N-Methyltryptamine

Last updated
N-Methyltryptamine
NMT structure.svg
Clinical data
Other namesNMT; Methyltryptamine; N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
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 InfoCard 100.000.462 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H14N2
Molar mass 174.247 g·mol−1
3D model (JSmol)
Melting point 87 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 Yes check.svgY
  • Key:NCIKQJBVUNUXLW-UHFFFAOYSA-N Yes check.svgY
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N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.

Contents

It is biosynthesized in humans from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. [1] [2] It is a known 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). [4]

NMT acts as a serotonin receptor agonist and serotonin releasing agent [5] and is said to produce hallucinogenic effects in humans. [6] [7] [8]

Effects

Orally administered NMT appears to produce no psychoactive effects, likely as a result of extensive first-pass metabolism. [9]

Per Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided. [10] On the other hand, according to Alexander Shulgin and others, NMT is active via non-oral routes. [6] [7] [8] It has been said to produce psychedelic effects at doses of 50 to 120 mg by smoking or vaporization, with a duration of seconds to minutes. [6] [7] [8] Based on preliminary reports, NMT is reported to produce visuals, but its effects are described as primarily spatial in nature, among other effects. [6] [7] [8]

NMT has also been reported to be orally active in combination with a monoamine oxidase inhibitor (MAOI). [7] [8]

Pharmacology

NMT is known to act as a potent serotonin 5-HT2A receptor full agonist (EC50 Tooltip half-maximal effective concentration = 50.7 nM; Emax Tooltip maximal efficacy = 96%). [5] It has been reported to be inactive in activating the β-arrestin pathway of the receptor and hence appears to be a biased agonist of the serotonin 5-HT2A receptor. [5] The drug is not an agonist of the serotonin 5-HT1A receptor. [5]

In addition to its serotonin 5-HT2A receptor agonism, NMT is a potent serotonin releasing agent (EC50 = 22.4 nM). [5] It also releases dopamine and norepinephrine much more weakly (EC50 = 321 nM and 733 nM, respectively; 14- and 33-fold less than for serotonin, respectively). [5]

Society and culture

In the United States NMT is considered a schedule 1 controlled substance as an positional isomer of Alpha-methyltryptamine (AMT). [11]

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. ↑ Ott, Jonathan (1996). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company. ISBN   978-0-9614234-8-3.
  5. 1 2 3 4 5 6 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  6. 1 2 3 4 Shulgin A, Shulgin A (1997). TiHKAL: The Continuation . Berkeley: Transform Press. To my knowledge there have been no reports of oral activity of NMT, although its wide availability from botanic sources has encouraged some explorers to assay it. I have had one report that the smoking of 50–100 mg gave visuals that lasted for maybe 15 seconds.
  7. 1 2 3 4 5 Nen (4 December 2011). Entheogenic effects of NMT from Acacia. Entheogenesis Australis (EGA) Conference, Victoria, Australia, 2–5 December 2011 (PDF). Archived from the original on 5 April 2025. Retrieved 15 April 2025.{{cite conference}}: CS1 maint: bot: original URL status unknown (link)
  8. 1 2 3 4 5 Nen (13 July 2013). NMT: A Spatial Hallucinogen With Therapeutic Applications. Breaking Convention: The Second Multidisciplinary Conference on Psychedelic Consciousness, University of Greenwich, London, 12–14 July 2013.
  9. ↑ Foye WO, Lemke TL, Williams DA (2002). "Hallucinogens, Stimulatants, and Drugs of Abuse". Foye's Principles of Medicinal Chemistry (5th ed.). Lippincott Williams & Wilkins. p. 439. ISBN   9780683307375.
  10. ↑ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. N-Monoalkyltryptamines resemble the unsubstituted tryptamines in being good substrates for amine oxidases (Erspamer, 1955), a property which is reflected in their relatively poor hallucinogenic activity as compared to their N,N-dialkyl analogues. Thus, neither tryptamine nor its N-methyl derivative, both of which are oxidatively deaminated in rats to free (and conjugated) indole-3-acetic acids to the extent of 84·6 and 35·7 per cent respectively, produce behavioural changes in animals or man, whereas N,N-dimethyltryptamine, which is but little affected by amine oxidases, is a potent hallucinogen.
  11. ↑ "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.