4-HO-DBT
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). It is taken orally.
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| Other names | 4-OH-DBT; 4-Hydroxy-N,N-dibutyltryptamine |
| Routes of administration | Oral[1] |
| Drug class | Serotonergic psychedelic; Hallucinogen |
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| Formula | C18H28N2O |
| Molar mass | 288.435 g·mol−1 |
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| Melting point | 74 to 75 °C (165 to 167 °F) |
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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
[edit]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.[citation needed]
Interactions
[edit]Chemistry
[edit]Properties
[edit]4-HO-DBT is found either as its crystalline hydrochloride salt or as an oily or crystalline base.
Synthesis
[edit]The chemical synthesis of 4-HO-DBT has been described.[1]
Isomers
[edit]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]
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4-HO-DBT -
4-HO-DiBT -
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4-HO-DtBT
History
[edit]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
[edit]References
[edit]- ^ a b c d e f g Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "4-HO-DBT".
- ^ a b McKenna DJ, Repke DB, Lo L, Peroutka SJ (March 1990). "Differential interactions of indolealkylamines with 5-hydroxytryptamine receptor subtypes". Neuropharmacology. 29 (3): 193–198. doi:10.1016/0028-3908(90)90001-8. PMID 2139186.
- ^ Repke DB, Ferguson WJ, Bates DK (1977). "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. doi:10.1002/jhet.5570140113. ISSN 0022-152X. Retrieved 9 October 2025.