Tryptamine

Tryptamine is an indole-based organic compound with an ethylamine side chain. It occurs naturally in plants and animals and forms the structural basis of many biologically active compounds.

Indole: An aromatic heterocyclic compound formed by a benzene ring fused to a pyrrole ring. Tryptamine consists of this fused-ring scaffold attached to an ethylamine side chain.
Tryptophan decarboxylase: An enzyme that removes the carboxyl group from tryptophan to produce tryptamine. It catalyzes the principal biosynthetic step from tryptophan to tryptamine.
Melatonin: A hormone derived from serotonin that helps regulate circadian rhythms and sleep timing. Its synthesis proceeds through serotonin, linking melatonin to the tryptamine scaffold.
Phenethylamine: An aromatic amine consisting of a phenyl ring attached to an ethylamine side chain. It shares tryptamine’s two-carbon amine chain but lacks the fused indole ring.
Ethylamine: A primary amine with a two-carbon chain, represented by the formula C₂H₇N. Tryptamine’s side chain contains two carbon atoms and ends in an amine group.
Tryptophan: An essential amino acid used in protein synthesis and as a precursor to several bioactive molecules. Decarboxylation of tryptophan produces tryptamine.
Psilocybin: A naturally occurring psychedelic prodrug that is converted in the body to psilocin. Psilocybin is a phosphorylated tryptamine derivative found in certain fungi.
Tyramine: A biogenic amine produced by decarboxylating the amino acid tyrosine. Tyramine is another amino-acid-derived amine, but its aromatic scaffold is a substituted phenyl ring.
Aromaticity: The stabilization associated with cyclic, conjugated electron systems that satisfy aromatic electron-counting rules. Aromaticity helps explain the stability and characteristic reactions of tryptamine’s indole ring.
Monoamine oxidase: An enzyme family that oxidatively deaminates monoamine neurotransmitters and related compounds. Monoamine oxidases help break down tryptamine and related amines.

Linked from 3 pages

PsilocinNarrower topic: Psilocin belongs to this chemical family, whose members include serotonin and other psychedelics.