM-57' ***

Methylisopropyllysergamide Methylisopropyllysergamide (lysergic acid methylisopropyl amide, MIPLA) is an analogue of LSD that was originally discovered by Albert Hofmann at Sandoz during the original structure-activity research into LSD. It has subsequently been investigat ...

, also known as 'MIPLA' *** ''N,N''-Diallyllysergamide, also known as 'DAL' *** ''N''-Pyrrolidyllysergamide, also known as 'LPD-824' *** ''N''-Morpholinyllysergamide, also known as 'LSM-775' *** 1-methyl-lysergic acid butanolamide, also known as 'Methysergide'; the active constituent of Sansert and Deseril; a prodrug which has to be metabolized to methylergometrine to become psychoactive *** Lysergic acid β-propanolamide†, also known as 'Ergonovine' and 'Ergometrine'; another active constituent of

seeds, and an active constituent of

ergot Ergot ( ) or ergot fungi refers to a group of fungi of the genus ''Claviceps''. The most prominent member of this group is '' Claviceps purpurea'' ("rye ergot fungus"). This fungus grows on rye and related plants, and produces alkaloids that c ...

fungi *** Lysergic acid 1-butanolamide†, also known as 'Methylergonovine', 'Methergine', and 'Methylergometrine'; another active constituent of

seeds and of

fungi *

Phenethylamine Phenethylamine (PEA) is an organic compound, natural monoamine alkaloid, and trace amine, which acts as a central nervous system stimulant in humans. In the brain, phenethylamine regulates monoamine neurotransmission by binding to trace am ...

s (more specifically

alkoxy In chemistry, the alkoxy group is an alkyl group which is singularly bonded to oxygen; thus . The range of alkoxy groups is vast, the simplest being methoxy (). An ethoxy group () is found in the organic compound ethyl phenyl ether (, also ...

lated phenethylamines) ** Substituted phenethylamines ***

Mescaline Mescaline or mescalin (3,4,5-trimethoxyphenethylamine) is a naturally occurring psychedelic protoalkaloid of the substituted phenethylamine class, known for its hallucinogenic effects comparable to those of LSD and psilocybin. Biological ...

†, the primary active constituent of certain cacti, such as

peyote The peyote (; ''Lophophora williamsii'' ) is a small, spineless cactus which contains Psychoactive cactus, psychoactive alkaloids, particularly mescaline. ''Peyote'' is a Spanish word derived from the Nahuatl (), meaning "caterpillar Pupa#Cocoo ...

and San Pedro ***

Lophophine Lophophine (MMDPEA or 3-methoxy-4,5-methylenedioxyphenethylamine) is a putative psychedelic and entactogen drug of the methylenedioxyphenethylamine class. It is the α- demethylated homologue of MMDA, and is also closely related to mescaline ...

†, also known as 'MMDPEA'; another active constituent of certain cacti, such as

and San Pedro; also has entactogenic properties *** Isomescaline ***

Cyclopropylmescaline Cyclopropylmescaline (CPM or 4-cyclopropylmethoxy-3,5-dimethoxyphenethylamine) is a lesser-known psychedelic drug. CPM was first synthesized by Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an Ame ...

*** Thioisomescaline (2-TIM, 3-TIM, and 4-TIM) *** 4-Desoxymescaline *** Jimscaline ***

Escaline Escaline (3,5-methoxy-4-ethoxyphenethylamine) is a psychedelic drug and entheogen of the phenethylamine class of compounds. Escaline was first synthesized and reported in the scientific literature by Benington, et al., in 1954, but was later re-ex ...

*** Metaescaline *** Thiometaescaline (3-TME, 4-TME, and 5-TME) *** Trisescaline *** Thiotrisescaline (3-T-TRIS and 4-T-TRIS) *** Symbescaline *** Asymbescaline *** Thiosymbescaline (3-TSB and 4-TSB) *** Phenescaline *** Allylescaline, also known as 'AL' *** Methallylescaline *** Proscaline *** Isoproscaline *** Metaproscaline *** Thioproscaline *** Buscaline *** Thiobuscaline *** α-ethylmescaline, also known as 'AEM' ***

Ariadne Ariadne (; grc-gre, Ἀριάδνη; la, Ariadne) was a Cretan princess in Greek mythology. She was mostly associated with mazes and labyrinths because of her involvement in the myths of the Minotaur and Theseus. She is best known for having ...

, also known as 'α-Et-DOM', '4C-D', and 'Dimoxamine' *** Macromerine *** MEPEA *** TOM (2-TOM and 5-TOM) *** Bis-TOM ***

TOMSO TOMSO (2-methoxy-4-methyl-5-methylsulfinylamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. TOMSO was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', the dosage range is listed as 100–150 mg, a ...

, also known as '2-methoxy-4-methyl-5-methylsulfinylamphetamine' *** TOET (2-TOET and 5-TOET) *** BOH *** BOM, also known as 'β-Methoxy-mescaline' *** β-D *** 4-D *** DME *** F-2 *** F-22 ***

FLEA Flea, the common name for the order Siphonaptera, includes 2,500 species of small flightless insects that live as external parasites of mammals and birds. Fleas live by ingesting the blood of their hosts. Adult fleas grow to about long, ...

, also known as 'MDHMA' *** MDPH *** MDMP *** Propynyl ***

2C family 2C (2C-''x'') is a general name for the family of psychedelic drug, psychedelic phenethylamines containing Methoxy, methoxy groups on the 2 and 5 carbon, positions of a benzene ring. Most of these compounds also carry lipophilic substituents at the ...

(2,5-dimethoxy, 4-substituted phenethylamines) ****

βk-2C-B βk-2C-B (Bk-2C-B; 2-Amino-1-(4-bromo-2,5-dimethoxyphenyl)ethan1-one) is a novel psychedelic substance. It is the beta (β) ketone structural analogue of 2C-B, a psychedelic drug of the 2C family. It is used as a recreational drug, usually take ...

****

2C-B 2C-B (4-Bromo-2,5-dimethoxyphenethylamine) is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin in 1974. In Shulgin's book '' PiHKAL'', the dosage range is listed as 12–24 mg. As a recreational drug, 2C-B is so ...

**** 2CB-2EtO **** 2CB-5EtO **** 2CB-diEtO ****

2C-B-FLY 2C-B-FLY is a psychedelic phenethylamine and designer drug of the 2C family. It was first synthesized in 1996 by Aaron P. Monte. Chemistry 2C-B-FLY is 8-bromo-2,3,6,7-benzo-dihydro-difuran-ethylamine. The full name of the chemical is 2-(8-bromo ...

****

2C-B-BUTTERFLY 2C-B-BUTTERFLY (2C-B-MOTH-BIKHIR, 2C-B-BFLY) is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, which was discovered in 1999 by Michael S. Whiteside and Aaron Monte. It is a ring-expanded homologue of the bette ...

****

2C-C 2C-C is a psychedelic drug of the 2C family. It was first synthesized by Alexander Shulgin, sometimes used as an entheogen. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', Shulgin lists the dosage range as 20–40 mg. 2C-C ...

****

2C-D 2C-D (2,5-dimethoxy-4-methylphenethylamine or 2C-M) is a psychedelic drug of the 2C family that is sometimes used as an entheogen. It was first synthesized in 1970 by a team from the Texas Research Institute of Mental Sciences, and its activity wa ...

**** 2CD-2EtO **** 2CD-diEtO **** 2CD-5EtO ****

2C-E 2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and documented in his book '' PiHKAL''. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactio ...

**** 2C-EF **** 2C-F **** 2C-G (2C-G-1, 2C-G-2, 2C-G-3, 2C-G-4, 2C-G-5, 2C-G-6, and 2C-G-N) ****

2C-H 2C-H (2,5-dimethoxyphenethylamine) is a lesser-known substituted phenethylamine of the 2C family. History 2C-H was first synthesized in 1932 by Johannes S. Buck. Use 2C-H is used as a precursor in the synthesis of other substituted phenethyla ...

****

2C-I 2C-I is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and described in his 1991 book '' PiHKAL'' (''Phenethylamines I Have Known and Loved''). The drug has been used recreationally as psychedelic and ...

**** 2CI-2EtO ****

2C-iP 2C-iP (also known as Jelena) is a relatively potent and long acting psychedelic phenethylamine and compound from the 2C family that was first synthesized by Dmitri Ger and has been sold online as a designer drug. It is a structural analog of 2C ...

****

2C-N 2C-N (2,5-dimethoxy-4-nitrophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin. Chemistry The full name of the chemical is 2-(2,5-dimethoxy-4-nitrophenyl)ethanamine. Salts of 2C-N have ...

**** 2C-O **** 2C-O-4 ****

2C-P 2C-P is a relatively potent and long acting psychedelic phenethylamine of the 2C family. Chemistry 2C-P is 2,5-dimethoxy-4-''n''-propylphenethylamine. The full name of the chemical is 2-(2,5-dimethoxy-4-propylphenyl)ethanamine. The hydrochlorid ...

