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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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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
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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

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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

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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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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] It was subsequently described in further detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I have Known and Loved).[1]

See also

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References

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