Chemistry:N-Methyltryptamine

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Short description: Chemical compound


N-Methyltryptamine
NMT structure.svg
Legal status
Legal status
  • US: Schedule I (isomer of AMT)
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC11H14N2
Molar mass174.247 g·mol−1
3D model (JSmol)
Melting point87 to 89 °C (189 to 192 °F)
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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 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. ↑ "A renaissance in trace amines inspired by a novel GPCR family". Trends in Pharmacological Sciences 26 (5): 274–281. May 2005. doi:10.1016/j.tips.2005.03.007. PMID 15860375. 
  2. ↑ "The mysterious trace amines: protean neuromodulators of synaptic transmission in mammalian brain". Progress in Neurobiology 79 (5–6): 223–246. August 2006. doi:10.1016/j.pneurobio.2006.07.003. PMID 16962229. 
  3. ↑ "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. 2001. doi:10.1080/003655101753218319. PMID 11763413. 
  4. ↑ 4.0 4.1 "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). 2002. p. 439. ISBN 9780683307375. https://books.google.com/books?id=qLJ6Bs1Qml4C&q=NMT&pg=PA439. 
  5. ↑ TIKHAL. Berkeley: Transform Press. 1997. 
  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". August 2023. https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf. 

External links



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