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N-Methyltryptamine

N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

Use and effects
Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. On the other hand, according to reports given to Alexander Shulgin and by others, NMT is active via non-oral routes. It has been said to produce psychedelic effects at doses of 50 to 120mg by smoking or vaporization, with a duration of seconds to minutes. Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects. NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI). ==Interactions==
Pharmacology
Pharmacodynamics NMT is known to act as a potent serotonin 5-HT2A receptor full agonist. It has been reported to be inactive in activating the β-arrestin2 pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor. The drug does not seem to be an agonist of the serotonin 5-HT1A receptor. Pharmacokinetics NMT undergoes oxidative deamination by monoamine oxidase (MAO), particularly MAO-A, which preferentially metabolizes serotonin and tryptamine derivatives. The intermediate methylation state of NMT makes it a substrate for further N-methylation to DMT by amine N-methyltransferase (INMT). ==Chemistry==
Chemistry
Synthesis The chemical synthesis of NMT has been described. Analogues Analogues of NMT include N-ethyltryptamine (NET), methylethyltryptamine (MET), and dimethyltryptamine (DMT), among others. ==Natural occurrence==
Natural occurrence
NMT is naturally occurring in Acacia species like Acacia confusa (1.63%; Buchanan et al., 2007), Acacia obtusifolia (up to two-thirds of total alkaloid content), and Acacia simplicifolia (A. simplex; 1.44% in bark, 0.29% twigs; Pouet et al., 1976) and Desmanthus illinoensis (major component seasonally). ==History==
History
NMT was encountered as a novel designer drug by 2014. ==Society and culture==
Society and culture
Legal status Canada NMT is not a controlled substance in Canada. United States In the United States, NMT is considered a schedule 1 controlled substance as an positional isomer of α-methyltryptamine (AMT). ==See also==
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