{{Short description|Chemical compound}} {{Drugbox | verifiedrevid = 450609898 | image = Dibutyltryptamine.svg | image_class = skin-invert-image | width = 200px | image2 = DBT 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | tradename = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | routes_of_administration = | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_AU = | legal_CA = | legal_DE = NpSG | legal_UK = Class A | legal_US = | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 15741-77-2 | PubChem = 27848 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 25911 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = QFE8WT8WCW | synonyms = ''N'',''N''-Dibutyltryptamine; DBT; ''N'',''N''-DBT
<!-- Chemical data --> | IUPAC_name = ''N''-butyl-''N''-[2-(1''H''-indol-3-yl)ethyl]butan-1-amine | C=18 | H=28 | N=2 | SMILES = CCCCN(CCCC)CCC1=CNC2=CC=CC=C21 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LZLJUZWFWYEQLY-UHFFFAOYSA-N
<!-- Physical data --> | melting_point = 186 | melting_high = 188 }}
'''Dibutyltryptamine''' ('''DBT'''), also known as '''''N'',''N''-dibutyltryptamine''' ('''''N'',''N''-DBT'''), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).<ref name="TiHKAL" />
==Use and effects== In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), Alexander Shulgin reported that a dose of 1{{nbsp}}mg/kg DBT by intramuscular injection was active, but less so than dimethyltryptamine (DMT) or diethyltryptamine (DET).<ref name="TiHKAL">{{CiteTiHKAL|name-list-style = vanc }}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1 | quote = The N,N-dibutyl derivative (4.11) showed a considerable decrease in activity, while increasing the chain length to N,N-dihexyl (4.12) abolished hallucinogenic effects in man (Szara, 1961b).}}</ref> This suggests that an active dose of DBT will be in the 100{{nbsp}}mg range.{{Citation needed|date=November 2025}} It has been sold as a "research chemical" and has been confirmed to be an active hallucinogen, although somewhat weaker than other similar tryptamine derivatives.{{Citation needed|date=April 2025}}
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Pharmacology== ===Pharmacodynamics=== DBT is a serotonin receptor agonist in the rat uterus and rat stomach strip, with similar potency as dimethyltryptamine (DMT).<ref name="BarlowKhan1959">{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 99–107 | date = March 1959 | pmid = 13651585 | pmc = 1481812 | doi = 10.1111/j.1476-5381.1959.tb00934.x | url = }}</ref> It produces the head-twitch response, a behavioral proxy of psychedelic effects, in mice.<ref name="pmid31230432">{{cite journal | vauthors = Abiero A, Ryu IS, Botanas CJ, Custodio RJ, Sayson LV, Kim M, Lee HJ, Kim HJ, Seo JW, Cho MC, Lee KW, Yoo SY, Jang CG, Lee YS, Cheong JH | display-authors = 6 | title = Four Novel Synthetic Tryptamine Analogs Induce Head-Twitch Responses and Increase 5-HTR2a in the Prefrontal Cortex in Mice | journal = Biomolecules & Therapeutics | pages = 83–91 | date = June 2019 | volume = 28 | pmid = 31230432 | doi = 10.4062/biomolther.2019.049 | pmc = 6939696 }}</ref>
==Chemistry== DBT is found either as its crystalline hydrochloride salt or as an oily or crystalline base.
===Synthesis=== The chemical synthesis of DBT has been described.<ref name="TiHKAL" />
===Isomers=== There are four symmetrical isomers of DBT which can be made, or ten isomers in total if unsymmetrical substitution is used.<ref name="TiHKAL" /> 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.<ref name="TiHKAL" />
{{Gallery | title = Chemical structures of DBT and its skeletal isomers | height = 150 | width = 150 | File:Dibutyltryptamine.svg | class1=skin-invert-image | DBT | File:DiBT structure.svg | class2=skin-invert-image | DiBT | File:DsBT structure.svg | class3=skin-invert-image | DsBT | File:DtBT structure.svg | class4=skin-invert-image | DtBT }}
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.{{Citation needed|date=November 2025}}
===Analogues=== Analogues of DBT include 4-HO-DBT, 4-HO-DsBT, 5-MeO-DBT, and dihexyltryptamine (DHT), among others.<ref name="TiHKAL" />
==History== DBT was first described in the scientific literature by 1959.<ref name="BarlowKhan1959">{{cite journal | vauthors = Barlow RB, Khan I | title = Actions of some analogues of tryptamine on the isolated rat uterus and on the isolated rat fundus strip preparations | journal = Br J Pharmacol Chemother | volume = 14 | issue = 1 | pages = 99–107 | date = March 1959 | pmid = 13651585 | pmc = 1481812 | doi = 10.1111/j.1476-5381.1959.tb00934.x | url = }}</ref>
==Society and culture== ===Legal status=== ====Canada==== DBT is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
====United States==== DBT is not an explicitly controlled substance in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.
==See also== * Substituted tryptamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5002 DBT - Isomer Design] * [https://www.erowid.org/library/books_online/tihkal/tihkal02.shtml DBT - TiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/tk/2 DBT - TiHKAL - Isomer Design]
{{Psychedelics}} {{Serotonin receptor modulators}} {{Tryptamines}}
Category:N,N-Dialkyltryptamines Category:Dibutylamino compounds Category:Psychedelic tryptamines Category:Serotonin receptor modulators Category:TiHKAL