N-Methyltryptamine

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).

N-Methyltryptamine
Identifiers
IUPAC name
  • 2-(1H-Indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.462
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
Melting point87 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 Y
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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 MAOA 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]

See also
  • N-Ethyltryptamine (NET)
  • N,N,-Dimethyltryptamine (DMT)
  • Acacia confusa (a natural source of NMT, with other tryptamines, 1.63%. Buchanan et al. 2007)
  • Acacia obtusifolia (NMT up to 2/3 alkaloid content)
  • Acacia simplicifolia (synon. A. simplex) (1.44% NMT in bark, 0.29% twigs, Pouet et al. 1976)
  • Desmanthus illinoensis (NMT major component seasonally)

References
  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.
  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.
  4. 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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