6-MeO-DMT

6-MeO-DMT
Clinical data
Other names	6-Methoxy-N,N-dimethyltryptamine; 6-Methoxy-DMT; 6-Methoxy-N,N-DMT; 6-OMe-DMT
Drug class	Serotonin receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist
Identifiers
	IUPAC name 2-(6-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	2426-88-2 ;
PubChem CID	12017579;
ChemSpider	23118889;
ChEMBL	ChEMBL281408;
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(=C2)OC;
	InChI InChI=1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-8-11(16-3)4-5-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3; Key:AWOWBKXVYZRYSP-UHFFFAOYSA-N;

6-MeO-DMT, or 6-methoxy-N,N-dimethyltryptamine, also known as 6-OMe-DMT, is a serotonergic drug of the tryptamine family. It is the 6-methoxy derivative of the serotonergic psychedelic N,N-dimethyltryptamine (DMT) and is a positional isomer of the psychedelic 5-MeO-DMT.

Similarly to analogues like DMT and 5-MeO-DMT, 6-MeO-DMT acts as a serotonin 5-HT_2A receptor agonist as well as a non-selective agonist of many other serotonin receptors. However, in contrast to these agents, but similarly to certain other serotonin 5-HT_2A receptor agonists like 6-fluoro-DET, 2-bromo-LSD, lisuride, 25N-N1-Nap, and tabernanthalog, 6-MeO-DMT does not produce the head-twitch response (HTR) or other psychedelic-like effects in animals and hence appears to be non-hallucinogenic. Similarly, 6-MeO-DMT failed to substitute for DOM in rodent drug discrimination tests. On the other hand, it did substitute for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests, with about 4-fold lower potency than 5-MeO-DMT. 6-MeO-DMT has yet to be tested in humans.

In addition to its apparent lack of hallucinogenicity, 6-MeO-DMT shows dramatically reduced potency as an agonist of all of the serotonin receptors compared to 5-MeO-DMT. Its affinity for the serotonin 5-HT_2A receptor was 12- to 43-fold lower than that of 5-MeO-DMT and was 6-fold lower than that of DMT and its affinity for the serotonin 5-HT_1A receptor was 110-fold lower relative to 5-MeO-DMT.

6-MeO-DMT was first described in the scientific literature by 1968. It was specifically assessed in a structure–activity relationship (SAR) animal study of serotonergic tryptamines. The drug's lack of hallucinogen-like effects in animals was first described by at least 1983.