**** 2C-SE ****

2C-T 2C-T (or 4-methylthio-2,5-DMPEA) is a psychedelic and hallucinogenic drug of the 2C family. It is used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs mescaline and 2C-T-2. It was first synthesize ...

**** 2CT-5EtO ****

2C-T-2 2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug h ...

**** 2CT-2-2EtO **** 2CT-2-5EtO **** 2CT-2-diEtO ****

2C-T-4 2C-T-4 (2,5-dimethoxy-4-isopropylthiophenethylamine) is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and is used as entheogenic recreational drug. Chemistry 2C-T-4 is the 2-carbon homolog of a ...

(2C-T-4 and Ψ-2C-T-4) **** 2CT-4-2EtO ****

2C-T-7 2C-T-7 is a psychedelic phenethylamine of the 2C family. In his book '' PiHKAL: A Chemical Love Story'', Alexander Shulgin lists the dosage range as 10 to 30 mg. 2C-T-7 is generally taken orally, and produces psychedelic and entactogenic eff ...

**** 2CT-7-2EtO **** 2C-T-8 **** 2C-T-9 **** 2C-T-13 ****

2C-T-15 2C-T-15 or 2,5-dimethoxy-4-(β-cyclopropylthio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book '' PiHKAL (Phenethylamines i Have Known And Loved) ...

****

2C-T-16 2C-T-16 is a lesser-known psychedelic drug. It was originally named by Alexander Shulgin as described in his book PiHKAL (Phenethylamines i Have Known And Loved), however while Shulgin began synthesis of this compound he only got as far as the ...

****

2C-T-17 2C-T-17 or 2,5-dimethoxy-4-(β-secbutyl thio)phenethylamine is a psychedelic phenethylamine of the 2C family. It was presumably first synthesized by Alexander Shulgin and reported in his book '' PiHKAL (Phenethylamines i Have Known And Loved)''. ...

**** 2C-T-19, **** 2C-T-21 **** 2C-TFM **** 2C-YN **** BOB, also known as 'β-Methoxy-2C-B' **** BOD, also known as 'β-Methoxy-2C-D' **** BOHD, also known as 'β-Hydroxy-2C-D' **** HOT-2 **** HOT-7 **** HOT-17 **** Indane derivatives (technically not phenethylamines) *****

2CB-Ind 2CB-Ind is a conformationally-restricted derivative of the phenethylamine hallucinogen 2C-B, discovered in 1974 by Alexander Shulgin. It acts as a moderately potent and selective agonist for the 5-HT2A and 5-HT2C receptors, but unlike the co ...

**** Benzocyclobutene derivatives (technically not phenethylamines) ***** 2C-BCB, also known as 'TCB-2' **** NBOMe derivatives *****

NBOMe-mescaline NBOMe-mescaline or mescaline-NBOMe is a synthetic substituted phenethylamine. It is a partial agonist of serotonin receptors with a 5-HT2A pKi originally reported as 7.3 (i.e. Ki of approximately 50nM), though more modern techniques assayed it as ...

***** 2C-H-NBOMe, also known as '25H-NBOMe' ***** 2C-C-NBOMe, also known as '25C-NBOMe' *****

2CBCB-NBOMe 2CBCB-NBOMe (NBOMe-TCB-2) is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2007 at Purdue University as part of the ongoing research program of the team led by David Nichols focusing on ...

, also known as 'NBOMe-TCB-2' *****

2CBFly-NBOMe 2CBFly-NBOMe (NBOMe-2C-B-FLY, Cimbi-31) is a compound indirectly derived from the phenethylamine hallucinogen 2C-B, and related to benzodifurans like 2C-B-FLY and ''N''-benzylphenethylamines like 25I-NBOMe. It was discovered in 2002, and further ...

, also known as 'Cimbi-31' ***** 2C-B-NBOMe, also known as '25B-NBOMe', 'M25B-NBOMe', 'BOM 2-CB', 'Cimbi-36', 'Nova', or 'New Nexus' ***** 2C-I-NBOMe, also known as '25I-NBOMe', 'Cimbi-5', "Solaris", or "N-Bomb" ***** 2C-TFM-NBOMe, also known as '25TFM-NBOMe' ***** 2C-D-NBOMe, also known as '25D-NBOMe' ***** 2C-G-NBOMe, also known as '25G-NBOMe' ***** 2C-E-NBOMe, also known as '25E-NBOMe' ***** 2C-P-NBOMe, also known as '25P-NBOMe' ***** 2C-iP-NBOMe, also known as '25iP-NBOMe' ***** 2C-CN-NBOMe, also known as '25CN-NBOMe' ***** 2C-N-NBOMe, also known as '25N-NBOMe' ***** 2C-T-NBOMe, also known as '25T2-NBOMe' ***** 2C-T-4-NBOMe, also known as '25T4-NBOMe' ***** 2C-T-7-NBOMe, also known as '25T7-NBOMe' *****

DMBMPP DMBMPP, or 2-(2,5-dimethoxy-4-bromobenzyl)-6-(2-methoxyphenyl)piperidine, is a 2-benzylpiperidine analog of the hallucinogenic ''N''-benzylphenethylamine 25B-NBOMe and was discovered in 2011 by Jose Juncosa in the group of David E. Nichols at ...

, 2-Benzylpiperidine analogue of 25B-NBOMe **** NBOH derivatives ***** 2C-C-NBOH, also known as '25C-NBOH' and 'NBOH-2CC' ***** 2C-B-NBOH, also known as '25B-NBOH' ***** 2C-I-NBOH, also known as '25I-NBOH' ***** 2C-CN-NBOH, also known as '25CN-NBOH' and 'NBOH-2C-CN' **** NBMD derivatives ***** 2C-I-NBMD, also known as '25I-NBMD' **** NBF derivatives ***** 2C-C-NBF, also known as '25C-NBF' ***** 2C-B-NBF, also known as '25B-NBF' ***** 2C-I-NBF, also known as '25I-NBF' ** Substituted

amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...

s (''a''lpha-''m''ethyl-''ph''en''et''hyl''amines'') *** 3C family (3,5-dimethoxy, 4-substituted amphetamines) ****

3C-E 3C-E is a psychedelic of the amphetamine class. It was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', Shulgin lists the dosage range as 30 to 60 mg, consumed orally. The duration of action was stated to be 8–12 hours. T ...

****

3C-P 3C-P (α-Methyl-4-propoxy-3,5-dimethoxyphenethylamine) is a psychedelic phenethylamine. It has structural and pharmacodynamic properties similar to the drugs mescaline, proscaline, and amphetamine. Little information exists on the human pharmac ...

**** 3C-DFE ****

3C-BZ 3C-BZ (4-benzyloxy-3,5-dimethoxyamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. 3C-BZ was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', the dosage range is listed as 25–200 mg and the durat ...

*** DOx family (2,5-dimethoxy, 4-substituted amphetamines) **** DOAM **** DOB **** Meta-DOB **** Methyl-DOB ****

DOBU 2,5-Dimethoxy-4-butylamphetamine (DOBU) is a lesser-known psychedelic drug and a substituted Amphetamine. DOBU was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Known And Loved)'', only low dosages of 2–3 ...

****

DOC DOC, Doc, doc or DoC may refer to: In film and television * ''Doc'' (2001 TV series), a 2001–2004 PAX series * ''Doc'' (1975 TV series), a 1975–1976 CBS sitcom * "D.O.C." (''Lost''), a television episode * ''Doc'' (film), a 1971 Wester ...

**** DOEF ****

DOET 2,5-Dimethoxy-4-ethylamphetamine (DOET, DOE, Hecate) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin, and was described in his book '' PiHKAL'' (''Phenethylamines i Hav ...

, also known as 'DOE' **** DOI **** DOM, also known as 'STP' **** Ψ-DOM **** DON ****

DOPR 2,5-Dimethoxy-4-propylamphetamine (DOPR) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was a ...

**** DOiPR **** DOT, also known as 'Aleph' (Aleph-2, Aleph-4, Aleph-6, and Aleph-7) **** Meta-DOT **** Ortho-DOT **** DOTFM *** Phenylcyclopropylamine derivatives (technically not amphetamines) **** DMCPA ***

DMMDA 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book '' PiHKAL''. Shulgin listed the dosage ...

*** DMMDA-2 *** 2,5-dimethoxy-3,4-dimethylamphetamine, also known as 'Ganesha'; (G-3, G-4, G-5, and G-N) *** 4-methyl-2,5-dimethoxymethamphetamine, also known as 'Beatrice', 'MDO-D', and 'MDOM' *** 2,N-dimethyl-4,5-methylenedioxyamphetamine, also known as 'Madam-6' ***

Dimethoxyamphetamine Dimethoxyamphetamine (DMA) is a series of six lesser-known psychedelic drugs similar in structure to the three isomers of methoxyamphetamine and six isomers of trimethoxyamphetamine. The isomers are 2,3-DMA, 2,4-DMA, 2,5-DMA, 2,6-DMA, 3,4-DMA, and ...

