6-Methyl-5-MeO-DMT

6-Methyl-5-MeO-DMT, or 6-Me-5-MeO-DMT, also known as 5,6-MeOM-DMT, 5-MeO-6,N,N-TMT, or 6-methyl-5-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine and 5-methoxytryptamine families related to the psychedelic drug 5-MeO-DMT.^[1][2] It is the 6-methyl derivative of 5-MeO-DMT.^[1][2]

Other names6-Me-5-MeO-DMT; 5-Methoxy-6-methyl-DMT; 5,6-MeOM-DMT; 6-Methyl-5-methoxy-N,N-dimethyltryptamine; 6-Methylmebufotenin; 6,O-Dimethylbufotenin; 5-Methoxy-6,N,N-trimethyltryptamine; 5-MeO-6,N,N-TMT; 5-MeO-6-TMT

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist

ATC code

• None

CAS Number

• 74798-72-4

Quick facts Clinical data, Other names ...

6-Methyl-5-MeO-DMT

Clinical data
Other names	6-Me-5-MeO-DMT; 5-Methoxy-6-methyl-DMT; 5,6-MeOM-DMT; 6-Methyl-5-methoxy-N,N-dimethyltryptamine; 6-Methylmebufotenin; 6,O-Dimethylbufotenin; 5-Methoxy-6,N,N-trimethyltryptamine; 5-MeO-6,N,N-TMT; 5-MeO-6-TMT
Drug class	Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code	None
Identifiers
IUPAC name 2-(5-methoxy-6-methyl-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	74798-72-4
PubChem CID	12650290
ChemSpider	23118887
ChEMBL	ChEMBL20425
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1OC)C(=CN2)CCN(C)C
InChI InChI=1S/C14H20N2O/c1-10-7-13-12(8-14(10)17-4)11(9-15-13)5-6-16(2)3/h7-9,15H,5-6H2,1-4H3 Key:YPJSURIHBSXXMR-UHFFFAOYSA-N

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According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 6-Me-5-MeO-DMT is inactive in humans at doses of up to 15 mg via smoking.^[2] For comparison, 5-MeO-DMT was active at doses of 6 to 20 mg smoked.^[2]

Unlike 5-MeO-DMT and 7-Me-5-MeO-DMT, 6-Me-5-MeO-DMT is inactive as a serotonin receptor agonist in the rat fundus strip assay and does not substitute for 5-MeO-DMT in rodent drug discrimination tests.^[1][3] However, 6-Me-5-MeO-DMT has subsequently been found to be a potent and high-efficacy agonist of the serotonin 5-HT_2A and 5-HT_2C receptors but not of the serotonin 5-HT_2B receptor.^[4][5]

The chemical synthesis of 6-Me-5-MeO-DMT has been described.^[3][4]

6-Me-5-MeO-DMT was first described in the scientific literature by Richard Glennon and colleagues by 1980.^[3] Subsequently, it was further described by Shulgin in TiHKAL in 1997.^[2]