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. It is the 6-methoxy derivative of the serotonergic psychedelic N'',N-dimethyltryptamine and is a positional isomer of the psychedelic 5-MeO-DMT.

Use and effects

6-MeO-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL and its properties and effects were not described.

Pharmacology

Pharmacodynamics

Similarly to analogues like DMT and 5-MeO-DMT, 6-MeO-DMT acts as a serotonin 5-HT2A 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-HT2A 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 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-HT2A 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-HT1A receptor was 110-fold lower relative to 5-MeO-DMT.

Chemistry

Analogues

s of 6-MeO-DMT include dimethyltryptamine, 6-methoxytryptamine, 6-hydroxy-DMT, 6-methyl-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.

History

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

Society and culture

Legal status

United States

6-MeO-DMT is not an explicitly controlled substance in the United States, but may be considered a Schedule I controlled substance in this country as it is a positional isomer of 5-MeO-DMT.