6-Hydroxy-DMT


6-Hydroxy-DMT, or 6-HO-DMT, also known as 6-hydroxy-N,''N''-dimethyltryptamine, is a serotonin receptor modulator of the tryptamine family related to the psychedelic drug dimethyltryptamine. It is a major metabolite of DMT in rodents but a minor metabolite of DMT in humans. The drug is the 6-hydroxy analogue of DMT and is a positional isomer of bufotenin and psilocin.

Use and effects

6-Hydroxy-DMT was completely inactive in terms of psychoactive and autonomic effects at doses of 0.75 to 1mg/kg by intramuscular injection in humans. The drug was said to be indistinguishable from placebo. Conversely, DMT produced strong hallucinogenic effects at the same doses.

Pharmacology

Although it was inactive as a psychedelic in humans, 6-hydroxy-DMT has been found to produce pharmacological effects in animals, albeit with diminished potency compared to dimethyltryptamine. As examples, in terms of behavioral effects, 6-hydroxy-DMT was ≥3-fold less potent in rats, >10-fold less potent in cats, and 3-fold less potent in monkeys. It was suggested by Richard Glennon and colleagues that the reduced activity of 6-hydroxy-DMT may be due to its greater hydrophilicity and reduced ability to penetrate the blood–brain barrier analogously to the case of bufotenin.
Subsequent research assessed 6-hydroxy-DMT at the serotonin receptors in vitro. It was found to have detectable but very low affinity for the serotonin 5-HT2 receptors.

Chemistry

Properties

The predicted log P of 6-HO-DMT is 2.4. For comparison, the predicted log P of psilocin is 2.1 and of bufotenin is 1.2.

Analogues

s of 6-hydroxy-DMT include 6-hydroxytryptamine, dimethyltryptamine, 6-HO-DMT, 6-MeO-DMT, 5,6-MDO-DMT, 6-methyl-DMT, and 6-fluoro-DMT, among others.

History

6-Hydroxy-DMT was first described in the scientific literature by at least 1962.

Society and culture

Legal status

United States

6-Hydroxy-DMT is a Schedule I controlled substance in the United States as a positional isomer of psilocin.