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5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT) is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL (“Tryptamines i Have Known And Loved”). It is claimed to show psychoactive effects at a dosage of 75-150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.

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.

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.

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