PiHKAL

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

Mescaline, also known as mescalin or mezcalin, and in chemical terms 3,4,5-trimethoxyphenethylamine, is a naturally occurring classical psychedelic protoalkaloid of the substituted phenethylamine class, found in cacti like peyote (Lophophora williamsii) and San Pedro (certain species of the genus Echinopsis).

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 amine-associated receptor 1 (TAAR1) and inhibiting vesicular monoamine transporter 2 (VMAT2) in monoamine neurons. To a lesser extent, it also acts as a neurotransmitter in the human central nervous system. In mammals, phenethylamine is produced from the amino acid L-phenylalanine by the enzyme aromatic L-amino acid decarboxylase via enzymatic decarboxylation.

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.

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.

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

'3,4-Methylenedioxy-N-ethylamphetamine (MDEA; also called MDE and colloquially, Eve') is an empathogenic psychoactive drug. MDEA is a substituted amphetamine and a substituted methylenedioxyphenethylamine. MDEA acts as a serotonin, norepinephrine, and dopamine releasing agent and reuptake inhibitor.

'''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.

2,5-Dimethoxy-4-bromoamphetamine (DOB), also known as brolamfetamine (), is a psychedelic drug of the phenethylamine, amphetamine, and DOx families. For many years, prior to the discovery of newer compounds, DOB was the most potent known phenethylamine psychedelic. It 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.

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.

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.

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

MBDB, also known as '''N-methyl-1,3-benzodioxolylbutanamine or as 3,4-methylenedioxy-N-methyl-α-ethylphenylethylamine, is an entactogen of the phenethylamine, amphetamine, and phenylisobutylamine families related to MDMA. It is known by the nicknames "Eden" and "Methyl-J'''".

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.

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.

'''para-Methoxymethamphetamine (PMMA), also known as 4-methoxy-N-methylamphetamine (4-MMA'), is a serotonergic drug of the amphetamine family related to para''-methoxyamphetamine (PMA). It is the 4-methoxy analogue of methamphetamine.

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-H, also known as 2,5-dimethoxyphenethylamine (2,5-DMPEA) or as DMPEA-4, is a chemical compound of the phenethylamine and 2C families. It is the parent compound of the 2C drugs, which are also known as 4-substituted 2,5-dimethoxyphenethylamines.

group of stereoisomers

chemical compound

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.

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).

Buscaline (B), also known as 4-butoxy-3,5-dimethoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline. It is the derivative of mescaline in which the methoxy group at the 4 position has been replaced with a butoxy group.

chemical compound

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).

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.

'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).

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).

chemical compound

Trisescaline (TRIS), also known as trescaline or as 3,4,5-triethoxyphenethylamine, is a chemical compound of the phenethylamine and scaline families related to mescaline. It is the derivative of mescaline in which the three methoxy groups on the phenyl ring have been replaced with ethoxy groups.

MDBU, also known as '3,4-methylenedioxy-N-butylamphetamine or as N-butyl-MDA', is a lesser-known drug. It is the N-butyl derivative of 3,4-methylenedioxyamphetamine (MDA).

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

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.

MDIP, also known as '3,4-methylenedioxy-N-isopropylamphetamine or as N-isopropyl-MDA', is a psychoactive drug of the phenethylamine and amphetamine families. It is the N-isopropyl analogue of 3,4-methylenedioxyamphetamine (MDA).

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

chemical compound

Methyl-DOB, or '''N-methyl-DOB, also known as 4-bromo-2,5-dimethoxy-N-methylamphetamine, MDOB, or M-154', is a psychoactive drug of the phenethylamine, amphetamine, and DOx families. It is the N''-methyl derivative of the psychedelic drug DOB.

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.

psychoactive chemical compound

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-T-21, also known as 4-(2-fluoroethylthio)-2,5-dimethoxyphenethylamine, is a psychedelic phenethylamine of the 2C family. It is taken orally.

Isomescaline (IM), also known as 2,3,4-trimethoxyphenethylamine (2,3,4-TMPEA) or as TMPEA-3 or 2C-TMA-3, is a chemical compound of the phenethylamine and scaline families related to the psychedelic drug mescaline (3,4,5-trimethoxyphenethylamine; 2,3,4-TMPEA). It is one of several possible positional isomers of trimethoxyphenethylamine (TMPEA). In addition, it is the positional isomer of mescaline in which the methoxy groups on the phenyl ring are located at the 2, 3, and 4 positions instead of at the 3, 4, and 5 positions.

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.

MDPH, also known as 3,4-methylenedioxyphentermine or as α-methyl-MDA, is a psychoactive drug of the amphetamine family. MDPH was first synthesized by Alexander Shulgin. Very little data exists about the pharmacological properties, metabolism, and toxicity of MDPH.

2C-O-4, also known as 4-isopropoxy-2,5-dimethoxyphenethylamine, is a phenethylamine of the 2C family. It is also a positional isomer of isoproscaline and was probably first synthesized by Alexander Shulgin. It produces hallucinogenic or psychedelic effects. Because of the low potency of 2C-O-4, and the inactivity of 2C-O, Shulgin felt that the 2C-O series would not be an exciting area for research, and did not pursue any further analogues.

chemical compound

'3,4-Methylenedioxy-N,N-dimethylamphetamine (MDDM, MDDMA), also known as N,N-dimethyl-MDA or N-methyl-MDMA', is a lesser-known serotonin releasing agent and psychoactive drug of the phenethylamine, amphetamine, and MDxx families. It is the N,N-dimethyl analogue of 3,4-methylenedioxyamphetamine (MDA) and the N-methyl derivative of MDMA. The drug is a known synthetic impurity of MDMA and has also been described as a possible novel designer drug in 2025.

Phenescaline, also known as 3,5-dimethoxy-4-phenylethoxyphenethylamine, is a psychoactive drug of the phenethylamine and scaline families related to mescaline. It is the derivative of mescaline in which the methoxy group at the 4 position has been replaced with a phenylethoxy group. In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists phenescaline's dose as greater than 150mg orally and its duration as unknown. The effects of phenescaline have been reported to include threshold effects and a vague unreal feeling as if one had not had enough sleep. The drug shows

2C-T-15, also known as 4-cyclopropylthio-2,5-dimethoxyphenethylamine or as Sesqui, is a psychoactive drug of the phenethylamine and 2C families.

MEDA, also known as 3-methoxy-4,5-ethylenedioxyamphetamine or as 5-methoxy-EDA, is a chemical compound of the phenethylamine, amphetamine, and EDxx families. It is the EDxx analogue of the MDxx psychedelic and entactogen MMDA (5-methoxy-MDA). In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists MEDA's dose as greater than 200mg orally and its duration as unknown. MEDA produced few to no effects at tested doses. The chemical synthesis of MEDA has been described. MEDA was first described in the scientific literature by Shulgin in 1964. Subsequently, it was describ

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.