Chemistry:5-Methoxy-7,N,N-trimethyltryptamine

Short description: Chemical compound

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
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)

5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), is a tryptamine derivative which acts as a partial agonist at the 5-HT₂ serotonin receptors, with an EC₅₀ of 63.9 nM and an efficacy of 66.2% at 5-HT_2A (vs 5-HT), and weaker activity at 5-HT_2B and 5-HT_2C. 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. 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.

See also

• 5-MeO-2-TMT
• 7F-5-MeO-MET