5-MeO-NMT

5-MeO-NMT, also known as 5-methoxy-N-methyltryptamine, is an tryptamine alkaloid, being the 5-methoxy analogue of N-methyltryptamine (NMT). It was first isolated from Phalaris arundinacea (reed canary grass) and also occurs in other species such as Virola species and Bufo alvarius skin. The compound has been synthesized by Alexander Shulgin and reported in his book TiHKAL (Tryptamines I Have Known and Loved).

Alexander Shulgin included 5-MeO-NMT as an entry in his book TiHKAL (Tryptamines I Have Known and Loved). However, he does not appear to have tried it and states that the dose and duration of the compound are unknown. In any case, Shulgin stated that it would be expected to be rapidly metabolized by monoamine oxidase and that it would likely only be active parenterally.

5-MeO-NMT is a potent agonist of the serotonin 5-HT_1A, 5-HT_2A, 5-HT_2B, and 5-HT_2C receptors. It is a full agonist or near-full agonist of all of these receptors except for the serotonin 5-HT_1A receptor, where it is a partial agonist. It additionally displays a high affinity for multiple other serotonin receptors. The drug is also a very weak serotonin releasing agent and has sub micromolar affinity for dopamine D₄ receptor.

5-MeO-NMT does not produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, and in some cases even reduced total HTRs. On the other hand, it does induce serotonin 5-HT_1A receptor-mediated hypothermia and hypolocomotion. Earlier reports had stated that 5-MeO-NMT and its N-demethylated analogue 5-methoxytryptamine were inactive, but this proved not to be the case.

The chemical synthesis of 5-MeO-NMT has been descibed.

Notable analogues of 5-MeO-NMT include NMT, 5-MeO-NET, 5-MeO-NiPT, norpsilocin (4-HO-NMT), baeocystin (4-PO-NMT), 4-HO-NALT, and 5-MeO-NBpBrT, among others. 5-MeO-NMT is the N-monodemethylated analogue of 5-MeO-DMT.

In the United States, this substance is a Schedule 1 analogue of bufotenin.^{[citation needed]}