Tryptamines

An indole with an ethylamine side chain, grouped by where the ring is substituted: the 4-position compounds (psilocybin and its active form psilocin, 4-AcO-DMT, 4-HO-MET, 4-HO-MiPT), the 5-methoxy compounds (5-MeO-DMT, 5-MeO-MiPT, bufotenin), and the α-alkyl tryptamines (AMT, AET, 5-MeO-AMT), which behave like a different class — they release monoamines, inhibit MAO, and last far longer. Serotonin, melatonin and tryptamine itself are filed here as the endogenous reference points.

Route decides more here than anywhere else in the subject. DMT is inactive swallowed unless MAO is inhibited, which is what the β-carbolines are for, and the 4-acetoxy and 4-phosphoryloxy compounds are prodrugs for the 4-hydroxy ones. Amanita muscaria is not here — there is no tryptamine in it; muscimol is filed under Atypical. The α-alkyl members combined with any other serotonergic drug are this family's serotonin-syndrome risk.