Psychedelic phenethylamines

3,4-Methylenedioxymethamphetamine (MDMA), commonly known as ecstasy (tablet form), and molly (crystal form), is an entactogen with stimulant and minor psychedelic properties.

2C-B, also known as 4-bromo-2,5-dimethoxyphenethylamine or by names such as Nexus or Erox, is a psychedelic drug of the phenethylamine and 2C families. The drug is used as a recreational drug and is usually taken orally. 2C-B produces hallucinogenic, mild stimulant, and mild entactogenic-like effects. Its hallucinogenic effects at typical doses are milder than those of other psychedelics like LSD or psilocybin.

3,4-Methylenedioxyamphetamine (MDA) is an entactogen, stimulant, and psychedelic drug of the amphetamine and MDxx families that is encountered mainly as a recreational drug. It is usually taken orally.

2C-I, also known as 4-iodo-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

Lorcaserin, marketed under the brand name Belviq, was a weight-loss drug developed by Arena Pharmaceuticals. It reduces appetite by activating the 5-HT2C serotonin receptor in the hypothalamus, a region of the brain which is known to control appetite. It was approved in 2012, and in 2020 was removed from the market in the United States due to an increased risk of cancer detected in users of Belviq.

Fenfluramine, sold under the brand name Fintepla, is a serotonergic medication used for the treatment of seizures associated with Dravet syndrome and Lennox–Gastaut syndrome. It was formerly used as an appetite suppressant in the treatment of obesity, but was discontinued for this use due to cardiovascular toxicity before being repurposed for new indications. Fenfluramine was used for weight loss both alone under the brand name Pondimin and in combination with phentermine commonly known as fen-phen.

2,5-Dimethoxy-4-methylamphetamine (DOM), also known as STP (standing for "Serenity, Tranquility, and Peace" and other phrases), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It has stimulant and antidepressant-like effects at low doses and hallucinogenic effects at higher doses. The drug can have a very slow onset and long duration, with its duration possibly being up to a few days at high doses. It is usually taken orally.

'''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 entactogenic effects, and behaves more like an antidepressant in comparison, though it does have some psychedelic properties.

2C-E, also known as 4-ethyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

25I-NBOMe, also known as 2C-I-NBOMe, Cimbi-5, and shortened to "25I", is a psychedelic drug of the phenethylamine, 2C, and NBOMe (25-NB) families. Since 2010, it has circulated in the recreational drug scene, often misrepresented as LSD. It is the most well-known member of the 25-NB family and the earliest member to be encountered as a novel recreational drug.

2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is little-used recreationally, but is widely used in scientific research in the study of psychedelics and serotonin receptors. The drug is taken orally.

PiHKAL: A Chemical Love Story, also known as Phenethylamines I Have Known and Loved, is a book by Alexander Shulgin and Ann Shulgin published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or entactogens. The book has two halves, with the second part containing detailed entries on 179phenethylamines. PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).

2C-D, also known as 4-methyl-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It has an unusually wide and gradual dose range and at low doses produces claimed cognitive enhancer-like effects, mild stimulant effects, and mild perceptual effects, whereas at high doses, it produces robust psychedelic effects. The drug is taken orally.

Bromo-DragonFLY, also known as DOB-DragonFLY (DOB-DFLY), is a psychedelic drug of the phenethylamine, DOx, and FLY families. It is taken orally. The drug has a delayed onset of up to 6hours and a very long duration of up to 1 to 3days.

2C-P, also known as 4-propyl-2,5-dimethoxyphenethylamine or as Selene, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally and is among the most potent and long-lasting of the 2C psychedelics.

2C-T-2, also known as 4-ethylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

Allylescaline (AL), or allylmescaline, also known as 4-allyloxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is taken orally.

Norfenfluramine, or 3-trifluoromethylamphetamine, is a never-marketed drug of the amphetamine family and a major active metabolite of the appetite suppressants fenfluramine and benfluorex. The compound is a racemic mixture of two enantiomers with differing activities, dexnorfenfluramine and levonorfenfluramine.

2C-B-FLY is a psychedelic and designer drug of the phenethylamine, 2C, and FLY families. It was first described in 1995 by Aaron Monte, Professor of Chemistry at UW-La Crosse.

chemical compound

group of stereoisomers

2,5-Dimethoxy-4-chloroamphetamine (DOC) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is taken orally.

Proscaline, also known as 4-propoxy-3,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is taken orally.

2C-T-7, also known as 4-propylthio-2,5-dimethoxyphenethylamine or as Blue Mystic or 7th Heaven, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

MMDA-2, also known as 2-methoxy-4,5-methylenedioxyamphetamine or as 6-methoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families. It is the 6-methoxy derivative of MDA and is a positional isomer of MMDA (5-methoxy-MDA).

