6-Methyl-DMT

Last updated

6-Methyl-DMT
6-Me-DMT structure.png
Clinical data
Other names6-Me-DMT; 6-Methyl-N,N-dimethyltryptamine; 6,N,N-Trimethyltryptamine; 6,N,N-TMT; 6-TMT
Drug class Serotonin receptor modulator
ATC code
  • None
Identifiers
  • N,N-dimethyl-2-(6-methyl-1H-indol-3-yl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
Formula C13H18N2
Molar mass 202.301 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(C=C1)C(=CN2)CCN(C)C
  • InChI=1S/C13H18N2/c1-10-4-5-12-11(6-7-15(2)3)9-14-13(12)8-10/h4-5,8-9,14H,6-7H2,1-3H3
  • Key:ODOKWPMMQYDQIA-UHFFFAOYSA-N

6-Methyl-DMT, or 6-Me-DMT, also known as 6-methyl-N,N-dimethyltryptamine or as 6,N,N-trimethyltryptamine (6,N,N-TMT or 6-TMT), is a serotonin receptor modulator of the tryptamine family related to dimethyltryptamine (DMT). [1] [2] It is the 6-methyl derivative of DMT. [1] [2]

Contents

Use and effects

6-Methyl-DMT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). [3]

Pharmacology

Pharmacodynamics

6-Methyl-DMT showed about half the affinity of DMT for the ketanserin-labeled serotonin 5-HT2 receptor (Ki = 2,500 nM and 1,200 nM, respectively). [1] [4] The drug did not substitute for 5-MeO-DMT in rodent drug discrimination tests. [2] According to David E. Nichols, 6-substituted tryptamines in general may be inactive as serotonergic psychedelics. [5] However, 6-fluoro-AMT is known to be robustly active as a psychedelic. [6] [7]

Chemistry

Synthesis

The chemical synthesis of 6-methyl-DMT has been described. [2]

Analogues

Analogues of 6-methyl-DMT include dimethyltryptamine (DMT), 6-MeO-DMT, 6-MeO-DiPT, 6-MeO-MiPT, 6-hydroxy-DMT, 6-hydroxy-DET, 6-fluoro-DMT, 6-fluoro-DET, 6-fluoro-AMT, O-4310 (1-iPr-6-F-4-HO-DMT), 1-methyl-DMT, 2-methyl-DMT, 4-methyl-DMT, 5-methyl-DMT, and 7-methyl-DMT, among others. [3]

History

6-Methyl-DMT was first described in the scientific literature by Richard Glennon and colleagues by 1980. [2]

See also

References

  1. 1 2 3 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.
  2. 1 2 3 4 5 Glennon RA, Schubert E, Jacyno JM, Rosecrans JA (November 1980). "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry. 23 (11): 1222–1226. doi:10.1021/jm00185a014. PMID   6779006.
  3. 1 2 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  4. ↑ Schulze-Alexandru M, Kovar KA, Vedani A (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances". Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN   0931-8771 . Retrieved 6 January 2026.
  5. ↑ Nichols DE (1985). "Use of chemical approaches to probe serotonin receptor topography." (PDF). 8th International Symposium on Medicinal Chemistry Proceedings. Vol. 12. pp. 103–115.
  6. ↑ Morris H (2010). "Life is a Cosmic Giggle on the Breath of the Universe. A Tour of Gordon Todd Skinner's Subterranean LSD Palace". Vice Magazine. Archived from the original on 2014-10-13. Retrieved 2017-08-23.
  7. ↑ "Unusual Analogues: Drugs Used by Gordon Todd Skinner". thislandpress.com. This Land Press. Archived from the original on 17 April 2016. Retrieved 8 April 2016.
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