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
Legal status
Legal status
Identifiers
  • 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)
  • CNCCc1c[nH]c2ccccc12
  • 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 checkY
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N checkY
 ☒NcheckY (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]

Legality

In the United States N-Methyltryptamine is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT) [7]

See also

References
  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.
  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.
  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.
  4. Foye WO, Lemke TL, Williams DA (2002). "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). p. 439. ISBN 9780683307375.
  5. Shulgin A, Shulgin A (1997). TIKHAL. Berkeley: Transform Press.
  6. Nen - lecture presented EGA conference, Victoria, Australia 4/12/2011; and Breaking Conventions, London 12/7/2013.
  7. "Orange Book - List of Controlled Substances and Regulated Chemicals" (PDF). U.S. Department of Justice Diversion Control Division. August 2023. Archived (PDF) from the original on September 6, 2023.
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