3,4-Dimethoxyphenethylamine (DMPEA or 3,4-DMPEA), also known as homoveratrylamine, 3-desmethoxymescaline, or '''O,O-dimethyldopamine''', is a chemical compound of the phenethylamine family. It is an analogue of the major human neurotransmitter dopamine where the 3- and 4-position hydroxy groups have been replaced with methoxy groups. It is also closely related to mescaline (3,4,5-trimethoxyphenethylamine; 3,4,5-TMPEA) and to 3,4-dimethoxyamphetamine (3,4-DMA).

Escaline (E), also known as 3,5-dimethoxy-4-ethoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the 4-ethoxy analogue of mescaline (3,4,5-trimethoxyphenethylamine) and the phenethylamine (non-α-methyl) analogue of 3C-E (3,5-dimethoxy-4-ethoxyamphetamine). The drug has been encountered as a novel designer drug.

2C-G, or 2C-G-0, also known as 3,4-dimethyl-2,5-dimethoxyphenethylamine or as 3-methyl-2C-D, is a psychedelic phenethylamine of the 2C family. First synthesized by Alexander Shulgin, it has structural and pharmacodynamic properties similar to 2C-D and Ganesha (G). The drug has a number of known homologues, which are known as the 2C-G series of compounds.

2C-TFM, also known as 4-trifluoromethyl-2,5-dimethoxyphenethylamine or as 2C-CF3, is a serotonin 5-HT2 receptor agonist and psychedelic drug of the phenethylamine and 2C families. It was first synthesized in the laboratory of David E. Nichols. Later, it was tested in humans and its psychedelic effects were confirmed. 2C-TFM is the most potent psychedelic of the 2C psychedelics.

lesser-known psychedelic drug

chemical compound

3,4,5-Trimethoxyamphetamine (TMA, TMA-1, or 3,4,5-TMA), also known as α-methylmescaline (3C-mescaline or 3C-M) or mescalamphetamine, is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the trimethoxyamphetamine (TMA) series of positional isomers. The drug is notable in being the amphetamine (α-methylated) analogue of mescaline (3,4,5-trimethoxyphenethylamine).

6-APB, also known as 6-(2-aminopropyl)benzofuran, is an entactogen of the phenethylamine, amphetamine, and benzofuran families. 6-APB and related drugs are sometimes informally called "Benzofury" in media reports. It is similar in structure to MDA, but differs in that the 3,4-methylenedioxyphenyl ring system has been replaced with a benzofuran ring. 6-APB is also the unsaturated benzofuran derivative of 6-APDB. It may appear as a tan or brown grainy powder.

'3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH, MDH), also known as N-hydroxy-MDA', is an entactogen, psychedelic, and stimulant of the phenethylamine, amphetamine, and MDxx families. It is the N-hydroxy homologue of MDA, and the N-desmethyl homologue of FLEA (MDMOH).

DOET, also known as 4-ethyl-2,5-dimethoxyamphetamine or as Hecate, is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. It is closely related to DOM and is a synthetic analogue of the naturally occurring phenethylamine psychedelic mescaline. The drug is the derivative of DOM in which the methyl group at the 4 position has been replaced with a ethyl group. It is taken orally. DOET has a slow onset of 1 to 3hours, a delayed peak of 3 to 5hours, and a dose-dependent and potentially very long duration of 5 to 20hours.

chemical compound

2C-T, or 2C-T-1, also known as 4-methylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally. The drug has a relatively short duration and is of relatively low potency among the 2C psychedelics.

Lophophine, also known as 2C-MMDA-1, 5-methoxy-MDPEA, or 3-methoxy-4,5-methylenedioxyphenethylamine (MMDPEA or MMDPEA-1), is a psychedelic drug of the methylenedioxyphenethylamine family. It is the α-demethylated homologue of MMDA, and is also closely related to mescaline (3,4,5-trimethoxyphenethylamine) and MDPEA. Lophophine has been encountered as a novel designer drug.

2CBFly-NBOMe, also known as NBOMe-2C-B-FLY or as Cimbi-31, is a serotonin receptor modulator of the phenethylamine, DOx, and FLY families. It was indirectly derived from the phenethylamine hallucinogen 2C-B is and related to benzodifurans like 2C-B-FLY and N-benzylphenethylamines like 25B-NBOMe.

5-Methyl-MDA, also known as 5-methyl-3,4-methylenedioxyamphetamine, is an entactogen and psychedelic designer drug of the amphetamine class. It is a ring-methylated homologue of MDA and a structural isomer of MDMA.