(2,4-DMA, 2,5-DMA, and 3,4-DMA) ***

Trimethoxyamphetamine Trimethoxyamphetamines (TMAs) are a family of isomeric psychedelic hallucinogenic drugs. There exist six different TMAs that differ only in the position of the three methoxy groups: TMA, TMA-2, TMA-3, TMA-4, TMA-5, and TMA-6. The TMAs are analogs ...

(TMA-2, TMA-6) ***

Tetramethoxyamphetamine Tetramethoxyamphetamine, or 2,3,4,5-tetramethoxyamphetamine, is a lesser-known psychedelic drug and a substituted amphetamine. Tetramethoxyamphetamine was first synthesized by Alexander Shulgin. In his book '' PiHKAL (Phenethylamines i Have Know ...

*** Br-DragonFLY ***

TFMFly TFMFly is a compound related to psychedelic phenethylamines such as 2C-B-FLY and 2C-TFM. It was first reported in 2005 by a team at Purdue University led by David Nichols. It acts as a potent agonist at the 5HT2A serotonin receptor subtype, ...

*** 2-Bromo-4,5-methylenedioxyamphetamine *** 4-Bromo-3,5-dimethoxyamphetamine *** EEE *** EEM *** EME *** EMM ***

EDMA 3,4-Ethylenedioxy-''N''-methylamphetamine (EDMA) is an entactogen drug of the methamphetamine class. It is an analogue of MDMA where the methylenedioxy ring has been replaced by an ethylenedioxy ring. EDMA was first synthesized by Alexander ...

*** EIDA *** Ethyl-J, also known as 'EBDB' *** Methyl-J, also known as 'MDMB' ***

Ethyl-K ''N''-Ethyl-1,3-benzodioxolylpentanamine (EBDP; Ethyl-K; 3,4-methylenedioxy-''N''-ethyl-α-propylphenethylamine) is a psychoactive drug and member of the phenethylamine chemical class which acts as an entactogen, psychedelic, and stimulant. It ...

, also known as 'EBDP' ***

Methyl-K ''N''-Methyl-1,3-benzodioxolylpentanamine (MBDP; Methyl-K, UWA-091), also known as 3,4-methylenedioxy-α-propyl-''N''-methylphenethylamine, is a psychoactive drug of the phenethylamine chemical class. It is the ''N''-methyl analogue of 1,3- be ...

, also known as 'MBDP' and 'UWA-91' ***

IDNNA IDNNA (2,5-dimethoxy-4-iodo-''N,N''-dimethylamphetamine) is a lesser-known psychedelic drug and a substituted amphetamine. It is also the ''N,N''-dimethyl analog of DOI. IDNNA was first synthesized by Alexander Shulgin. In his book '' PiHKAL'', ...

***

Iris Iris most often refers to: *Iris (anatomy), part of the eye *Iris (mythology), a Greek goddess * ''Iris'' (plant), a genus of flowering plants * Iris (color), an ambiguous color term Iris or IRIS may also refer to: Arts and media Fictional ent ...

***

MDAI MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) ''in vitro'' and produces entacto ...

***

MDMAI 5,6-Methylenedioxy-''N''-methyl-2-aminoindane (MDMAI), is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a p ...

*** MDAT *** MDMAT *** MDAL *** MDBU ***

MDBZ Methylenedioxybenzylamphetamine, abbreviated MDBZ, and systematically named 3,4-methylenedioxy-''N''-benzylamphetamine, is a psychedelic drug. It is the ''N''-benzyl derivative of 3,4-methylenedioxyamphetamine (MDA). MDBZ was first synthesized by ...

*** MDDM *** MDIP *** MDMEOET *** MDMEO *** MDOH, also known as 'MDH' *** MDHOET *** MDPL *** MDCPM *** MDPR ***

MEDA Meda may refer to: Places * Meda de Mouros, a parish in Tábua Municipality, Portugal * Medas, a parish in Gondomar Municipality, Portugal * Meda-Ela, Sri Lanka * Međa (Leskovac), village in the municipality of Leskovac, Serbia * Meda, Lombardy, ...

***

MEM Mem (also spelled Meem, Meme, or Mim) is the thirteenth letter of the Semitic abjads, including Hebrew mēm , Aramaic Mem , Syriac mīm ܡ, Arabic mīm and Phoenician mēm . Its sound value is . The Phoenician letter gave rise to the Greek ...

*** Methyl-DMA *** MMDA, also known as '3-methoxy-MDA' (2T-MMDA-3a and 4T-MMDA-2) ***

MMDA-2 MMDA-2 (2-methoxy-4,5-methylenedioxyamphetamine) is a psychedelic drug of the amphetamine class. It is closely related to MMDA and MDA. Alexander Shulgin was likely the first to synthesize MMDA-2. In his book '' PiHKAL'', the dose is listed a ...

*** 5-Methyl-MDA *** MEE *** MME *** MPM ***

DiFMDA Difluoromethylenedioxyamphetamine (DiFMDA) is a substituted derivative of 3,4-methylenedioxyamphetamine (MDA), which was developed by Daniel Trachsel and coworkers, along with the corresponding fluorinated derivatives of MDMA, MDEA, BDB and MBDB, ...

***

5-APB 5-APB (abbreviation of "5-(2-aminopropyl)benzofuran"; see infobox for the correct IUPAC name) is an empathogenic psychoactive compound of the substituted benzofuran, substituted amphetamine and substituted phenethylamine classes. 5-APB and ot ...

***

6-APB 6-APB (6-(2-aminopropyl)benzofuran) is an empathogenic psychoactive compound of the substituted benzofuran and substituted phenethylamine classes. 6-APB and other compounds are sometimes informally called "Benzofury" in newspaper reports. It is ...

, also known as 'Benzofury' *** 5-APDB *** 6-APDB ***

5-MAPB 5-MAPB (1-(benzofuran-5-yl)-''N''-methylpropan-2-amine) is an entactogenic designer drug similar to MDMA in its structure and effects. Legal Status Canada 5-MAPB is not listed itself in the CDSA but since it is structurally related to MDMA it ...

*** 5-MAPDB *** 6-MAPDB, its psychedelic activity is disputed *** 6-MAPB *** 6-EAPB ***

5-EAPB 5-EAPB (1-(benzofuran-5-yl)-''N''-ethylpropan-2-amine) is a potentially entactogenic amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment o ...

***

Para-Methoxyamphetamine ''para''-Methoxyamphetamine (PMA), also known as 4-methoxyamphetamine (4-MA), is a designer drug of the amphetamine class with serotonergic effects. Unlike other similar drugs of this family, PMA does not produce stimulant, euphoriant, or enta ...

, also known as 'PMA' and '4-MA' ***

Paramethoxymethamphetamine ''para''-Methoxy-''N''-methylamphetamine (also known as PMMA, Red Mitsubishi), chemically known as methyl-MA, 4-methoxy-''N''-methylamphetamine, 4-MMA) or (4-PMDA, as listed to its original physical name) is a stimulant and psychedelic drug clo ...

, also known as 'PMMA', 'Methyl-MA', and '4-MMA' ***

4-Ethylamphetamine 4-Ethylamphetamine (4-EA) is a substituted amphetamine derivative which has been sold as a designer drug. It is mainly known as a synthetic intermediate used as a building block to manufacture larger molecules, but 4-EA is closely related in chem ...

, also known as '4-EA' ***

3-Methoxy-4-methylamphetamine 3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade.de Zorzi C, Cavalli A, U ...

, also known as 'MMA' ***

4-Methylmethamphetamine 4-Methylmethamphetamine (4-MMA) or Mephedrine, is a putative stimulant and entactogen drug of the amphetamine class. It is the β-de keto analogue of mephedrone. See also * 4-Methylamphetamine (4-MA) * 4-Methylmethcathinone (4-MMC) * 3- ...

, also known as '4-MMA' ***

4-Methylthioamphetamine 4-Methylthioamphetamine (4-MTA) is a designer drug of the substituted amphetamine class developed in the 1990s by a team led by David E. Nichols, an American pharmacologist and medical chemist, at Purdue University. It acts as a non-neurotoxic hi ...

, also known as '4-MTA' ***

4-Fluoroamphetamine 4-Fluoroamphetamine (4-FA; 4-FMP; PAL-303; "Flux"), also known as ''para''-fluoroamphetamine (PFA) is a psychoactive research chemical of the phenethylamine and substituted amphetamine chemical classes. It produces stimulant and entactogenic ef ...

