7-MeO-DMT

7-MeO-DMT, or 7-OMe-DMT, also known as 7-methoxy-N,N-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family.^[1] It is the 7-methoxy derivative of the serotonergic psychedelic dimethyltryptamine (DMT) and is a positional isomer of 5-MeO-DMT, 4-MeO-DMT, and 6-MeO-DMT.^[1]

7-MeO-DMT

Clinical data
Other names	7-OMe-DMT; 7-Methoxy-DMT; 7-Methoxy-N,N-dimethyltryptamine
Drug class	Serotonin receptor modulator; Possible serotonergic psychedelic or hallucinogen
ATC code	None
Identifiers
IUPAC name 2-(7-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
PubChem CID	12017580
ChemSpider	23183416
ChEMBL	ChEMBL97017
Chemical and physical data
Formula	C13H18N2O
Molar mass	218.300 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN(C)CCC1=CNC2=C1C=CC=C2OC
InChI InChI=1S/C13H18N2O/c1-15(2)8-7-10-9-14-13-11(10)5-4-6-12(13)16-3/h4-6,9,14H,7-8H2,1-3H3 Key:GCEZYLSUTMYNRN-UHFFFAOYSA-N

Use and effects

7-MeO-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.^[2]

Pharmacology

Pharmacodynamics

In an early study using the isolated rat stomach fundus strip, the drug showed very low serotonin receptor affinity (A₂ = 4,677 nM) that was about 56-fold lower than that of 5-MeO-DMT.^[3][4][5] However, this assay was subsequently found to be an unreliable predictor of hallucinogenic activity.^[6]

In subsequent studies, 7-MeO-DMT bound to the serotonin 5-HT_2A receptor (K_i = 5,400–5,440 nM) and had 9- to 59-fold lower affinity than 5-MeO-DMT and 5- to 17-fold lower affinity than DMT.^[1][7][8] It showed no detectable affinity for the serotonin 5-HT_2C receptor (K_i = >10,000 nM), but did show affinity for the serotonin 5-HT_1A receptor (K_i = 1,760 nM).^[8] Its affinity for the serotonin 5-HT_1A receptor was 160-fold lower than that of 5-MeO-DMT and was 9-fold lower than that of DMT.^[8] 7-MeO-DMT has also been assessed at the serotonin 5-HT_1E and 5-HT_1F receptors (K_i = >10,000 nM and 2,620 nM, respectively).^[9]

7-MeO-DMT substitutes for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests.^[5] The drug was only briefly mentioned in Alexander Shulgin's 1997 book TiHKAL and is not known to have been tested in humans.^[3][2] Hence, it is unknown whether 7-MeO-DMT produces psychedelic effects in humans.^[3][2]

Chemistry

Analogues

Analogues of 7-MeO-DMT include dimethyltryptamine (DMT), 4-MeO-DMT, 5-MeO-DMT, and 6-MeO-DMT, among others.^[2][1]

History

7-MeO-DMT was first described in the scientific literature by at least 1968.^[10]

See also

• Substituted tryptamine