4-HO-DBT

4-Hydroxy-N,N-dibutyltryptamine (4-HO-DBT) is a psychedelic drug belonging to the tryptamine family. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base. 4-HO-DBT was first made by the chemist Alexander Shulgin and reported in his book TiHKAL. Shulgin reported a dosage of 20mg orally to be without effects. 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.

4-HO-DBT

Identifiers
IUPAC name N-Butyl-N-[2-(4-hydroxy-1H-indol-3-yl)ethyl]butan-1-amine
CAS Number	63065-89-4 N
ChemSpider	10579818 Y
Chemical and physical data
Formula	C18H28N2O
Molar mass	288.44 g/mol 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)

Several different isomers of this compound could be made (see DBT for a fuller discussion) but of these only the isobutyl isomer 4-HO-DIBT has been synthesised (mp 152-154 °C) and was also found to be inactive at a 20mg dose.