7,N,N-TMT

7,N,N-TMT
Clinical data
Other names7,N,N-Trimethyltryptamine; 7,N,N-TMT; 7-TMT; 7-Methyl-N,N-dimethyltryptamine; 7-Methyl-DMT; 7-Me-DMT
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
Identifiers
  • 2-(7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H18N2
Molar mass202.301 g·mol−1
3D model (JSmol)
  • CC1=C(NC=C2CCN(C)C)C2=CC=C1
  • InChI=1S/C13H18N2/c1-10-5-4-6-12-11(7-8-15(2)3)9-14-13(10)12/h4-6,9,14H,7-8H2,1-3H3 checkY
  • Key:PQSFTUCFMWBITK-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

7,N,N-trimethyltryptamine (7,N,N-TMT or 7-TMT), also known as 7-methyl-DMT, is a serotonin receptor modulator and psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).[1][2][3] It was first described by 1978[1][4] and was encountered online as a novel designer drug in 2024.[5]

Use and effects

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

Interactions

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

Pharmacology

Pharmacodynamics

7-TMT acts as an agonist of 5-HT2 receptors.[1][2][3] In animal tests, both 7-TMT and its 5-methoxy derivative 5-MeO-7-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT, but the larger 7-ethyl and 7-bromo derivatives of DMT did not produce psychedelic responses despite having higher 5-HT2 receptor affinity in vitro (cf. DOBU, DOAM).[7] 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.[4]

Chemistry

Synthesis

The chemical synthesis of 7,N,N-TMT has been described.[4]

Analogues

Analogues of 7-methyl-DMT include dimethyltryptamine (DMT), 5-MeO-7-TMT (5-MeO-7,N,N-TMT), 7-MeO-DMT, 7-hydroxy-DMT, 7-methyl-AET, 7-MeO-DiPT, 7-MeO-MiPT, 7-chloro-AMT, 1-methyl-DMT, 2-methyl-DMT, 4-methyl-DMT, 5-methyl-DMT, and 6-methyl-DMT, among others.[6]

History

7,N,N-TMT was first described in the scientific literature by Richard Glennon and colleagues by 1978.[1][4] It was encountered online as a novel designer drug in 2024.[5]

See also

References

  1. ^ a b c d Glennon RA, Liebowitz SM, Mack EC (August 1978). "Serotonin receptor binding affinities of several hallucinogenic phenylalkylamine and N,N-dimethyltryptamine analogues". Journal of Medicinal Chemistry. 21 (8): 822–5. doi:10.1021/jm00206a022. PMID 278843.
  2. ^ a b Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–32. doi:10.1021/jm00190a014. PMID 430481.
  3. ^ a b 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): 291–7. doi:10.1016/0014-2999(88)90432-3. PMID 3350047.
  4. ^ a b c d Glennon RA, Martin B, Johnson KM, End D (January 1978). "7,N,N-Trimethyltryptamine: a selective inhibitor of synaptosomal serotonin uptake". Research Communications in Chemical Pathology and Pharmacology. 19 (1): 161–4. PMID 625585.
  5. ^ a b "7-Me-DMT (7-TMT)". АИПСИН (in Russian). Retrieved 1 January 2026.
  6. ^ a b Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  7. ^ Glennon RA, Schubert E, Jacyno JM, Rosecrans JA (November 1980). "Studies on several 7-substituted N,N-dimethyltryptamines". Journal of Medicinal Chemistry. 23 (11): 1222–6. doi:10.1021/jm00185a014. PMID 6779006.
allikas: https://en.wikipedia.org/wiki/7-Methyl-DMT