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N-Methyltryptamine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
N-Methyltryptamine
Clinical data
Other namesNMT; Methyltryptamine;N-MT; Monomethyltryptamine; Dipterine; PAL-152; PAL152
Routes of
administration
Smoking,oral (with anMAOITooltip monoamine oxidase inhibitor)[1][2][3]
Drug classNon-selectiveserotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen
Legal status
Legal status
Pharmacokinetic data
Duration of actionSeconds to minutes[1][2][3]
Identifiers
  • 2-(1H-indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.000.462Edit this at Wikidata
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
  (verify)

N-Methyltryptamine (NMT), also known asmonomethyltryptamine, is achemical compound of thetryptamine family and anaturally occurring compound found in the human body and certain plants.

It isbiosynthesized in humans fromtryptamine by certainN-methyltransferaseenzymes, such asindolethylamineN-methyltransferase.[4][5] It is a known component in human urine.[6] NMT is analkaloid derived fromL-tryptophan that has been found in thebark,shoots andleaves of several plantgenera, includingVirola,Acacia,Mimosa, andDesmanthus—often together with the relatedcompoundsN,N-dimethyltryptamine (DMT) and5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).[7]

NMT acts as aserotonin receptor agonist andserotonin releasing agent[8] and is said to producehallucinogenic effects in humans.[1][2][3]

Use and effects

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Orally administered NMT appears to produce nopsychoactive effects, likely as a result of extensivefirst-pass metabolism.[9]

According to Roger W. Brimblecombe and colleagues, NMT is inactive in humans, with few details provided.[10] On the other hand, according toAlexander Shulgin and others, NMT is active vianon-oralroutes.[1][2][3] It has been said to producepsychedelic effects at doses of 50 to 120 mg bysmoking orvaporization, with aduration of seconds to minutes.[1][2][3] Based on preliminary reports, NMT is reported to producevisuals, but its effects are described as primarilyspatial in nature, among other effects.[1][2][3]

NMT has also been reported to be orally active incombination with amonoamine oxidase inhibitor (MAOI).[2][3]

Interactions

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See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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NMT is known to act as apotentserotonin5-HT2A receptorfull agonist (EC50Tooltip half-maximal effective concentration = 50.7 nM;EmaxTooltip maximal efficacy = 96%).[8] It has been reported to be inactive in activating theβ-arrestin pathway of the receptor and hence appears to be abiased agonist of the serotonin 5-HT2A receptor.[8] The drug is not an agonist of the serotonin5-HT1A receptor.[8]

In addition to its serotonin 5-HT2A receptor agonism, NMT is a potentserotonin releasing agent (EC50 = 22.4 nM).[8] It also releasesdopamine andnorepinephrine much more weakly (EC50 = 321 nM and 733 nM, respectively; 14- and 33-fold less than for serotonin, respectively).[8]

Society and culture

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Legal status

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

See also

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References

[edit]
  1. ^abcdefShulgin 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.
  2. ^abcdefgNen (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. Retrieved15 April 2025.{{cite conference}}: CS1 maint: bot: original URL status unknown (link)
  3. ^abcdefgNen (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.
  4. ^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.
  5. ^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.
  6. ^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.
  7. ^Ott, Jonathan (1996).Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History. Natural Products Company.ISBN 978-0-9614234-8-3.
  8. ^abcdefBlough 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.
  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.

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