Tryptamine
Tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine in turn acting as a precursor for other compounds including indole and beta-carboline alkaloids and auxins.
Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animals are commonly used by humans for their psychoactive effects, which tend to be psychedelic in nature. Prominent examples include psilocybin (from "magic mushrooms") and DMT (from numerous plant sources, e.g. ayahuasca). Many synthetic tryptamines have also been made. The table below lists some commonly encountered substituted tryptamines.
The tryptamine backbone can also be identified as part of the structure of some more complex compounds, for example: ergot alkaloids, LSD, ibogaine and yohimbinine.
A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.
| Short Name | α | R4 | R5 | N1 | N2 | Full Name |
|---|---|---|---|---|---|---|
| serotonin | OH | 5-hydroxytryptamine | ||||
| melatonin | OCH3 | O=CH-CH3 | 5-methoxy-N-acetyltryptamine | |||
| DMT | CH3 | CH3 | N,N-dimethyltryptamine | |||
| DET | CH2CH3 | CH2CH3 | N,N-diethyltryptamine | |||
| DPT | CH2CH2CH3 | CH2CH2CH3 | N,N-dipropyltryptamine | |||
| bufotenine | OH | CH3 | CH3 | 5-hydroxy-N,N-dimethyltryptamine | ||
| 5-MeO-DMT | OCH3 | CH3 | CH3 | 5-methoxy-N,N-dimethyltryptamine | ||
| psilocin | OH | CH3 | CH3 | 4-hydroxy-N,N-dimethyltryptamine | ||
| psilocybin | OPO3H2 | CH3 | CH3 | 4-phosphoryloxy-N,N-dimethyltryptamine | ||
| AMT | CH3 | α-methyltryptamine |