N-Methyltryptamine
N-Methyltryptamine, also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.
It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a known component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,''N-dimethyltryptamine and 5-methoxy-N'',N-dimethyltryptamine.
NMT acts as a serotonin receptor agonist and serotonin releasing agent and is said to produce hallucinogenic effects in humans.
NMT was encountered as a novel designer drug by 2014, though it is not commonly used itself due to its weak effects.
Use and effects
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.
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.In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent. It also releases dopamine and norepinephrine much more weakly.
NMT has also been evaluated for binding affinity at the sigma σ1 and sigma σ2 receptors. It's affinity towards both sigma receptors is intermediate between the unmethylated tryptamine and the fully dimethylated DMT.