5-Methoxy-7,N,N-trimethyltryptamine

5-MeO-7,N,N-TMT
Clinical data
Other names	5-MeO-7,N,N-TMT; 5-MeO-7-TMT; 7-Me-5-MeO-DMT; 7-Methyl-5-MeO-DMT
Identifiers
	IUPAC name 2-(5-Methoxy-7-methyl-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	61018-77-7 freebase; 74798-76-8 oxalate salt;
PubChem CID	12338919;
ChemSpider	10578304 ;
UNII	JC6AF6KXW9;
ChEMBL	ChEMBL20243 ;
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 ; Key:YGAOMGVUIWNFMD-UHFFFAOYSA-N ;
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5-Methoxy-7,N,N-trimethyltryptamine (5-MeO-7,N,N-TMT, 5-MeO-7-TMT), also known as 7-Me-5-MeO-DMT, 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.^[1]^[2]^[3] 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.^[4] 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.^[5]