6-Methyl-5-MeO-DMT

6-Methyl-5-MeO-DMT
Clinical data
Other names6-Me-5-MeO-DMT; 5-Methoxy-6-methyl-DMT; 5,6-MeOM-DMT; 6-Methyl-5-methoxy-N,N-dimethyltryptamine; 6-Methylmebufotenin; 6,O-Dimethylbufotenin; 5-Methoxy-6,N,N-trimethyltryptamine; 5-MeO-6,N,N-TMT; 5-MeO-6-TMT
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • 2-(5-methoxy-6-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CC1=CC2=C(C=C1OC)C(=CN2)CCN(C)C
  • InChI=1S/C14H20N2O/c1-10-7-13-12(8-14(10)17-4)11(9-15-13)5-6-16(2)3/h7-9,15H,5-6H2,1-4H3
  • Key:YPJSURIHBSXXMR-UHFFFAOYSA-N

6-Methyl-5-MeO-DMT, or 6-Me-5-MeO-DMT, also known as 5,6-MeOM-DMT, 5-MeO-6,N,N-TMT, or 6-methyl-5-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine and 5-methoxytryptamine families related to the psychedelic drug 5-MeO-DMT.[1][2] It is the 6-methyl derivative of 5-MeO-DMT.[1][2]

According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 6-Me-5-MeO-DMT is inactive in humans at doses of up to 15 mg via smoking.[2] For comparison, 5-MeO-DMT was active at doses of 6 to 20 mg smoked.[2]

Unlike 5-MeO-DMT and 7-Me-5-MeO-DMT, 6-Me-5-MeO-DMT is inactive as a serotonin receptor agonist in the rat fundus strip assay and does not substitute for 5-MeO-DMT in rodent drug discrimination tests.[1][3] However, 6-Me-5-MeO-DMT has subsequently been found to be a potent and high-efficacy agonist of the serotonin 5-HT2A and 5-HT2C receptors but not of the serotonin 5-HT2B receptor.[4][5]

The chemical synthesis of 6-Me-5-MeO-DMT has been described.[3][4]

6-Me-5-MeO-DMT was first described in the scientific literature by Richard Glennon and colleagues by 1980.[3] Subsequently, it was further described by Shulgin in TiHKAL in 1997.[2]

See also

References

  1. 1 2 3 Nichols DE (1985). "Use of Chemical Approaches to Probe Serotonin Receptor Topography". International Symposium on Medicinal Chemistry Proceedings (PDF). Vol. 12. pp. 103–115.
  2. 1 2 3 4 5 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "One desoxy analogue warrants mention. This is known as 5-methoxy-6-methyl-DMT (5,6-MeOM-DMT) or as 5-methoxy-6,N,N-trimethyltryptamine (5-MeO-6,N,N-TMT), where the 6-methoxy group is, in effect, replaced with a 6-methyl group. Having a DMT skeleton, it was assayed parenterally, and even at 15 milligrams (smoking) there was nothing noted. This is a level that would have been dramatic had there been no substitution at that 6-position. Some of the historical background of an oxygen at this position is discussed in the 6-HO-DMT recipe."
  3. 1 2 3 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.
  4. 1 2 "Compounds". Google Patents. 23 December 2022. Retrieved 14 May 2026.
  5. ↑ Sabnis RW (September 2025). "Novel Compounds as 5‑HT2A Agonists for Treating Mental Illness or CNS Disorders". ACS Medicinal Chemistry Letters. 16 (9): 1711–1712. doi:10.1021/acsmedchemlett.5c00460. PMC 12434509. PMID 40959240.
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