6-MeO-DMT

6-MeO-DMT, or 6-methoxy-N,N-dimethyltryptamine, also known as 6-OMe-DMT, is a serotonergic drug of the tryptamine family.^[1][2][3] 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.^[3][4]

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 Y
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

Use and effects

6-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.^[5]

Pharmacology

Pharmacodynamics

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.^[1][2][6][3] 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.^[1][2][7][6] Similarly, 6-MeO-DMT failed to substitute for DOM in rodent drug discrimination tests.^[8] 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.^[9] 6-MeO-DMT has yet to be tested in humans.^[10][2]

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.^[6] 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.^[3][1][11]

Chemistry

Analogues

Analogues of 6-MeO-DMT include dimethyltryptamine (DMT), 6-methoxytryptamine (6-MT or 6-MeO-T), 6-hydroxy-DMT (6-HO-DMT), 6-fluoro-DMT, 4-MeO-DMT, 5-MeO-DMT, and 7-MeO-DMT, among others. Some further analogues include the isotryptamines 5-MeO-isoDMT, 6-MeO-isoDMT, and zalsupindole ((R)-5-MeO-α-Me-isoDMT).

History

6-MeO-DMT was first described in the scientific literature by 1968.^[12][13][14] It was specifically assessed in a structure–activity relationship (SAR) animal study of serotonergic tryptamines.^[12][13] The drug's lack of hallucinogen-like effects in animals was first described by at least 1983.^[8]

See also

• Substituted tryptamine
• Non-hallucinogenic 5-HT_2A receptor agonist