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. 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.
5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin, is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. 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-methoxy, the power, bufo, and toad venom.
5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.
A serotonin receptor agonist is an agonist of one or more serotonin receptors. They activate serotonin receptors in a manner similar to that of serotonin, a neurotransmitter and hormone and the endogenous ligand of the serotonin receptors.
5-Methoxytryptamine, 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 body in low levels, especially in the pineal gland. It is formed via O-methylation of serotonin or N-deacetylation of melatonin.
α,N-Dimethyltryptamine (α,N-DMT; developmental code names SK&F-7024, Ro 3-1715), also known as N-methyl-α-methyltryptamine (N-methyl-αMT), is a lesser-known substituted tryptamine and psychoactive drug. It is the α,N-dimethyl positional isomer of N,N-dimethyltryptamine (N,N-DMT).
5-Fluoro-α-methyltryptamine, also known as PAL-212 or PAL-544, is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT).
A serotonin–dopamine releasing agent (SDRA) is a type of drug which induces the release of serotonin and dopamine in the body and/or brain.
Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine analogues), are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known serotonin–dopamine releasing agents (SDRAs). It is also a potent serotonin 5-HT2A receptor agonist and hence may be a serotonergic psychedelic. The drug has been investigated in animals as a potential treatment for cocaine dependence.
5-Fluoro-AET, also known as 5-fluoro-α-ethyltryptamine or by the code name PAL-545, is a substituted tryptamine derivative which acts as a serotonin–dopamine releasing agent (SDRA) and as an agonist of the serotonin 5-HT2A receptor.
BK-NM-AMT, or βk-NM-αMT, also known as β-keto-N-methyl-αMT or α,N-dimethyl-β-ketotryptamine, as well as 3-indoylmethcathinone, is a serotonin–dopamine releasing agent (SDRA) and putative entactogen of the tryptamine, α-alkyltryptamine, and β-ketotryptamine families. Along with certain other tryptamines, such as α-ethyltryptamine (αET), 5-chloro-αMT and 5-fluoro-αET, it is one of the few SDRAs known.
α-Methylisotryptamine is a synthetic compound belonging to the tryptamine class, known for its psychoactive properties. As a structural analog of α-methyltryptamine (αMT), isoAMT exhibits entactogenic and psychedelic effects.
isoDMT, also known as N,N-dimethylisotryptamine, is a putatively non-hallucinogenic serotonin 5-HT2A receptor agonist and psychoplastogen of the isotryptamine group. It is the isotryptamine homologue of dimethyltryptamine (DMT), a more well-known serotonergic psychedelic of the tryptamine family, and represents a small structural modification of DMT.
5-Chloro-αET, or 5-chloro-AET, also known as 5-chloro-α-ethyltryptamine, is a serotonergic agent of the tryptamine and α-alkyltryptamine families. It is the derivative of α-ethyltryptamine with a 5-chloro substitution. Analogues of 5-chloro-αET include 5-fluoro-αET, 5-chloro-αMT, and 5-fluoro-αMT.
1ZP2MA, also known as [1-(indolizin-1-yl)propan-2-yl](methyl)amine or as 1-(indolizin-1-yl)-N-methylpropan-2-amine, is a monoamine releasing agent and an indolizine derivative. It is the analogue and positional isomer of the stimulant-like drug α,N-dimethyltryptamine (α,N-DMT or N-methyl-α-methyltryptamine (N-methyl-αMT)) in which the indole ring has been replaced with an indolizine ring. 1ZP2MA has been found to be a potent dopamine releasing agent, with an EC50 of 62 nM. It is the α-methyl and N-desmethyl analogue of (2-(indolizin-1-yl)ethyl)dimethylamine (TACT908; the indolizine analogue of dimethyltryptamine (DMT)). 1ZP2MA and 2ZEDMA were patented by Tactogen in 2023.
1Z2MAP1O, also known as 1-(indolizin-3-yl)-2-(methylamino)propan-1-one, is a monoamine releasing agent and serotonin receptor modulator and an indolizine derivative. It is an analogue of BK-NM-AMT (β-keto-N-methyl-α-methyltryptamine) in which the indole ring has been replaced with an indolizine ring.
3-APBT, also known as 3-(2-aminopropyl)benzo[β]thiophene, is a monoamine releasing agent and serotonin receptor agonist of the benzothiophene group. It is an analogue of α-methyltryptamine (AMT) in which the indole ring has been replaced with a benzothiophene ring.
3-APB, also known as 3-(2-aminopropyl)benzofuran, is a drug of the benzofuran family related to α-methyltryptamine (AMT). It is an analogue of AMT in which the indole ring has been replaced with a benzofuran ring.
