N-Methyltryptamine

N-Methyltryptamine
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 ;
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N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common 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 (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. However, it may become active upon combination with a MAO_A inhibitor (MAOI). By vaporization NMT shows activity at 50–100 mg, with a duration of 45–70 minutes; duration of visual effects 15–30 seconds. Effects are primarily non-visual.

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