N,N-Dibutyltryptamine (DBT) is a psychedelicdrug belonging to the tryptamine family. It is found either as its crystallinehydrochloridesalt or as an oily or crystalline base. DBT was first synthesized by the chemist Alexander Shulgin 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 or DET.[1] This suggests that an active dosage of DBT will be in the 100 mg range. This compound has been sold as a "research chemical" and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives. It produces a head-twitch response in mice.[2]
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 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
^Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, et al. (June 2019). "Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice". Biomolecules & Therapeutics. 28: 83–91. doi:10.4062/biomolther.2019.049. PMC6939696. PMID 31230432.
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TiHKAL entry
November 03, 2023
dibutyltryptamine, psychedelic, drug, belonging, tryptamine, family, found, either, crystalline, hydrochloride, salt, oily, crystalline, base, first, synthesized, chemist, alexander, shulgin, reported, book, tihkal, tryptamines, have, known, loved, shulgin, te. N N Dibutyltryptamine 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 DBT was first synthesized by the chemist Alexander Shulgin 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 or DET 1 This suggests that an active dosage of DBT will be in the 100 mg range This compound has been sold as a research chemical and has been confirmed to be an active hallucinogen although somewhat weaker than other similar tryptamine derivatives It produces a head twitch response in mice 2 DibutyltryptamineClinical dataATC codenoneLegal statusLegal statusDE NpSG Industrial and scientific use only UK Class AIdentifiersIUPAC name N butyl N 2 1H indol 3 yl ethyl butan 1 amineCAS Number15741 77 2 YPubChem CID27848ChemSpider25911 YUNIIQFE8WT8WCWCompTox Dashboard EPA DTXSID40166255Chemical and physical dataFormulaC 18H 28N 2Molar mass272 436 g mol 13D model JSmol Interactive imageMelting point186 to 188 C 367 to 370 F SMILES CCCCN CCCC CCC1 CNC2 CC CC C21InChI InChI 1S C18H28N2 c1 3 5 12 20 13 6 4 2 14 11 16 15 19 18 10 8 7 9 17 16 18 h7 10 15 19H 3 6 11 14H2 1 2H3 YKey LZLJUZWFWYEQLY UHFFFAOYSA N Y verify 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 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 groupsSee also edit4 HO DSBT 5 MeO DBTReferences edit Shulgin A Shulgin A September 1997 TiHKAL The Continuation Berkeley California Transform Press ISBN 0 9630096 9 9 OCLC 38503252 Abiero A Ryu IS Botanas CJ Custodio RJ Sayson LV Kim M et al June 2019 Four Novel Synthetic Tryptamine Analogs Induce Head Twitch Responses and Increase 5 HTR2a in the Prefrontal Cortex in Mice Biomolecules amp Therapeutics 28 83 91 doi 10 4062 biomolther 2019 049 PMC 6939696 PMID 31230432 External links editTiHKAL entry Retrieved from https en wikipedia org w index php title Dibutyltryptamine amp oldid 1086937323, wikipedia, wiki, book, books, library,
