1-Methyl-DMT

Last updated

1-Methyl-DMT
1-Methyl-DMT.svg
1-TMT 3D.png
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 class Serotonin 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
Formula C13H18N2
Molar mass 202.301 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]

Contents

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]

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. 1 2 3 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. 1 2 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. 1 2 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. 1 2 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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