, also known as '4-FA', 'PAL-303', 'Flux', 'Flits', 'R2D2', and 'Miley' ***

Norfenfluramine Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family that behaves as a serotonin and norepinephrine releasing agent and potent 5-HT2A, 5-HT2B, and 5-HT2C agonist. The action of norfenfluramine on ...

, also known as '3-TFMA' *** Para-Iodoamphetamine, also known as 'PIA', '4-iodoamphetamine', and '4-IA' *** Para-Chloroamphetamine, also known as 'PCA', '4-chloroamphetamine', and '4-CA' * Benzoxazines (more specifically cyclopropylethynylated benzoxazines) ** Substituted benzoxazines ***

Efavirenz Efavirenz (EFV), sold under the brand names Sustiva among others, is an antiretroviral medication used to treat and prevent HIV/AIDS. It is generally recommended for use with other antiretrovirals. It may be used for prevention after a needle ...

, the active constituent of Sustiva, Stocrin, and Efavir

Empathogens/entactogens ( serotonin (5-HT) releasing agents)

* Substituted methylenedioxy-phenethylamines ( MDxx) **

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desire ...

, also known as 'Molly', and 'Mandy' ** MDA, also known as 'Sass' **

2,3-MDA 2,3-Methylenedioxyamphetamine (2,3-MDA) or ORTHO-MDA is an amphetamine derivative which is mentioned in PIHKAL as a fairly potent and long-lasting stimulant drug, but with little or none of the entactogenic effects associated with its better- ...

, also known as 'ORTHO-MDA' ** 5-Methyl-MDA ** MMDA, also known as '3-methoxy-MDA' ** MDEA, also known as 'MDE' **

MBDB 1,3-Benzodioxolyl-''N''-methylbutanamine (''N''-methyl-1,3-benzodioxolylbutanamine, MBDB, 3,4-methylenedioxy-''N''-methyl-α-ethylphenylethylamine) is an entactogen of the phenethylamine chemical class. It is known by the street names Eden and ...

** MDAL ** MDBU **

** MDDM ** MDIP ** MDMEOET ** MDMEO ** MDOH, also known as 'MDH' ** MDHOET ** MDPL ** MDCPM ** MDPR ** BDB, also known as 'MDB' and 'J' **

** EIDA **

, also known as 'EBDP' **

†, also known as 'MMDPEA'; an active constituent of certain cacti, such as

and San Pedro * Substituted amphetamines (exclusively; most of the substituted methylenedioxy-phenethylamines also overlap this category) **

, also known as 'PMA' **

, also known as 'PMMA' and 'Methyl-MA' **

, also known as '4-EA' **

, also known as 'MMA' **

, also known as '4-MMA' **

, also known as '4-MTA' **

, also known as '4-FA', 'PAL-303', 'Flux', 'Flits', 'R2D2', and 'Miley' **

, also known as '3-TFMA' ** Para-Iodoamphetamine, also known as 'PIA', '4-iodoamphetamine', and '4-IA' ** Para-Chloroamphetamine, also known as 'PCA', '4-chloroamphetamine', and '4-CA' * Substituted cathinones **

Methylone Methylone (also known as "3,4-methylenedioxy-''N''-methylcathinone", "MDMC", "βk-MDMA" and by the slang term "M1") is an empathogen and stimulant psychoactive drug. It is a member of the substituted amphetamine, substituted cathinone and s ...

, also known as 'bk-MDMA' and 'MDMC' ** Ethylone, also known as 'bk-MDEA' and 'MDEC' **

Eutylone Eutylone (also known as β-keto-1,3-benzodioxolyl-''N''-ethylbutanamine, bk-EBDB, and ''N''-ethylbutylone) is a stimulant and empathogenic compound developed in the 1960s, which is classified as a designer drug. It was first reported to the EMC ...

, also known as 'bk-EBDB' **

Butylone Butylone, also known as β-keto-''N''-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine chemical class. It is the β-keto (substituted cathinone) analogue of MBDB and ...

, also known as 'bk-MBDB' **

Pentylone Pentylone (β-Keto-Methylbenzodioxolylpentanamine, βk-Methyl-K, βk-MBDP, methylenedioxypentedrone, or 1‐(3,4‐methylenedioxyphenyl)‐2‐(methylamino)pentan‐1‐one) is a stimulant developed in the 1960s. It is a substituted cathinone ...

, also known as 'bk-Methyl-K' and 'bk-MBDP' **

4-Ethylmethcathinone 4-Ethylmethcathinone (4-EMC) is a recreational designer drug of the stimulant and entactogen class. It is a structural isomer of 4-MEC and 3,4-DMMC. It has been identified in many countries around the world, initially in Europe but was first fo ...

, also known as '4-EMC' **

3-Methylmethcathinone 3-Methylmethcathinone, also known as 3-MMC and metaphedrone, is a designer drug from the substituted cathinone family. 3-MMC is closely related in structure to the more commonly known illicit drug mephedrone (4-MMC), and is also illegal in most ...

, also known as '3-MMC' * Substituted benzofurans **

** 5-APDB ** 6-APDB **

** 5-MAPDB ** 6-MAPDB, its psychedelic activity is disputed ** 6-MAPB **

** 6-EAPB ** 5-MBPB * Substituted tetralins ** MDAT ** MDMAT ** 6-CAT ** Tetralinylaminopropane, also known as 'TAP' and '6-APT' * Substituted indanes **

Trifluoromethylaminoindane 5-Trifluoromethyl-2-aminoindane (TAI) is a psychoactive drug and research chemical with putative entactogenic effects. It functions as a selective serotonin releasing agent (SSRA). TAI is the aminoindane analogue of norfenfluramine and is appr ...

, also known as 'TAI' ** Ethyltrifluoromethylaminoindane, also known as 'ETAI' ** 5-Iodo-2-aminoindane, also known as '5-IAI' **

MMAI 5-Methoxy-6-methyl-2-aminoindane (MMAI) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) and produces entactogen effects in ...

Indanylaminopropane 5-(2-Aminopropyl)-2,3-dihydro-1''H''-indene (5-APDI), also known as indanylaminopropane (IAP), IAP (psychedelic), 2-API(2-aminopropylindane), indanametamine, and, incorrectly, as indanylamphetamine, is an entactogen and psychedelic drug of the a ...

, also known as '5-APDI' and 'IAP' * Substituted naphthalenes ** Naphthylaminopropane, also known as 'NAP' and 'PAL-287' * Substituted phenylisobutylamines (alpha-ethyl-phenethylamines) ** 4-chlorophenylisobutylamine, also known as '4-chloro-α-ethylphenethylamine', '4-CAB', and 'AEPCA' ** 4-Methylphenylisobutylamine, also known as '4-MAB' **

, also known as 'α-Et-DOM', '4C-D', and 'Dimoxamine' * Alpha-substituted (-alkylated) tryptamines ** α-methyltryptamine, also known as 'αMT' and 'AMT' ** 5-MeO-αMT ** α-ethyltryptamine, also known as 'αET' and 'AET' ** 4-Me-αET ** 7-Me-αET ** 5-MeO-αET **

Cannabinoids ( CB-1 cannabinoid receptor ligands)

Phytocannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

** Δ⁹-THC†,

agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ag ...

; the primary active constituent of

cannabis ''Cannabis'' () is a genus of flowering plants in the family Cannabaceae. The number of species within the genus is disputed. Three species may be recognized: '' Cannabis sativa'', '' C. indica'', and '' C. ruderalis''. Alternative ...

*** 11-hydroxy-Δ⁹-THC, agonist; an

active metabolite An active metabolite is an active form of a drug after it has been processed by the body. Metabolites of drugs An active metabolite results when a drug is metabolized by the body into a modified form which continues to produce effects in the body ...

of orally administered Δ⁹-THC; not technically a phytocannabinoid ** CBD†,

negative allosteric modulator In pharmacology and biochemistry, allosteric modulators are a group of substances that bind to a receptor to change that receptor's response to stimulus. Some of them, like benzodiazepines, are drugs. The site that an allosteric modulator binds t ...

, another major active constituent of cannabis ** CBN†, a minor active constituent of cannabis, also a metabolite of THC and a product of its

degradation Degradation may refer to: Science * Degradation (geology), lowering of a fluvial surface by erosion * Degradation (telecommunications), of an electronic signal * Biodegradation of organic substances by living organisms * Environmental degradatio ...

THCV Tetrahydrocannabivarin (THCV, THV, O-4394, GWP42004) is a homologue of tetrahydrocannabinol (THC) having a propyl (3-carbon) side chain instead of a pentyl (5-carbon) group on the molecule, which makes it produce very different effects from THC. ...

†, a minor active constituent of cannabis * Synthetic cannabinoids **

(C6)-CP 47,497 (C6)-CP 47,497 (CP 47,497 dimethylhexyl homologue) is a synthetic cannabinoid Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plant ...

