5-Methoxy-7,N,N-trimethyltryptamine

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]

5-Methoxy-7,N,N-trimethyltryptamine

Identifiers
IUPAC name 2-(5-Methoxy-7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	61018-77-7^N freebase 74798-76-8 oxalate salt
PubChem CID	12338919
ChemSpider	10578304^Y
ChEMBL	ChEMBL20243^Y
CompTox Dashboard (EPA)	DTXSID40491731
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC1=C(NC=C2CCN(C)C)C2=CC(OC)=C1
InChI InChI=1S/C14H20N2O/c1-10-7-12(17-4)8-13-11(5-6-16(2)3)9-15-14(10)13/h7-9,15H,5-6H2,1-4H3^Y Key:YGAOMGVUIWNFMD-UHFFFAOYSA-N^Y
^NY (what is this?)  (verify)

See also

• 5-MeO-2-TMT

References

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.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.