Formula C10H12N2 | Molar mass 160.2157 g/mol | |
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Appearance white to orange crystalline powder | ||
Tryptamine
Tryptamine is a monoamine alkaloid. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which the name derives. Tryptamine is found in trace amounts in the brains of mammals and is hypothesized to play a role as a neuromodulator or neurotransmitter. Similar to other trace amines, tryptamine binds to human trace amine-associated receptor 1 (TAAR1) as an agonist.
Contents
Tryptamine is the common functional group in a set of compounds termed collectively substituted tryptamines. This set includes many biologically active compounds, including neurotransmitters and psychedelic drugs.
The concentration of tryptamine in rat brains is about 3.5 pmol/g.
Plants containing tryptamine
Many plants contain small amounts of tryptamine. It is a feedstock for the metabolic pathways which influence plant growth and microbiome. For example, it is found as a possible intermediate in one biosynthetic pathway to the plant hormone indole-3-acetic acid. Higher concentrations can be found in many Acacia species.
Pharmacology
Tryptamine is an agonist of hTAAR1. It acts as a non-selective serotonin receptor agonist and serotonin-norepinephrine-dopamine releasing agent (SNDRA), with a preference for evoking serotonin and dopamine release over norepinephrine release.
Tryptamine has been shown to act as a noncompetitive inhibitor of serotonin N-acetyltransferase (SNAT) in mosquitoes. SNAT catalyzes the anabolic metabolism of serotonin into N-acetylserotonin, another neuromodulator (specifically a neurotrophic factor via TrkB agonism) and the immediate precursor for melatonin.
Tryptamine is rapidly metabolized by MAO-A and MAO-B, and for this reason, has a very short in vivo half-life.
Synthesis
The Abramovitch–Shapiro tryptamine synthesis is an organic reaction for the synthesis of tryptamine.