(C9)-CP 47,497 (C9)-CP 47,497 (CP 47,497 dimethylnonyl homologue) is a synthetic cannabinoid, a CP 47,497 homologue. Its systematic name is 2- 1''S'',3''R'')-3-hydroxycyclohexyl5-(1,1-dimethylnonyl)phenol. See also * Synthetic cannabis * (C6)-CP 47,497 * ...

** 1-Butyl-3-(2-methoxybenzoyl)indole ** 1-Butyl-3-(4-methoxybenzoyl)indole ** 1-Pentyl-3-(2-methoxybenzoyl)indole ** 2-Isopropyl-5-methyl-1-
(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene ** 4-HTMPIPO **

4-Nonylphenylboronic acid 4-Nonylphenylboronic acid is a potent and selective inhibitor of the enzyme fatty acid amide hydrolase (FAAH), with an IC50 of 9.1nM, and 870x selectivity for FAAH over the related enzyme MAGL, which it inhibits with an IC50 of 7900nM. It is al ...

** 5Br-UR-144 ** 5Cl-APINACA ** 5Cl-UR-144 ** 5F-3-pyridinoylindole ** 5F-AB-FUPPYCA ** 5F-ADB-PINACA ** 5F-ADBICA **

5F-ADB 5F-ADB (also known as 5F-MDMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products and has been sold online as a designer drug. 5F-AD ...

5F-AMB 5F-AMB (also known as 5F-MMB-PINACA and 5F-AMB-PINACA) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family, which has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan ...

5F-APINACA 5F-APINACA (also known as 5F-AKB-48 or 5F-AKB48) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Structurally it closely resembles cannabinoid compounds from patent WO 2003/035005 but with a 5-fluoropenty ...

** 5F-CUMYL-PINACA **

5F-EMB-PINACA 5F-EMB-PINACA (also known as 5F-AEB) is an indazole-based synthetic cannabinoid from the indazole-3-carboxamide family that has been sold online as a designer drug. It was first reported by the EMCDDA as part of a seizure of 149 grams of white p ...

** 5F-NNE1 **

5F-PB-22 5F-PB-22 (5F-QUPIC or quinolin-8-yl 1-pentyfluoro-1''H''-indole-3-8-carboxylate) is a designer drug which acts as a cannabinoid agonist. The structure of 5F-PB-22 appears to have been designed with an understanding of structure–activity relatio ...

** 5F-PCN ** 5F-PY-PICA ** 5F-PY-PINACA ** 5F-SDB-006 ** HHC **

A-796,260 A-796,260 is a drug developed by Abbott Laboratories that acts as a potent and selective cannabinoid CB2 receptor agonist. Replacing the aromatic 3-benzoyl or 3- naphthoyl group found in most indole derived cannabinoids with the 3- tetramethylcy ...

A-834,735 A-834,735 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors, with a ''K''i of 12 nM at CB1 and 0.21 nM at CB2. Replacing the aromatic 3-benzoyl or 3- ...

A-836,339 A-836,339 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist. It is selective for CB2, with ''K''i values of 0.64 nM at CB2 vs 270 nM at the psychoactive CB1 receptor, but while it exhi ...

** A-955,840 ** A-40174 ** A-41988 ** A-42574 ** AB-001 ** AB-CHFUPYCA ** AB-CHMFUPPYCA **

AB-CHMINACA AB-CHMINACA is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor (''K''i = 0.78 nM) and CB2 receptor (''K''i = 0.45 nM) and fully substitutes for Δ9-THC in rat discrimination st ...

AB-FUBICA AB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 21 nM at CB1 and 15 nM at CB2. See also * AB-FUBINACA AB-FUBINACA is a drug that acts as a potent agonist for the cannabinoid receptors, w ...

** AB-FUBINACA 2-fluorobenzyl isomer ** AB-FUBINACA ** AB-PICA **

AB-PINACA AB-PINACA is a compound that was first identified as a component of synthetic cannabis products in Japan in 2012. It was originally developed by Pfizer in 2009 as an analgesic medication. AB-PINACA acts as a potent agonist for the CB1 recept ...

** Abnormal cannabidiol ** ADAMANTYL-THPINACA **

ADB-CHMINACA ADB-CHMINACA (also known as MAB-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of ''K''i = 0.289 nM and was originally developed by Pfizer in 2009 as an ana ...

ADB-FUBICA ADB-FUBICA is a drug that acts as a potent agonist for the cannabinoid receptors, with EC50 values of 2.6 nM at CB1 and 3.0 nM at CB2. See also * AB-FUBICA * AB-FUBINACA * ADB-FUBINACA ADB-FUBINACA is a designer drug identified in synthetic ...

ADB-FUBINACA ADB-FUBINACA is a designer drug identified in synthetic cannabis blends in Japan in 2013. In 2018, it was the third-most common synthetic cannabinoid identified in drugs seized by the Drug Enforcement Administration. The (''S'')-enantiomer of A ...

ADB-PINACA ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB1 receptor and CB2 receptor with EC50 values of 0.52 nM and 0.88 nM respectively. Like MDMB-FUBINACA ...

** ADBICA ** ADSB-FUB-187 **

Ajulemic acid Ajulemic acid (1',1'-Dimethylheptyl-delta-8-tetrahydrocannabinol-11-oic acid) (DMH-D8-THC-11-OIC) (AB-III-56, HU-239, IP-751, CPL 7075, CT-3, JBT-101, Anabasum, Resunab, Lenabasum) is a synthetic cannabinoid that shows anti-fibrotic and anti-inf ...

AM-087 AM-087 (part of the AM cannabinoid series) is an analgesic drug which acts as a cannabinoid agonist. It is a derivative of Δ8-THC, substituted on the 3-position side chain. AM-087 is a potent CB1 agonist with a Ki of 0.43 nM, making it a ...

AM-411 AM-411 (part of the AM cannabinoid series) is an analgesic drug that is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with an adamantyl group at the 3-position, demonstrating that the binding pocket for the alkyl chain at this ...

AM-630 AM-630 (6-Iodopravadoline) is a drug that acts as a potent and selective inverse agonist for the cannabinoid receptor CB2, with a ''K''i of 32.1 nM at CB2 and 165x selectivity over CB1, at which it acted as a weak partial agonist. It is u ...

** AM-679 **

AM-694 AM-694 (1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole) is a designer drug that acts as a potent and selective agonist for the cannabinoid receptor CB1. It is used in scientific research for mapping the distribution of CB1 receptors. Pharmacology A ...

** AM-855 ** AM-883 **

AM-905 AM-905 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB1 and ...

AM-906 AM-906 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB1 and ...

** AM-919 ** AM-926 **

AM-938 AM-938 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid receptor agonist. It is a derivative of HU-210 which has been substituted with a 6β-(3-hydroxyprop-1-ynyl) group. This adds a "southern" aliphatic hydroxyl ...

AM-1220 AM-1220 is a drug that acts as a potent and moderately selective agonist for the cannabinoid receptor CB1, with around 19 times selectivity for CB1 over the related CB2 receptor. It was originally invented in the early 1990s by a team led by Th ...

AM-1221 AM-1221 is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB2, with a ''K''i of 0.28 nM at CB2 and 52.3 nM at the CB1 receptor, giving it around 180 times selectivity for CB2. The 2-methyl and 6-nitro ...

AM-1235 AM-1235 (1-(5-fluoropentyl)-3-(naphthalen-1-oyl)-6-nitroindole) is a drug that acts as a potent and reasonably selective agonist for the cannabinoid receptor CB1. Pharmacology Pharmacodynamics AM-1235 is a cannabinoid receptor agonist with Ki ...

** AM-1241 **

AM-1248 AM-1248 is a drug that acts as a moderately potent agonist for both the cannabinoid receptors CB1 and CB2, but with some dispute between sources over its exact potency and selectivity. Replacing the 3-(1-naphthoyl) group found in many indole de ...

** AM-1346 ** AM-1387 ** AM-1714 **

AM-2201 AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor. It is part of the AM series of cannabinoids discovered by Alexandros Makriyanni ...

AM-2232 AM-2232 (1-(4-cyanobutyl)-3-(naphthalen-1-oyl)indole) is a drug that acts as a potent but unselective agonist for the cannabinoid receptors, with a ''K''i of 0.28 nM at CB1 and 1.48 nM at CB2. In the United States, all CB1 receptor ...

AM-2233 AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a ''K''i of 1.8 nM at CB1 and 2.2 nM at CB2 as the active (''R'') enantiomer. It was developed as a selective radioligand for the cannab ...

AM-2389 AM-2389 is a classical cannabinoid derivative which acts as a potent and reasonably selective agonist for the CB1 receptor, with a ''K''i of 0.16 nM, and 26x selectivity over the related CB2 receptor. It has high potency in animal tests of ...

