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, beta-carboline and ergoline 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, including the migraine drug sumatriptan and its relatives. 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: ergoline alkaloids, LSD, ibogaine and yohimbine.

A thorough investigation of dozens of tryptamine compounds was published by Ann and Alexander Shulgin under the title TiHKAL.

Substituted tryptamines, tabulated by structure

Short Name	α	R4	R5	N1	N2	Full Name
serotonin			OH			5-hydroxytryptamine
melatonin			OCH3	O=CH-CH3		5-methoxy-N-acetyltryptamine
sumatriptan		SO2NHCH3		CH3	CH3	4-methylaminosulfonyl-N,N-dimethyltryptamine
DMT				CH3	CH3	N,N-dimethyltryptamine
DET				CH2CH3	CH2CH3	N,N-diethyltryptamine
DPT				CH2CH2CH3	CH2CH2CH3	N,N-dipropyltryptamine
DiPT				CH3CH3C	CH3CH3C	N,N-diisopropyltryptamine
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
5-MeO-AMT	CH3		OCH3			5-methoxy-α-methyltryptamine

See also

• TiHKAL
• Indoles
• Beta-carbolines
• Ergolines
• 5-MeO-DIPT

• Tryptamine FAQ