2C-N, also known as 4-nitro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

Isoproscaline or 4-isopropoxy-3,5-dimethoxyphenethylamine is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is closely related to proscaline and was first synthesized by David E. Nichols and colleagues. The drug is taken orally.

2C-O, also known as 2,4,5-trimethoxyphenethylamine (2,4,5-TMPEA) or TMPEA-2, is a serotonin receptor modulator of the phenethylamine and 2C families related to the psychedelic drug mescaline. It is a positional isomer of mescaline (3,4,5-trimethoxyphenethylamine) and is the α-desmethyl analogue of 2,4,5-trimethoxyamphetamine (TMA-2). The drug is the parent compound of the 2C-O series of drugs. 2C-O appears to be inactive in terms of psychoactive effects in humans, at least at doses that have been assessed. In any case, it is a low-potency full agonist of the serotonin 5-HT2 receptors in vitro,

25B-NBOMe, also known as NBOMe-2C-B, Cimbi-36, or as '''N-(2-methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine', is a psychedelic drug of the phenethylamine, 2C, and 25-NB (NBOMe) families. It is the N''-(2-methoxybenzyl) derivative of 2C-B. The drug is taken sublingually, bucally, or intranasally.

2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA or DMMDA-1) is a lesser-known psychedelic drug of the amphetamine and MDxx families related to MMDA. It was first synthesized by Alexander Shulgin in the 1960s and was described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

2C-Se, also known as 4-methylseleno-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It was originally named by Alexander Shulgin as described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved). Shulgin listed its dose as perhaps 100mg orally and its duration as 6 to 8hours. Its onset was 45minutes, peak effects occurred after 1.5hours, and doses of 50 to 70mg orally produced threshold effects. Shulgin considered 2C-Se to be around three times the potency of mescaline, but was too concerned about toxicity to test it extensively, though he

3C-E, also known as 4-ethoxy-3,5-dimethoxyamphetamine or as α-methylescaline (3C-escaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of escaline.

2C-T-17, also known as '4-sec-butylthio-2,5-dimethoxyphenethylamine or as Nimitz', is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

Thiobuscaline (TB), or 4-thiobuscaline (4-TB), also known as 3,5-dimethoxy-4-butylthiophenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to the psychedelic drug mescaline. It is the analogue of buscaline in which the butoxy group at the 4 position has been replaced with a butylthio group.

DMMDA-2, also known as 2,3-dimethoxy-4,5-methylenedioxyamphetamine or as 5,6-dimethoxy-MDA, is a psychedelic drug of the phenethylamine, amphetamine, and MDxx families related to MDA. It is the derivative of MDA with methoxy groups at the 5 and 6 positions and of MMDA and MMDA-2 with an additional methoxy group at either of these positions.

2C-T-8, also known as 4-cyclopropylmethylthio-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families.

Asymbescaline (ASB), also known as 3,4-diethoxy-5-methoxyphenethylamine, is a psychedelic drug of the phenethylamine and scaline families related to mescaline. It is the analogue of mescaline in which the methoxy groups at the 3 and 4 positions have been replaced with ethoxy groups.

2C-F, also known as 4-fluoro-2,5-dimethoxyphenethylamine, is a psychedelic drug of the phenethylamine and 2C families. It is taken orally.

2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine (DOEF) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families.

chemical compound

HOT-2, also known as '4-ethylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-2', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-2. The drug is taken orally.

3C-BZ, also known as 4-benzyloxy-3,5-dimethoxyamphetamine or as α-methylbenzscaline (3C-benzscaline), is a psychedelic drug of the phenethylamine, amphetamine, and 3C families related to 3,4,5-trimethoxyamphetamine (TMA). It is the amphetamine (3C) analogue of benzscaline. The drug was first synthesized by Alexander Shulgin and described in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).

6-Methyl-MDA, also known as 6-methyl-3,4-methylenedioxyamphetamine is an entactogen and psychedelic drug of the amphetamine and MDxx families. It was first synthesized in the late 1990s by a team including David E. Nichols at Purdue University while investigating derivatives of 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxy-N-methylamphetamine (MDMA).

2,5-Dimethoxy-4-nitroamphetamine (DON) is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. Unlike related drugs like DOB, it produces both pronounced hallucinogenic and amphetamine-like stimulant effects. The drug is taken orally.

HOT-7, also known as '4-propylthio-2,5-dimethoxy-N-hydroxyphenethylamine or as N-hydroxy-2C-T-7', is a psychedelic drug of the phenethylamine, 2C, and HOT-x families. It is the N-hydroxy derivative of 2C-T-7. The drug is taken orally.