4-Hydroxy-''N,N''-dibutyltryptamine (4-HO-DBT) is a
psychedelic drug belonging to the
tryptamine
Tryptamine is an indolamine metabolite of the essential amino acid, tryptophan. The chemical structure is defined by an indole ─ a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the f ...
family. It is found either as its
crystalline
A crystal or crystalline solid is a solid material whose constituents (such as atoms, molecules, or ions) are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macros ...
hydrochloride
In chemistry, a hydrochloride is an acid salt resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (e.g. an amine). An alternative name is chlorhydrate, which comes from French. An archaic alternative n ...
salt
Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
or as an oily or crystalline
base. 4-HO-DBT was first made by the chemist
Alexander Shulgin and reported in his book
TiHKAL
''TIHKAL: The Continuation'' is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to '' PIHKAL: A Chemical Love Story'', ''TIHKAL'' is an acronym that stands for "Trypt ...
. Shulgin reported a dosage of 20 mg 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.
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 was synthesised by Shulgin (mp 152-154 °C) and was also found to be inactive at a 20 mg dose.
External links
TiHKAL entry4-HO-DBT entry in TiHKAL • info
Psychedelic tryptamines
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