AM-4030 AM-4030 is an analgesic drug which is a cannabinoid receptor agonist. It is a derivative of HU-210 which has been substituted with a 6β-((E)-3-hydroxyprop-1-enyl) group. This adds a "southern" aliphatic hydroxyl group to the molecule as seen in ...

** AM-4113 ** AM-6527 **

AM-6545 AM-6545 is a drug which acts as a peripherally selective silent antagonist for the CB1 receptor, and was developed for the treatment of obesity. Other cannabinoid antagonists such as rimonabant have been marketed for this application, but have ...

** AM-251 ** AM-281 ** AM-404 ** AMB-CHMINACA **

AMB-FUBINACA AMB-FUBINACA (also known as FUB-AMB and MMB-FUBINACA) is an indazole-based synthetic cannabinoid that is a potent agonist for the cannabinoid receptors, with ''K''i values of 10.04 nM at CB1 and 0.786 nM at CB2 and EC50 values of 0. ...

** AMG-1 **

AMG-3 AMG-3 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8THC substituted with a dithiolane group on the 3-position side chain. AMG-3 is a potent agonist at both CB1 and CB2 recept ...

AMG-36 AMG-36 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8THC substituted with a cyclopentane Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with ...

AMG-41 AMG-41 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with a cyclopropyl group on the C1'-position of the C3-alkyl side chain. AMG-41 is a potent agonist at bot ...

** APICA **

APINACA APINACA (AKB48, ''N''-(1-adamantyl)-1-pentyl-1''H''-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors, with a Ki of 304.5nM and an EC50 of 585nM at CB1. It had never previously been report ...

, also known as 'AKB48' **

APP-FUBINACA APP-FUBINACA is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. Pharmacological testing showed APP-FUBINACA to have only moderate affinity for the CB1 receptor, with a Ki of 708 nM, while its EC50 was not te ...

** Arachidonoyl serotonin ** ACEA ** ACPA ** Arvanil ** AZ-11713908 ** BAY 38-7271 ** BAY 59-3074 ** BIM-018 ** Biochanin A **

BML-190 BML-190 (Indomethacin morpholinylamide) is a drug used in scientific research that acts as a selective CB2 inverse agonist. BML-190 is structurally derived from the NSAID indomethacin but has a quite different biological activity. The activity p ...

** Nabidrox (Canbisol) ** Cannabicyclohexanol ** Cannabipiperidiethanone ** CAY-10401 ** CAY-10429 ** CAY-10508 **

CB-13 CB-13 (CRA13, SAB-378) is a cannabinoid drug, which acts as a potent agonist at both the CB1 and CB2 receptors, but has poor blood–brain barrier penetration, and so produces only peripheral effects at low doses, with symptoms of central effec ...

** CB-25 ** CB-52 ** CB-86 ** CB-86 **

CBS-0550 CBS-0550 is a drug developed by Taisho Pharmaceutical, which acts as a potent and selective cannabinoid CB2 receptor agonist, with 1400x selectivity for CB2 over the related CB1 receptor. Unlike most cannabinoid agonists, CBS-0550 has good solu ...

CP 47,497 CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s. It has analgesic effects and is used in scientific research. It is a potent CB1 agonist with a ''K''d of 2.1 nM. Homologue On the 19th of ...

** CP 55,244 **

CP 55,940 55,940 is a synthetic cannabinoid which mimics the effects of naturally occurring THC (one of the psychoactive compounds found in cannabis). CP 55,940 was created by Pfizer in 1974 but was never marketed. It is currently used to study the endoca ...

** CUMYL-5F-PICA ** CUMYL-BICA ** CUMYL-PICA ** CUMYL-PINACA ** CUMYL-THPINACA **

Dexanabinol Dexanabinol (HU-211 or ETS2101) is a synthetic cannabinoid derivative in development by e-Therapeutics plc. It is the "unnatural" enantiomer of the potent cannabinoid agonist HU-210. Unlike other cannabinoid derivatives, HU-211 does not act as a ...

, also known as 'HU-211' **

Dimethylheptylpyran Dimethylheptylpyran (DMHP, 3-(1,2-dimethylheptyl)-Δ6a(10a)-THC, 1,2-dimethylheptyl-Δ3-THC, A-40824, or EA-2233) is a synthetic analog of THC, which was invented in 1949 during attempts to elucidate the structure of Δ9-THC, one of the act ...

, also known as 'DMHP' ** Drinabant, also known as 'AVE1625' **

Dronabinol The International Nonproprietary Name Dronabinol, also known as delta-9-tetrahydrocannabinol, or under the trade names Marinol, Syndros, Reduvo and Adversa, is a generic name for the molecule of delta-9-tetrahydrocannabinol in the pharmaceutic ...

EAM-2201 EAM-2201 (4'-ethyl-AM-2201, 5"-fluoro-JWH-210, SGT-14) is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by la ...

** EMB-FUBINACA **

FAB-144 FAB-144 is an indazole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is the indazole analogue of XLR-11. Legal status Sweden's public health agency sug ...

** FDU-NNE1 **

FDU-PB-22 FDU-PB-22 is a derivative of JWH-018 that is presumed to be a potent agonist of the CB1 receptor, and has been sold online as a designer drug. Pharmacology FDU-PB-22 acts as a full agonist with a binding affinity of 1.19nM at CB1 and 2.43nM at ...

FUB-144 FUB-144 (also known as FUB-UR-144) is an indole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is an analogue of UR-144 and XLR-11 where the pentyl chain ...

FUB-APINACA FUB-APINACA (also known as AFUBINACA and FUB-AKB48) is an indazole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is an analog of APINACA and 5F-APINACA whe ...

FUB-JWH-018 FUB-JWH-018 (also known as FUB-018) is a naphthoylindole-based synthetic cannabinoid, representing a molecular hybrid of JWH-018 and AB-FUBICA or ADB-FUBICA. Legal status In the United States, all CB1 receptor agonists of the 3-(1-naphthoyl)in ...

FUB-PB-22 FUB-PB-22 (QUFUBIC) is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug. Pharmacology FUB-PB-22 acts as a full agonist with a binding affinity of 0.386nM at CB1 and ...

FUBIMINA FUBIMINA (also known as BIM-2201, BZ-2201 and FTHJ) is a synthetic cannabinoid that is the benzimidazole analog of AM-2201 and has been used as an active ingredient in synthetic cannabis products. It was first identified in Japan in 2013, alo ...

Genistein Genistein (C15H10O5) is a naturally occurring compound that structurally belongs to a class of compounds known as isoflavones. It is described as an angiogenesis inhibitor and a phytoestrogen. It was first isolated in 1899 from the dyer's bro ...

** GW-405,833, also known as 'L-768,242' ** GW-842,166X **

Hemopressin Hemopressin (Hp) is an alpha hemoglobin fragment with the sequence PVNFKFLSH, originally identified in extracts of rat brain using an enzyme capture technique. It binds cannabinoid receptors, acting as an inverse agonist at CB1 receptors. Longer ...

HU-210 HU-210 is a synthetic cannabinoid that was first synthesized in 1988 from (1R,5S)-myrtenol by a group led by Raphael Mechoulam at the Hebrew University. HU-210 is 100 to 800 times more potent than natural THC from cannabis and has an extended d ...

HU-243 HU-243 (AM-4056) is a synthetic cannabinoid drug that is a single enantiomer of the hydrogenated derivative of the commonly used reference agonist HU-210. It is a methylene homologue of canbisol. It is a potent agonist at both the CB1 and CB ...

** HU-308 **

HU-320 HU-320 (7-nor-7-carboxy-CBD-1,1-DMH) is a drug related to cannabidiol, which has strong antiinflammatory and immunosuppressive properties while demonstrating no psychoactive effects. See also * 7-Hydroxycannabidiol * Ajulemic acid * HU-210 H ...

HU-331 HU-331 is a quinone anticarcinogenic drug synthesized from cannabidiol, a cannabinoid in the ''Cannabis sativa'' plant. It showed a great efficacy against oncogenic human cells. HU-331 does not cause arrest in cell cycle, cell apoptosis or caspas ...

HU-336 HU-336 is a strongly antiangiogenic compound, significantly inhibiting angiogenesis at concentrations as low as 300 nM. It inhibits angiogenesis by directly inducing apoptosis of vascular endothelial cells without changing the expression of ...

HU-345 HU-345 (cannabinol quinone) is a drug that is able to inhibit aortic ring angiogenesis more potently than its parent compound cannabinol (CBN). It exhibits no psychoactive effects on the body. HU-345 can be derived through the oxidative degra ...

** HU-910 ** Ibipinabant, also known as 'SLV319' **

IDFP IDFP is an organophosphorus compound related to the nerve agent sarin. Like sarin, IDFP is an irreversible inhibitor for a number of different enzymes that normally serve to break down neurotransmitters, however the long alkyl chain of IDFP mak ...

