4-HO-DBT

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported that a 20mg dose of 4-HO-DBT orally produced no effects. However, this compound has subsequently been sold as a "research chemical" and anecdotal reports suggest that at higher doses 4-HO-DBT is indeed an active hallucinogen, although somewhat weaker than other similar tryptamine derivatives.

Interactions

Chemistry

Properties

4-HO-DBT is found either as its crystalline hydrochloride salt or as an oily or crystalline base.

Synthesis

The chemical synthesis of 4-HO-DBT has been described.

Isomers

Several different isomers of 4-HO-DBT could be made, including 4-HO-DiBT, 4-HO-DsBT, and 4-HO-DtBT, but of these only the isobutyl isomer 4-HO-DiBT was synthesized by Alexander Shulgin (melting point 152 to 154°C) and was also found to be inactive at a 20mg dose. The serotonin receptor interactions of these isomers have been studied. 4-HO-DiBT showed 43-fold lower affinity and 4-HO-DsBT 6.5-fold lower affinity for the serotonin 5-HT2A receptor compared to psilocin (4-HO-DMT).

History

4-HO-DBT was first described in the scientific literature by David Repke and colleagues in 1977. It was subsequently described in further detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I have Known and Loved).

References

References

1. "4-HO-DBT".
2. (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology.
3. (1977). "Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl] ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols". Journal of Heterocyclic Chemistry.