Psychedelic tryptamines

Psilocybin, also known as '4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT'), is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Dimethyltryptamine (DMT), also known as '''N,N-dimethyltryptamine (N,N-DMT'''), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

Tryptamine, also known as 2-(3-indolyl)ethylamine, 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 first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time d

Bufotenin, also known as dimethylserotonin or as '5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT'), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitter serotonin (5-hydroxytryptamine; 5-HT). The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees Anadenanthera colubrina and Anadenanthera peregrina, has a long history of entheogenic use as a snuff in South America.

5-MeO-DMT, also known as '5-methoxy-N,N-dimethyltryptamine, as well as O-methylbufotenin or mebufotenin', is an atypical psychedelic drug, entheogen, and alkaloid of the tryptamine and 5-methoxytryptamine families. It is found naturally in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad (Incilius alvarius, formerly Bufo alvarius). It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

TiHKAL: The Continuation, also known as Tryptamines I Have Known and Loved, is a 1997 book written by Alexander Shulgin and Ann Shulgin. It is about a family of psychoactive drugs known as tryptamines, which includes psychedelics, other hallucinogens, and entactogens. The book has two halves, and the second part of the book contains detailed entries on 55tryptamines. TiHKAL is a sequel to PiHKAL: A Chemical Love Story (Phenethylamines I Have Known and Loved) (1991).

'''N-Methyltryptamine (NMT), also known as monomethyltryptamine''', is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

Diethyltryptamine (DET), also known as '''N,N-diethyltryptamine or T-9''', is a psychedelic drug of the tryptamine family closely related to dimethyltryptamine (DMT). It is taken orally, but can also be used by parenteral routes.

Dipropyltryptamine (DPT), also known as '''N,N-dipropyltryptamine or as "The Light'''", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is taken orally or by other routes.

Baeocystin, also known as norpsilocybin or '4-phosphoryloxy-N-methyltryptamine (4-PO-NMT'), is a zwitterionic alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms together with psilocybin, psilocin (4-HO-DMT), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT). The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).

Diisopropyltryptamine (DiPT), also known as '''N,N-diisopropyltryptamine''', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is unusual among psychedelics in that at usual doses it primarily or exclusively produces strong auditory changes, including decreased pitch, harmonic distortion, and sound unfamiliarity, but produces no other hallucinogenic effects such as visuals. However, the drug may produce more classically psychedelic effects at very high doses. It is taken orally, but can also be smoked.

5-MeO-DiPT, also known as '5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and distinct effects from other serotonergic tryptamines, including some stimulant- and entactogen-like effects, robust tactile and sexual enhancement, and only light hallucinogenic effects. The drug is usually taken orally, but may also be used by other routes.

Norbaeocystin, also known as 4-phosphoryloxytryptamine (4-PO-T), is a psilocybin mushroom alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms, together with psilocybin, psilocin (4-HO-DMT), aeruginascin (4-PO-TMT), and baeocystin (4-PO-NMT), from which it is a derivative.

4-HO-DiPT, also known as '4-hydroxy-N,N-diisopropyltryptamine or as iprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally. The drug has an unusually fast onset, short duration, and narrow dose range. Among orally administered psychedelics, it is one of the shortest-acting compounds known.

4-HO-MET, also known as '4-hydroxy-N-methyl-N-ethyltryptamine, as well as metocin or methylcybin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.

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

4-AcO-DiPT, also known as '4-acetoxy-N,N-diisopropyltryptamine or as ipracetin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to 4-AcO-DMT (psilacetin). It is taken orally.

5-MeS-DMT, also known as '5-methylthio-N,N-dimethyltryptamine or as 5-methylthio-DMT', is a lesser-known psychedelic drug of the tryptamine family. It is the 5-methylthio derivative of dimethyltryptamine (DMT) and is an analogue of 5-MeO-DMT.

Methylisopropyltryptamine (MiPT), also known as '''N-methyl-N-isopropyltryptamine''', is a psychedelic drug of the tryptamine family related to other psychedelics like dimethyltryptamine (DMT) and diisopropyltryptamine (DiPT). It is taken orally.

5-Methoxytryptamine (5-MT, 5-MeO-T, or 5-OMe-T), also known as serotonin methyl ether or '''O-methylserotonin and as mexamine', is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the pineal gland of the brain. It is formed via O-methylation of serotonin or N''-deacetylation of melatonin.

5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as 'α,O-dimethylserotonin (α,O-DMS or Alpha-O'), is a psychedelic drug of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT. The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines). It is taken orally and is used at doses of 2 to 4mg.

4-MeO-MiPT, also known as '4-methoxy-N-methyl-N-isopropyltryptamine', is a lesser-known psychedelic drug of the tryptamine and 4-methoxytryptamine families. It is the 4-methoxy analogue of MiPT and the O-methyl ether of 4-HO-MiPT. The drug is taken orally.

Methylethyltryptamine (MET), also known as '''N-methyl-N-ethyltryptamine (N,N-MET'''), is a psychedelic drug of the tryptamine family. It is taken orally or via inhalation.

