6-Hydroxy-DMT

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6-Hydroxy-DMT
Clinical data
Other names6-HDMT; 6-HO-DMT; 6-OH-DMT; 6-Hydroxy-N,N-dimethyltryptamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 3-[2-(dimethylamino)ethyl]-1H-indol-6-ol
CAS Number
PubChem CID
ChemSpider
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
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Chemical and physical data
FormulaC12H16N2O
Molar mass204.273 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=CC(=C2)O
  • InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-7-10(15)3-4-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3
  • Key:WUQMRWPLIMXBDX-UHFFFAOYSA-N

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 (DMT).[1][2][3][4][5] It is a major metabolite of DMT in rodents but a minor metabolite of DMT in humans.[4][6][7] The drug is the 6-hydroxy analogue of DMT and is a positional isomer of bufotenin (5-HO-DMT) and psilocin (4-HO-DMT).[2][3][8]

Use and effects

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6-Hydroxy-DMT was completely inactive in terms of psychoactive and autonomic effects at doses of 0.75 to 1 mg/kg (~53–70 mg for a 70-kb person) by intramuscular injection in humans.[1][2][5] The drug was said to be indistinguishable from placebo.[5] Conversely, DMT produced strong hallucinogenic effects at the same doses.[5]

Pharmacology

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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 (DMT).[4][2][8][9] 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.[4] 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.[8]

Subsequent research assessed 6-hydroxy-DMT at the serotonin receptors in vitro.[7] It was found to have detectable but very low affinity for the serotonin 5-HT2 receptors (Ki ≥ 6,300–19,000 nM).[7]

Chemistry

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Properties

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The predicted log P of 6-HO-DMT is 2.4.[10] For comparison, the predicted log P of psilocin (4-HO-DMT) is 2.1[11] and of bufotenin (5-HO-DMT) is 1.2.[12]

Analogues

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Analogues of 6-hydroxy-DMT include 6-hydroxytryptamine (6-HT or 6-HO-T), dimethyltryptamine (DMT), 6-HO-DMT, 6-MeO-DMT, 5,6-MDO-DMT, and 6-fluoro-DMT, among others.

History

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6-Hydroxy-DMT was first described in the scientific literature by at least 1962.[13]

See also

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References

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  1. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value). "6-HO-DMT is a minor metabolite of DMT in man, and it was studied for the same reasons. Could this compound play a role in explaining the activity of the parent dialkylamine? It was explored in a series of subjects who had responded spectacularly to DMT. The five volunteers in this study were former opium addicts who were serving sentences for violation of United States narcotics laws. They were administered 6-HO-DMT at either 0.75 mg/kg (one subject) or 1.0 mg/kg (four subjects) and reported no differences from the inactive placebo control. The objective measures (blood pressure, respiration and heart rate, pupillary dilation) confirmed this absence of activity at this level. The active control drug was DMT itself, and it showed the expected responses in all regards." [...] "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 that protect to the brain."
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