5-MeO-2-TMT

5-MeO-2-TMT
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name 2-(5-methoxy-2-methyl-H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	67292-68-6;
PubChem CID	49756;
ChemSpider	45143 ;
UNII	XZ2CCP18I2;
ChEMBL	ChEMBL7143 ;
CompTox Dashboard (EPA)	DTXSID10217627 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=C(C2=C(N1)C=CC(=C2)OC)CCN(C)C;
	InChI InChI=1S/C14H20N2O/c1-10-12(7-8-16(2)3)13-9-11(17-4)5-6-14(13)15-10/h5-6,9,15H,7-8H2,1-4H3 ; Key:ACEHBQPPDDGCGZ-UHFFFAOYSA-N ;
	(verify)

5-Methoxy-2,N,N-trimethyltryptamine (5-MeO-2,N,N-TMT, 5-MeO-TMT) is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL ("Tryptamines i Have Known And Loved").^[1] 5-MeO-TMT is claimed to show psychoactive effects at a dosage of 75–150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT_2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.

References

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