4-HO-MiPT, also known as '4-hydroxy-N-methyl-N-isopropyltryptamine or as miprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It appears to be similar to psilocin in terms of onset, duration, and effects. The drug is taken orally.

5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

2-Me-DET, or 2-methyl-DET, also known as '2-methyl-N,N-diethyltryptamine', is a psychedelic drug of the tryptamine family. It is the 2-methyl derivative of diethyltryptamine (DET). The drug is taken orally.

4-AcO-MiPT, also known as '4-acetoxy-N-methyl-N-isopropyltryptamine or as mipracetin', is a psychedelic tryptamine. It is closely related to 4-AcO-DMT and methylisopropyltryptamine (MiPT).

5-MeO-MiPT, also known as '5-methoxy-N-methyl-N-isopropyltryptamine or by its nickname Moxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and unusual effects compared to other psychedelic tryptamines. At low doses, its effects include stimulation, tactile and sexual enhancement, some MDMA-like entactogenic effects, and introspective and mild perceptual changes with few or no psychedelic visuals or time dilation, whereas at higher doses, it produces 5-MeO-DMT-like classical psychedelic effects. It is usually taken orally or smoked.

5-MeO-pyr-T, also known as '5-methoxy-N,N-tetramethylenetryptamine or as 5-methoxy-3-(2-pyrrolidinoethyl)indole', is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and pyrrolidinylethylindole families. It is the 5-methoxy analogue of pyr-T and the derivative of 5-MeO-DMT and 5-MeO-DET in which their N,N-dialkyl groups have been cyclized into a pyrrolidine ring.

5-MeO-DALT, also known as '''N,N-diallyl-5-methoxytryptamine or as foxtrot''', is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. It is taken orally.

4-Me-αMT (developmental code name MP-809), or 4-Me-AMT, also known as 4-methyl-α-methyltryptamine or as 4,α-dimethyltryptamine (4,α-DMT), is an experimental antidepressant of the tryptamine and α-alkyltryptamine families that was never marketed. It is closely structurally related to serotonergic psychedelics and entactogens like α-methyltryptamine (αMT) and α-ethyltryptamine (αET).

4-AcO-DALT, also known as '4-acetoxy-N,N-diallyltryptamine or as dalcetin', is a tryptamine derivative. It has been sold as a designer drug, but little other information is available. It was first officially identified in seized drug samples in 2012.

Dibutyltryptamine (DBT), also known as '''N,N-dibutyltryptamine (N,N-DBT'''), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).

5-MeO-DET, also known as '5-methoxy-N,N-diethyltryptamine' is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. It is taken orally but can also be used parenterally.

Ethocybin also known as '4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin. It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

4-HO-DET, also known as '4-hydroxy-N,N-diethyltryptamine as well as ethocin or CZ-74', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

'5,N,N-Trimethyltryptamine (5,N,N-TMT; 5-TMT), also known as 5-methyl-DMT', is a tryptamine derivative that may be a psychedelic drug. It was first made in 1958 by Edwin H. P. Young. In animal experiments it was found to be in between DMT and 5-MeO-DMT in potency.

4-HO-DBT, also known as '4-hydroxy-N,N-dibutyltryptamine', is a psychedelic drug of the tryptamine family related to psilocin (4-HO-DMT). It is taken orally.

Aeruginascin, also known as '4-phosphoryloxy-N,N,N-trimethyltryptamine (4-PO-TMT'), is an indoleamine derivative which occurs naturally within the mushrooms Inocybe aeruginascens, Pholiotina cyanopus, and Psilocybe cubensis. It was discovered by Jochen Gartz.

'7,N,N-trimethyltryptamine (7,N,N-TMT or 7-TMT), also known as 7-methyl-DMT', is a serotonin receptor modulator and psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It was first described by 1978 and was encountered online as a novel designer drug in 2024.

5-Fluoro-DMT, or 5-F-DMT, also known as '5-fluoro-N,N-dimethyltryptamine', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) and to other psychedelic tryptamines like 5-chloro-DMT and 5-bromo-DMT.

5-HO-DiPT, also known as '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 been encountered as a designer drug in its own right. Tests in vitro show 5-HO-DiPT to have high serotonin 5-HT2A receptor affinity and good selectivity over the serotonin 5-HT1A receptor, while being more lipophilic than the related drug bufotenine (5-HO-DMT), which produces primarily peripheral effects.

4-MeO-DMT, or 4-methoxy-DMT, also known as '4-methoxy-N,N-dimethyltryptamine or as O-methylpsilocin (PSOM'), is a serotonin receptor modulator and possible psychedelic drug of the tryptamine and 4-hydroxytryptamine families. It is the O-methylated analogue of psilocin (4-HO-DMT) and a positional isomer of 5-MeO-DMT.

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or as 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.

4-HO-DPT, also known as '4-hydroxy-N,N-dipropyltryptamine or as deprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

Diallyltryptamine (DALT), also known as '''N,N-diallyltryptamine''', is a tryptamine derivative which has been identified as a designer drug.