N-Methyltryptamine

N-Methyltryptamine
Clinical data
Other names	NMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
Legal status
Legal status	US: Schedule I (isomer of AMT);
Identifiers
	IUPAC name 2-(1H-Indol-3-yl)-N-methylethan-1-amine;
CAS Number	61-49-4 ;
PubChem CID	6088;
ChemSpider	5863 ;
UNII	6FRL4L3Z7V;
KEGG	C06213 ;
ChEBI	CHEBI:28136 ;
ChEMBL	ChEMBL348588 ;
CompTox Dashboard (EPA)	DTXSID70209846 ;
ECHA InfoCard	100.000.462
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	87 to 89 °C (189 to 192 °F)
	SMILES CNCCc1c[nH]c2ccccc12;
	InChI InChI=1S/C11H14N2/c1-12-7-6-9-8-13-11-5-3-2-4-10(9)11/h2-5,8,12-13H,6-7H2,1H3 ; Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N ;
	(verify)

N-Methyltryptamine (NMT), 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.^[1]^[2] It is a known component in human urine.^[3] 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 (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).^[4]

NMT acts as a serotonin receptor agonist and serotonin releasing agent^[5] and is said to produce hallucinogenic effects in humans.^[6]^[7]^[8]

^ 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. PMID 15860375.
^ 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. PMID 16962229. S2CID 10272684.
^ 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. PMID 11763413. S2CID 218987277.
^ Ott, Jonathan (1996). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company. ISBN 978-0-9614234-8-3.
^ Cite error: The named reference BloughLandavazoDecker2014 was invoked but never defined (see the help page).
^ Cite error: The named reference TiHKAL1997 was invoked but never defined (see the help page).
^ Cite error: The named reference Nen2011 was invoked but never defined (see the help page).
^ Cite error: The named reference Nen2013 was invoked but never defined (see the help page).

[Renaissance_GPCR-1] 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. PMID 15860375.

[Burchett-2] 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. PMID 16962229. S2CID 10272684.

[pmid11763413-3] 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. PMID 11763413. S2CID 218987277.

[Ott1996-4] Ott, Jonathan (1996). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company. ISBN 978-0-9614234-8-3.

[BloughLandavazoDecker2014-5] Cite error: The named reference BloughLandavazoDecker2014 was invoked but never defined (see the help page).

[TiHKAL1997-6] Cite error: The named reference TiHKAL1997 was invoked but never defined (see the help page).

[Nen2011-7] Cite error: The named reference Nen2011 was invoked but never defined (see the help page).

[Nen2013-8] Cite error: The named reference Nen2013 was invoked but never defined (see the help page).

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