5-Methoxy-7,N,N-trimethyltryptamine

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5-Methoxy-7,N,N-trimethyltryptamine
5-MeO-7-TMT.png
Systematic (IUPAC) name
2-(5-Methoxy-7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
Clinical data
Legal status
?
Identifiers
CAS number 61018-77-7 N freebase
74798-76-8 oxalate salt
ATC code ?
PubChem CID 12338919
ChemSpider 10578304 YesY
ChEMBL CHEMBL20243 YesY
Chemical data
Formula C14H20N2O 
Mol. mass 232.32 g/mol
 N (what is this?)  (verify)

5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as an agonist at the 5-HT2 serotonin receptors.[1][2] In animal tests, both 7,N,N-TMT and 5-MeO-7,N,N-TMT produced behavioural responses similar to those of psychedelic drugs such as DMT and 5-MeO-DMT, but compounds with larger 7-position substituents such as 7-ethyl-DMT and 7-bromo-DMT did not produce psychedelic-appropriate responding despite high 5-HT2 receptor binding affinity, suggesting these may be antagonists or weak partial agonists for the 5-HT2 receptors.[3] The related compound 7-MeO-MiPT (cf. 5-MeO-MiPT) was also found to be inactive, suggesting that the 7-position has poor tolerance for bulky groups at this position, at least if agonist activity is desired.[4]

See also[edit]

References[edit]

  1. ^ Benington F, Morin RD, Bradley RJ. 7-(N,N-Trimethyl)-5-methoxytryptamine. Journal of Heterocyclic Chemistry 1976; 13(4):749-751. doi:10.1002/jhet.1976.5570130412
  2. ^ 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. 
  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): 1222–6. doi:10.1021/jm00185a014. PMID 6779006. 
  4. ^ Repke DB, Grotjahn DB, Shulgin AT (July 1985). "Psychotomimetic N-methyl-N-isopropyltryptamines. Effects of variation of aromatic oxygen substituents". Journal of Medicinal Chemistry 28 (7): 892–6. doi:10.1021/jm00145a007. PMID 4009612.