7,N,N-TMT

7,N,N-trimethyltryptamine (7-methyl-DMT, 7-TMT), is a tryptamine derivative which 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).[4] 7-TMT also weakly inhibits reuptake of serotonin but with little effect on dopamine or noradrenaline reuptake.[5]

7,N,N-TMT
Identifiers
IUPAC name
  • 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)
SMILES
  • CC1=C(NC=C2CCN(C)C)C2=CC=C1
InChI
  • 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 Y
  • Key:PQSFTUCFMWBITK-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

See also

References
  1. 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. 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. 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. 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.
  5. 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.
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