4-HO-DBT

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4-HO-DBT
4-HO-DBT.svg
4-HO-DBT 3D.png
Clinical data
Other names4-OH-DBT; 4-Hydroxy-N,N-dibutyltryptamine
Routes of
administration 		Oral [1]
Drug class Serotonergic 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
Formula C18H28N2O
Molar mass 288.435 g·mol−1
3D model (JSmol)
Melting point 74 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 Yes check.svgY
  • Key:BDOJPNJIBDXWQQ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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]

Contents

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.[ citation needed ]

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]

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 2 3 4 5 6 7 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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