Chemistry:4-HO-DBT

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4-HO-DBT, also known as 4-hydroxy-N,N-dibutyltryptamine, is a psychedelic drug of the tryptamine family related to psilocin (4-HO-DMT).[1] It is taken orally.[1]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin reported that a 20 mg dose of 4-HO-DBT orally produced no effects.[1] 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.[1]

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 20 mg dose.[1] The serotonin receptor interactions of these isomers have been studied.[2] 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).[2]

History

4-HO-DBT was first described in the scientific literature by David Repke and colleagues in 1977.[3] It was subsequently described in further detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I have Known and Loved).[1]

See also

References

  1. 1.0 1.1 1.2 1.3 1.4 1.5 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml.  "4-HO-DBT". http://www.erowid.org/library/books_online/tihkal/tihkal15.shtml. 
  2. 2.0 2.1 "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology 29 (3): 193–198. March 1990. doi:10.1016/0028-3908(90)90001-8. PMID 2139186. 
  3. "Psilocin analogs. 1. Synthesis of 3‐[2‐(dialkylamino)ethyl ‐and 3‐[2‐(cycloalkylamino)ethyl] indol‐4‐ols"]. Journal of Heterocyclic Chemistry 14 (1): 71–74. 1977. doi:10.1002/jhet.5570140113. ISSN 0022-152X. https://onlinelibrary.wiley.com/doi/pdfdirect/10.1002/jhet.5570140113. Retrieved 9 October 2025.