** JNJ 1661010 ** JTE-907 **

JTE 7-31 JTE 7-31 is a selective cannabinoid receptor agonist invented by Japan Tobacco. It is a reasonably highly selective CB2 agonist, but still retains appreciable affinity at CB1, with a Ki of 0.088nM at CB2 vs 11nM at CB1. Legality JTE 7-31 is il ...

JWH-007 JWH-007 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It was first reported in 1994 by a group including the noted cannabinoid chemist John W. Huffman. It was t ...

JWH-015 JWH-015 is a chemical from the naphthoylindole family that acts as a subtype-selective cannabinoid agonist. Its affinity for CB2 receptors is 13.8 nM, while its affinity for CB1 is 383 nM, meaning that it binds almost 28 times more strongly to ...

JWH-018 JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in ...

JWH-019 JWH-019 is an analgesic chemical from the naphthoylindole family that acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is the ''N''-hexyl homolog of the more common synthetic cannabinoid compound JWH-018. Unlike the butyl hom ...

JWH-030 JWH-030 is a research chemical which is a cannabinoid receptor agonist. It has analgesic effects and is used in scientific research. It is a partial agonist at CB1 receptors, with a Ki of 87 nM, making it roughly half the potency of THC. It ...

** JWH-051 ** JWH-073 **

JWH-081 JWH-081 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. With a Ki of 1.2nM it is fairly selective for the CB1 subtype, its affinity at this subtype is measured at ...

** JWH-098 **

JWH-116 JWH-116 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the indole 2-ethyl derivative of related compound JWH-018. The binding affinity of JWH-116 for the CB1 receptor is reported as Ki = 52 ± 5 nM. In the Unit ...

JWH-122 JWH-122 is a synthetic cannabimimetic that was discovered by John W. Huffman. It is a methylated analogue of JWH-018. It has a Ki of 0.69 nM at CB1 and 1.2 nM at CB2. In January 2015, over 40 people were reportedly sickened after eating a holid ...

** JWH-133 ** JWH-139 **

JWH-147 JWH-147 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 11.0 nM at CB1 vs 7.1 nM at CB2. It was disco ...

** JWH-149 ** JWH-161 ** JWH-164 ** JWH-167 ** JWH-175 ** JWH-176 ** JWH-182 **

JWH-184 JWH-184 is a synthetic cannabinoid receptor ligand from the naphthylmethylindole family. It is the carbonyl-reduced derivative of related compound JWH-122. The binding affinity of JWH-184 for the CB1 receptor is reported as Ki = 23 ± 6 nM. In ...

JWH-185 JWH-185 is a synthetic cannabinoid receptor ligand from the naphthoylindole family. It is the carbonyl-reduced derivative of related compound JWH-081. The binding affinity of JWH-185 for the CB1 receptor is reported as Ki = 17 ± 3 nM. In the ...

** JWH-192 **

JWH-193 JWH-193 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-193 has a binding affinity at the CB1 r ...

** JWH-194 ** JWH-195 **

JWH-196 JWH-196 is a synthetic cannabinoid receptor ligand from the naphthylmethylindole family. It is the indole 2-methyl derivative of related compound JWH-175, and the carbonyl reduced analog of JWH-007. The binding affinity of JWH-196 for the CB1 r ...

** JWH-197 **

JWH-198 JWH-198 is a drug from the aminoalkylindole and naphthoylindole families which acts as a cannabinoid receptor agonist. It was invented by the pharmaceutical company Sanofi-Winthrop in the early 1990s. JWH-198 has a binding affinity at the CB1 re ...

** JWH-199 **

JWH-200 JWH-200 (WIN 55,225) is an analgesic chemical from the aminoalkylindole family that acts as a cannabinoid receptor agonist. Its binding affinity, ''K''i at the CB1 receptor is 42 nM, around the same as that of THC, but its analgesic potenc ...

** JWH-203 ** JWH-210 ** JWH-229 ** JWH-249 ** JWH-250 ** JWH-251 ** JWH-302 **

JWH-307 JWH-307 is an analgesic drug used in scientific research, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It is somewhat selective for the CB2 subtype, with a Ki of 7.7 nM at CB1 vs 3.3 nM at CB2. It was disco ...

** JWH-359 ** JWH-369 ** JWH-370 **

JWH-398 JWH-398 is an analgesic chemical from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors. It has mild selectivity for CB1 with a Ki of 2.3 nM and 2.8 nM at CB2. This synthetic chemical comp ...

JWH-424 JWH-424 is a drug from the naphthoylindole family, which acts as a cannabinoid agonist at both the CB1 and CB2 receptors, but with moderate selectivity for CB2, having a Ki of 5.44nM at CB2 vs 20.9 nM at CB1. The heavier 8- iodo analogue ...

** JZL184 ** JZL195 **

Kaempferol Kaempferol (3,4′,5,7-tetrahydroxyflavone) is a natural flavonol, a type of flavonoid, found in a variety of plants and plant-derived foods including kale, beans, tea, spinach, and broccoli. Kaempferol is a yellow crystalline solid with a meltin ...

KM-233 KM-233 is a synthetic cannabinoid drug which is a structural analog of Δ8-tetrahydrocannabinol (THC), the less active but more stable isomer of the active component of ''Cannabis''. KM-233 differs from Δ8-THC by the pentyl side chain being ...

** L-759,633 ** L-759,656 ** LASSBio-881 ** LBP-1 ** Leelamine **

Levonantradol Levonantradol (CP 50,556-1) is a synthetic cannabinoid analog of dronabinol (Marinol) developed by Pfizer in the 1980s. It is around 30x more potent than THC, and exhibits antiemetic and analgesic effects via activation of CB1 and CB2 cannabin ...

, also known as 'CP 50,5561' ** LH-21 ** LY-320,135 **

LY-2183240 LY-2183240 is a drug which acts both as a potent inhibitor of the reuptake of the endocannabinoid anandamide and as an inhibitor of fatty acid amide hydrolase (FAAH), the primary enzyme responsible for degrading anandamide. This leads to markedly ...

** MAM-2201 ** MDA-7 **

MDA-19 MDA-19 (also known as BZO-HEXOXIZID) is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB2, with reasonable selectivity over the psychoactive CB1 receptor, though with some variation between species. In animal st ...

** MDA-77 **

MDMB-CHMICA MDMB-CHMICA is an indole-based synthetic cannabinoid that is a potent agonist of the CB1 receptor and has been sold online as a designer drug. While MDMB-CHMICA was initially sold under the name "MMB-CHMINACA", the compound corresponding to this ...

MDMB-CHMINACA MDMB-CHMINACA (also known as MDMB(N)-CHM) is an indazole-based synthetic cannabinoid that acts as a potent agonist of the CB1 receptor, and has been sold online as a designer drug. It was invented by Pfizer in 2008, and is one of the most potent ...

** MDMB-FUBINACA ** Menabitan ** MEPIRAPIM ** Methanandamide, also known as 'AM-356' ** MJ-15 ** MK-9470 ** MMB-2201 **

MN-18 MN 18 is an indazole-based synthetic cannabinoid that is an agonist for the cannabinoid receptors, with ''K''i values of 45.72 nM at CB1 and 11.098 nM at CB2 and EC50 values of 2.028 nM at CB1 and 1.233 nM at CB2, and has ...

MN-25 MN-25 (UR-12) is a drug invented by Bristol-Myers Squibb, that acts as a reasonably selective agonist of peripheral cannabinoid receptors. It has moderate affinity for CB2 receptors with a ''K''i of 11 nM, but 22x lower affinity for the p ...

, also known as 'UR-12' ** Nabazenil ** Nabilone ** Nabitan ** Naboctate ** NESS-0327 ** NESS-040C5 ** NIDA-41020 ** NM-2201 ** NMP-7 ** NNE1 ** Nonabine ** O-224 ** O-581 ** O-585 ** O-606 ** O-689 **

O-774 O-774 is a classical cannabinoid derivative which acts as a potent agonist for the cannabinoid receptors, with a ''K''i of 0.6 nM at CB1, and very potent cannabinoid effects in animal studies. See also * AM-2232 * O-1057 * O-1812 O-1812 ...

** O-806 ** O-823 ** O-889 **

O-1057 O-1057 is an analgesic cannabinoid derivative created by Organix Inc., Newburyport, Massachusetts, for use in scientific research. Unlike most cannabinoids discovered to date, it is water-soluble, which gives it considerable advantages over many ...

** O-1125 ** O-1184 ** O-1191 ** O-1238 ** O-1248 **

O-1269 O-1269 is a drug that is a diarylpyrazole derivative, related to potent cannabinoid antagonist drugs such as rimonabant and surinabant. However O-1269 and several related drugs were unexpectedly found to act as full or partial agonists at the ...

