N-Methyltryptamine (NMT), also known asmonomethyltryptamine, is achemical compound of thetryptamine family and anaturally occurring compound found in the human body and certain plants.
According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.[11] On the other hand, according to reports given toAlexander Shulgin and by others, NMT is active vianon-oralroutes.[1][2][3] It has been said to producepsychedelic effects at doses of 50 to 120mg bysmoking orvaporization, with aduration of seconds to minutes.[1][2][3] Based on preliminary reports, NMT is reported to producevisuals, but its effects are described as primarilyspatial in nature, among other effects.[1][2][3]
In addition to its serotonin 5-HT2A receptor agonism, NMT is a potentserotonin releasing agent.[8] It also releasesdopamine andnorepinephrine much more weakly (14- and 33-fold less than for serotonin, respectively).[8]
NMT undergoes oxidativedeamination bymonoamine oxidase (MAO), particularlyMAO-A, which preferentially metabolizes serotonin and tryptamine derivatives. The intermediate methylation state of NMT makes it a substrate for further N-methylation to DMT byamineN-methyltransferase (INMT).
^abcdefghShulgin A, Shulgin A (1997).TiHKAL: The Continuation. Berkeley: Transform Press.To my knowledge there have been no reports of oral activity of NMT, although its wide availability from botanic sources has encouraged some explorers to assay it. I have had one report that the smoking of 50–100 mg gave visuals that lasted for maybe 15 seconds.
^Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family".Trends in Pharmacological Sciences.26 (5):274–281.doi:10.1016/j.tips.2005.03.007.PMID15860375.
^Burchett SA, Hicks TP (August 2006). "The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain".Progress in Neurobiology.79 (5–6):223–246.doi:10.1016/j.pneurobio.2006.07.003.PMID16962229.S2CID10272684.
^Forsström T, Tuominen J, Karkkäinen J (2001). "Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS".Scandinavian Journal of Clinical and Laboratory Investigation.61 (7):547–56.doi:10.1080/003655101753218319.PMID11763413.S2CID218987277.
^Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144.ISBN978-0-85608-011-1.OCLC2176880.OL4850660M.N-Monoalkyltryptamines resemble the unsubstituted tryptamines in being good substrates for amine oxidases (Erspamer, 1955), a property which is reflected in their relatively poor hallucinogenic activity as compared to their N,N-dialkyl analogues. Thus, neither tryptamine nor its N-methyl derivative, both of which are oxidatively deaminated in rats to free (and conjugated) indole-3-acetic acids to the extent of 84·6 and 35·7 per cent respectively, produce behavioural changes in animals or man, whereas N,N-dimethyltryptamine, which is but little affected by amine oxidases, is a potent hallucinogen.
