6-Hydroxy-DET

6-Hydroxy-DET, or 6-HO-DET, also known as 6-hydroxy-N,N-diethyltryptamine, is a possible psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). "6-HO-DET has been observed to be a minor human metabolite of DET, with the excretion of about 20% of the administered dose as the glucoronide conjugate. In a study with normal and schizophrenic patients, a positive correlation was observed between the amount of 6-HO-DET excreted and the intensity of the experience. Also, there was a suggestion that the schizophrenics produced greater amounts of this metabolite. This led to a hypothesis that perhaps it was an active factor in the generation of the intoxicated state. In principle, as with bufotenine, that bare, exposed polar hydroxyl group should make its entry to the brain quite difficult. But, on the other hand, if it were generated there from DET after it had gotten into the brain, entry would not be a concern and the lipophilic barrier could serve to make its exit difficult. Then, if it were an effective compound, it might well be a long acting one. There is an early report of the self-administration intramuscularly, within a single subject, of 10 milligrams 6-HO-DET with the description of what appeared to be DET-like effects from about the second to fourth hour. Although this report suggested that it was several times more potent than DET, it has never been replicated and it does not jibe too well with the 6-HO-DMT report below." [...] "And it was at the last of these, at Lexington, that this hydroxylated DMT study was done. The results were negative, to the disappointment of the researchers. It is pretty generally accepted that 6-HO-DMT is inactive. I am not too surprised. There are so few things with open and exposed hydroxyl groups that succeed in making it through the lipid barriers to the brain." It is the 6-hydroxy derivative of diethyltryptamine (DET). The drug is a notable metabolite of DET.

Use and effects According to Alexander Shulgin in his book TiHKAL (Tryptamines I Have Known and Loved), 6-HO-DET has been reported to be active at a dose of 10mg by intramuscular injection. Lower doses of 1 to 2mg were inactive, whereas 5mg produced threshold effects. The drug at a dose of 10mg was said to produce psychedelic effects very similar to those with 60mg diethyltryptamine (DET), with these effects starting after 1hour and lasting 2 to 3hours. Based on this report, the drug would be about 5 to 6times more potent than DET in humans. However, this report of 6-HO-DET's properties and effects is a second-hand early account in a single subject provided by Stephen Szara and colleagues and has not been replicated. Moreover, it is seemingly inconsistent with the inactivity of the closely related compounds 6-HO-DMT, 6-MeO-DMT, and 6-fluoro-DET. Relatedly, Shulgin wrote in TiHKAL that it is generally accepted that 6-HO-DET is inactive.

Interactions

Pharmacology Pharmacodynamics The effects of 6-HO-DET in animals have been studied. It was found to be much more potent than diethyltryptamine (DET) in terms of producing behavioral effects in rodents.

Pharmacokinetics Alexander Shulgin has noted that 6-HO-DET may have poor blood–brain barrier permeability due to its exposed hydroxyl group and consequent polarity analogously to bufotenin (5-HO-DMT).

Chemistry Properties The predicted log P of 6-HO-DET is 3.1. For comparison, the predicted log P of 6-HO-DMT is 2.4, of 4-HO-DET is 2.7, of 5-HO-DET is 1.9, and of bufotenin (5-HO-DMT) is 1.2.

Analogues Analogues of 6-HO-DET include diethyltryptamine (DET), 6-hydroxytryptamine (6-HT or 6-HO-T), 6-HO-DMT, 6-MeO-DMT, 6-methyl-DMT, 6-fluoro-DET, psilocin (4-HO-DMT), 4-HO-DET, bufotenin (5-HO-DMT), 7-HO-DMT, 5-HO-DET, 5-HO-DPT, and 5-HO-DiPT, among others.

History 6-HO-DET was first described in the scientific literature by Stephen Szara and colleagues by 1962. It was identified as a major active metabolite of diethyltryptamine (DET). In addition, they found that excretion of 6-HO-DET with DET administration correlated with DET's hallucinogenic effects and that 6-HO-DET was much more potent than DET in humans based on preliminary observations. Consequently, Szara and colleagues theorized that 6-hydroxylation of psychedelic tryptamines like dimethyltryptamine (DMT), DET, and α-methyltryptamine (AMT) was importantly involved in their hallucinogenic effects. However, this hypothesis was later found to be incorrect and was abandoned.

6-Hydroxy-DET

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