N-Methyltryptamine

N-Methyltryptamine
Identifiers
	show IUPAC name
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)
	show SMILES
	show InChI
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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.^[1]^[2] It is a common 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).^{[citation needed]}

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism.^[4] However, it may become active upon combination with a MAO_A inhibitor (MAOI).^[4] 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.^[5]^[6]

References[]

^ Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends Pharmacol. Sci. 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". Prog. Neurobiol. 79 (5–6): 223–46. doi:10.1016/j.pneurobio.2006.07.003. PMID 16962229. S2CID 10272684.
^ Scand J Clin Lab Invest. 2001;61(7):547-56. Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Forsström T, Tuominen J, Karkkäinen J.
^ Jump up to: ^a ^b Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams
^ Shulgin & Shulgin "TIKHAL" 1997
^ Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.

External links[]

[Renaissance_GPCR-1] Lindemann L, Hoener MC (May 2005). "A renaissance in trace amines inspired by a novel GPCR family". Trends Pharmacol. Sci. 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". Prog. Neurobiol. 79 (5–6): 223–46. doi:10.1016/j.pneurobio.2006.07.003. PMID 16962229. S2CID 10272684.

[3] Scand J Clin Lab Invest. 2001;61(7):547-56. Determination of potentially hallucinogenic N-dimethylated indoleamines in human urine by HPLC/ESI-MS-MS. Forsström T, Tuominen J, Karkkäinen J.

[ReferenceA-4] Jump up to: ^a ^b Foye's principles of medicinal chemistry By William O. Foye, Thomas L. Lemke, David A. Williams

[5] Shulgin & Shulgin "TIKHAL" 1997

[6] Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.

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Identifiers

show IUPAC name 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number	61-49-4^N
PubChem CID	6088
ChemSpider	5863^Y
UNII	6FRL4L3Z7V
KEGG	C06213^Y
ChEBI	CHEBI:28136^Y
ChEMBL	ChEMBL348588^Y
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)
show SMILES CNCCc1c[nH]c2ccccc12
show 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^Y Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N^Y
^NY (what is this?)

N-Methyltryptamine

See also[]

References[]

External links[]