** O-1270 ** O-1376 ** O-1399 ** O-1422 ** O-1601 ** O-1602 ** O-1624 **

O-1656 O-1656 is a cannabinoid agonist which was invented by Billy R Martin and Raj K Razdan at Organix Inc in 2002. It is moderately selective for the CB2 receptor with a CB1 receptor affinity of 18 nM and a CB2 receptor affinity of 2 nM. Since it ha ...

** O-1657 ** O-1660 **

O-1812 O-1812 is an eicosanoid derivative related to anandamide that acts as a potent and highly selective agonist for the cannabinoid receptor CB1, with a ''K''i of 3.4 nM at CB1 and 3870 nM at CB2. Unlike most related compounds, O-1812 i ...

** O-1860 ** O-1861 ** O-1871 **

O-1918 O-1918 is a synthetic compound related to cannabidiol, which is an antagonist at two former orphan receptors GPR18 and GPR55, that appear to be related to the cannabinoid receptors. O-1918 is used in the study of these receptors, which have been ...

** O-2048 ** O-2050 ** O-2093 ** O-2113 ** O-2220 ** O-2365 ** O-2372 ** O-2373 ** O-2383 ** O-2426 ** O-2484 ** O-2545 ** O-2654 ** O-2694 ** O-2715 ** O-2716 ** O-3223 ** O-3226 **

Oleoylethanolamide Oleoylethanolamide (OEA) is an endogenous peroxisome proliferator-activated receptor alpha ( PPAR-α) agonist. It is a naturally occurring ethanolamide lipid that regulates feeding and body weight in vertebrates ranging from mice to pythons. OEA ...

, also known as 'OEA' ** Olvanil ** Org 27569 ** Org 27759 ** Org 28312 ** Org 28611 ** Org 29647 ** Otenabant, also known as 'CP-945,598' **

Palmitoylethanolamide Palmitoylethanolamide (PEA) is an endogenous fatty acid amide, and lipid modulator PEA has been studied in ''in vitro'' and ''in vivo'' systems using exogenously added or dosed compound; there is evidence that it binds to a nuclear receptor, thr ...

, also known as 'PEA' **

Parahexyl Parahexyl (Synhexyl, n-hexyl-Δ3-THC, (C6)-Δ6a(10a)-THC) is a synthetic homologue of THC which was invented in 1941 during attempts to elucidate the structure of Δ9-THC, one of the active components of cannabis. Parahexyl is similar in both st ...

** PF-03550096 ** PF-04457845 ** PF-622 ** PF-750 ** PF-3845 ** PF-514273 ** PHOP ** PipISB ** Pirnabine **

Pravadoline Pravadoline (WIN 48,098) is an antinflammatory and analgesic drug with an IC50 of 4.9 μM and a ''K''i of 2511 nM at CB1, related in structure to nonsteroidal anti-inflammatory drugs (NSAIDs) such as indometacin. It was developed in ...

Pregnenolone Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocor ...

PSB-SB-487 PSB-SB-487 is a coumarin derivative which is an antagonist at the former orphan receptor GPR55. Unlike older GPR55 antagonists such as O-1918, PSB-SB-487 has good selectivity over the related receptor GPR18, with an IC50 of 113nM at GPR55 vs 1250 ...

PSB-SB-1202 PSB-SB-1202 is a coumarin derivative which is an agonist at the cannabinoid receptors CB1 and CB2, with a CB1 Ki of 32nM and a CB2 Ki of 49nM. It is also a weak antagonist at the related receptor GPR55, with an IC50 of 6350nM, but has no signif ...

** PTI-1 ** PTI-2 ** PX-1 **

PX-2 PX-2 (also known as 5F-APP-PINACA, FU-PX and PPA(N)-2201) is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. It contains a phenylalanine amino acid amide as part of its structure. Legality Sweden's public he ...

PX-3 PX-3 (also known as APP-CHMINACA) is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of ''K''i = 47.6 nM and was originally developed by Pfizer in 2009 as an analgesic m ...

QUCHIC QUCHIC (BB-22, SGT-32 or 1-(cyclohexylmethyl)-1''H''-indole-3-carboxylic acid 8-quinolinyl ester) is a designer drug offered by online vendors as a cannabimimetic agent, and was first detected being sold in synthetic cannabis products in Japan i ...

, also known as 'BB-22' **

QUPIC PB-22 (QUPIC, SGT-21 or 1-pentyl-1''H''-indole-3-carboxylic acid 8-quinolinyl ester) is a designer drug offered by online vendors as a cannabimimetic agent, and detected being sold in synthetic cannabis products in Japan in 2013. PB-22 represen ...

, also known as 'PB-22' **

RCS-4 RCS-4, or 1-pentyl-3-(4-methoxybenzoyl)indole, is a synthetic cannabinoid drug sold under the names SR-19, BTM-4, or Eric-4 (later shortened to E-4), but originally, OBT-199. Pharmacology RCS-4 is a potent cannabinoid receptor agonist, with EC ...

** RCS-8 **

Rimonabant Rimonabant (also known as SR141716; trade names Acomplia, Zimulti) is an anorectic antiobesity drug that was first approved in Europe in 2006 but was withdrawn worldwide in 2008 due to serious psychiatric side effects; it was never approved in t ...

, also known as 'SR141716' ** Rosonabant, also known as 'E-6776' ** RTI-371 ** S-444,823 ** SDB-006 **

SER-601 SER-601 (COR-167) is a drug which acts as a potent and selective cannabinoid CB2 receptor agonist, based on a quinolone-3-carboxylic acid core structure, with 190 times selectivity for CB2 over the related CB1 receptor. It has analgesic An ...

** SPA-229 **

SR-144,528 SR144528 is a drug that acts as a potent and highly selective CB2 receptor inverse agonist, with a Ki of 0.6 nM at CB2 and 400 nM at the related CB1 receptor. It is used in scientific research for investigating the function of the CB2 ...

STS-135 STS-135 ( ISS assembly flight ULF7) was the 135th and final mission of the American Space Shuttle program. It used the orbiter ''Atlantis'' and hardware originally processed for the STS-335 contingency mission, which was not flown. STS-135 la ...

Surinabant Surinabant (SR147778) is a cannabinoid receptor type 1 antagonist developed by Sanofi-Aventis. It is being investigated as a potential treatment for nicotine addiction, to assist smoking cessation. It may also be developed as an anorectic drug ...

, also known as 'SR147778' **

Taranabant Taranabant (codenamed MK-0364) is a cannabinoid receptor type 1 (CB1) inverse agonist that was investigated as a potential treatment for obesity due to its anorectic effects. It was discovered by Merck & Co. In October 2008, Merck has stopped ...

, also known as 'MK-0364' ** Tedalinab ** THC-O-acetate ** THC-O-phosphate ** THJ-018 **

THJ-2201 THJ-2201 is an indazole-based synthetic cannabinoid that presumably acts as a potent agonist of the CB1 receptor and has been sold online as a designer drug. It is a structural analog of AM-2201 in which the central indole ring has been rep ...

** Tinabinol ** TM-38837 ** UR-144 ** URB-447 ** URB447, URB-447 ** URB597, URB-597 ** URB602, URB-602 ** URB754, URB-754 ** VCHSR ** VDM-11 ** VSN-16 ** WIN 54,461 ** WIN 55,212-2 ** WIN 56,098 ** XLR-11 (drug), XLR-11 ** Yangonin

Other

* Harmaline†, harmala alkaloids†, and other beta-carbolines, active constituents of

; powerful MAOIs (can be classified as indoles) * Salvinorin A†, an opioid (κ-opioid receptor agonist), the active constituent of ''Salvia divinorum'' sage * Salvinorin B methoxymethyl ether†, a semi-synthetic analogue of the natural product salvinorin A with longer duration and increased affinity and potency at the κ-opioid receptor * Salvinorin B ethoxymethyl ether†, a semi-synthetic analogue of the natural product salvinorin A with longer duration and increased affinity and potency at the κ-opioid receptor * Piperazines, such as pFPP and TFMPP, usually classified as stimulants * Myristicin† and elemicin†, the active constituents of nutmeg * Cryogenine (Vertine)†, the active constituent of certain ''Heimia'' species * Atropine†, Hyoscine hydrobromide, scopolamine†, and hyoscyamine†, the active constituents of certain Solanaceae species * Ibotenic acid† and muscimol†, the active constituents of ''Amanita muscaria'' mushrooms

References

{{Reflist Psychedelic drugs, . Drug-related lists, Psychedelic drugs

Serotonergic psychedelics ( serotonin 5-HT2A receptor agonists)

Empathogens/entactogens ( serotonin (5-HT) releasing agents)

Cannabinoids ( CB-1 cannabinoid receptor ligands)

Other

See also

References

Serotonergic psychedelics ( serotonin 5-HT_2A receptor agonists)