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4-HO-DBT

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4-HO-DBT
Clinical data
Other names4-OH-DBT; 4-Hydroxy-N,N-dibutyltryptamine
Routes of
administration		Oral[1]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N-butyl-N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC18H28N2O
Molar mass288.435 g·mol−1
3D model (JSmol)
Melting point74 to 75 °C (165 to 167 °F)
  • CCCCN(CCCC)CCc2c[nH]c1cccc(O)c12
  • InChI=1S/C18H28N2O/c1-3-5-11-20(12-6-4-2)13-10-15-14-19-16-8-7-9-17(21)18(15)16/h7-9,14,19,21H,3-6,10-13H2,1-2H3 checkY
  • Key:BDOJPNJIBDXWQQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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

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4-HO-DBT was first made by the chemist Alexander Shulgin and reported in his book TiHKAL.[1] Shulgin reported a dosage of 20 mg orally to be without 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

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Chemistry

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Properties

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

Synthesis

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The chemical synthesis of 4-HO-DBT has been described.[1]

Isomers

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See also: Dibutyltryptamine § 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]

History

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4-HO-DBT was first described in the scientific literature by David Repke and colleagues in 1977.[3]

See also

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References

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  1. ^ 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".
  2. ^ 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.
  3. ^ 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.
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