''N,N''-Dibutyltryptamine (DBT) is a

psychedelic Psychedelics are a subclass of hallucinogenic drugs whose primary effect is to trigger non-ordinary states of consciousness (known as psychedelic experiences or "trips").Pollan, Michael (2018). ''How to Change Your Mind: What the New Science of ...

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

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, macrosc ...

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 na ...

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 quantitie ...

or as an oily or crystalline base. DBT was first synthesized by the chemist

Alexander Shulgin Alexander Theodore "Sasha" Shulgin (June 17, 1925 – June 2, 2014) was an American medicinal chemist, biochemist, organic chemist, pharmacologist, psychopharmacologist, and author. He is credited with introducing 3,4-methylenedioxymethamph ...

and reported in his book '' TiHKAL (Tryptamines i Have Known And Loved)''. Shulgin did not test DBT himself, but reports a human dosage of "1 mg/kg i.m." being active, but less so than

DMT ''N'',''N''-Dimethyltryptamine (DMT or ''N'',''N''-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including human beings, and which is both a derivative and a structural analog of tryptamine. It is used as a ...

or DET. This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "

research chemical Research chemicals are chemical substances used by scientists for medical and scientific research purposes. One characteristic of a research chemical is that it is for laboratory research use only; a research chemical is not intended for human o ...

" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a

head-twitch response The head-twitch response (HTR) is a rapid side-to-side head movement that occurs in mice and rats after the serotonin 5-HT2A receptor is activated. The prefrontal cortex may be the neuroanatomical locus mediating the HTR. Many serotonergic hallucino ...

in mice. There are four symmetrical isomers of DBT which can be made, or ten isomers in total if unsymmetrical substitution is used. Of these only the n-butyl analogue DBT is known to be active in humans; the isobutyl, sec-butyl, and tert-butyl isomers DIBT, DSBT and DTBT have never been tested and only DBT and DIBT were made by Shulgin. The unsymmetrical isomers BIBT, BSBT, BTBT, IBSBT, IBTBT and SBTBT are also possible but have never been made and no predictions have been made about their activity. Shulgin speculates that the s-butyl isomer DSBT may be more potent than the straight chain compound DBT, but that the more highly branched DIBT and DTBT would probably be inactive due to the bulk of the substituent group. As for longer chain compounds than butyl, they have not been made and would probably be inactive. Shulgin mentions that the monohexyl compound NHT is without activity. However the unsymmetrical compounds such as

methylbutyltryptamine MBT, or ''N''-methyl-''N''-butyltryptamine, is a lesser-known psychedelic drug. MBT was first synthesized by Alexander Shulgin. In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), the minimum dosage is listed as 250-400 mg, and the ...

show more promise, and a wide range of possible compounds could be made by pairing the various butyl isomers with methyl, ethyl, propyl, isopropyl or allyl groups

References

External links

TiHKAL entry
{{Tryptamines Psychedelic tryptamines

See also

References

External links