1-Methyl-DMT

1-Methyl-DMT
Clinical data
Other names1-Me-DMT; 1-Methyl-N,N-dimethyltryptamine; 1,N,N-Timethyltryptamine; 1,N,N-TMT; 1-TMT; N,N,1-Trimethyltryptamine
Drug classSerotonin receptor modulator; Psychoplastogen
ATC code
  • None
Identifiers
  • N,N-dimethyl-2-(1-methylindol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • CN1C=C(C2=CC=CC=C21)CCN(C)C
  • InChI=1S/C13H18N2/c1-14(2)9-8-11-10-15(3)13-7-5-4-6-12(11)13/h4-7,10H,8-9H2,1-3H3
  • Key:WYFWKMQPMCPKLZ-UHFFFAOYSA-N

1-Methyl-DMT, or 1-Me-DMT, also known as 1-methyl-N,N-dimethyltryptamine or as 1,N,N-trimethyltryptamine (1,N,N-TMT or 1-TMT), is a serotonin receptor modulator of the tryptamine family related to dimethyltryptamine (DMT) and lespedamine (1-methoxy-DMT).[1]

Pharmacology

Pharmacodynamics

1-Methyl-DMT appears to have similar affinity for serotonin receptors as DMT, but is more toxic than DMT in rodents.[1][2][3] In another study, it showed 3-fold higher affinity for the serotonin 5-HT2A receptor than DMT.[4][5] In a further study, it showed abolished affinity for the 5-HT1E receptor and 30-fold lower affinity for the serotonin 5-HT1F receptor than DMT.[6] 1-Methyl-DMT shows comparable psychoplastogenic effects in preclinical research to DMT.[7][8]

Chemistry

Synthesis

The chemical synthesis of 1-methyl-DMT has been described.[7]

Analogues

Analogues of 1-methyl-DMT include dimethyltryptamine (DMT), 1-methyltryptamine, lespedamine (1-MeO-DMT), 1-methylpsilocin (1-Me-4-HO-DMT; CMY-16), 2-methyl-DMT, 4-methyl-DMT, 5-methyl-DMT, 6-methyl-DMT, and 7-methyl-DMT, among others.[1]

History

The drug was briefly mentioned by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved).[1] 1-Methyl-DMT was first described in the scientific literature by Richard Glennon and colleagues in 1979.[2][3]

See also

References

  1. ^ a b c d Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "1-Methyl-DMT". "Several simple substitution derivatives of DMT are known. Those that are known to be psychedelic have their own recipes, of course, but the others will be summarized here. The 1-methyl homologue of DMT (1,N,N-trimethyltryptamine) can be prepared from DMT in KOH and DMSO, with CH3I. It forms a picrate salt which melts at 175–179 °C, and bioxalate, mp 174–176 °C. It is more toxic than DMT in rats, but has an identical serotonin binding capacity. The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT."
  2. ^ a b Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–432. doi:10.1021/jm00190a014. PMID 430481.
  3. ^ a b Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities". Psychopharmacology. 68 (2): 155–158. doi:10.1007/BF00432133. PMID 6776558.
  4. ^ Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens". European Journal of Pharmacology. 145 (3): 291–297. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
  5. ^ Glennon RA, Seggel MR (14 November 1989). "Interaction of Phenylisopropylamines with Central 5-HT2 Receptors". Probing Bioactive Mechanisms. ACS Symposium Series. Vol. 413. Washington, DC: American Chemical Society. pp. 264–280. doi:10.1021/bk-1989-0413.ch018. ISBN 978-0-8412-1702-7.
  6. ^ Klein MT, Dukat M, Glennon RA, Teitler M (June 2011). "Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships". The Journal of Pharmacology and Experimental Therapeutics. 337 (3): 860–867. doi:10.1124/jpet.111.179606. PMC 3101003. PMID 21422162.
  7. ^ a b Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, et al. (February 2020). "Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies". Journal of Medicinal Chemistry. 63 (3): 1142–1155. doi:10.1021/acs.jmedchem.9b01404. PMC 7075704. PMID 31977208.
  8. ^ Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021). "Psychedelic-inspired drug discovery using an engineered biosensor". Cell. 184 (10): 2779–2792.e18. doi:10.1016/j.cell.2021.03.043. PMC 8122087. PMID 33915107.
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