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).^[1] It is taken orally.^[1]

4-HO-DBT

Clinical data
Other names	4-OH-DBT; 4-Hydroxy-N,N-dibutyltryptamine
Routes of administration	Oral[1]
Drug class	Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name N-butyl-N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number	63065-89-4 N
PubChem CID	21854224
ChemSpider	10579818 Y
UNII	R3EY4G4BLQ
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.435 g·mol−1
3D model (JSmol)	Interactive image
Melting point	74 to 75 °C (165 to 167 °F)
SMILES CCCCN(CCCC)CCc2c[nH]c1cccc(O)c12
InChI 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 Y Key:BDOJPNJIBDXWQQ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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

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

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

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

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

• Substituted tryptamine