DALT

{{cs1 config|name-list-style=vanc|display-authors=6}} {{Short description|Chemical compound}} {{Drugbox | Watchedfields = changed | verifiedrevid = 451559106 | image = DALT structure.svg | image_class = skin-invert-image | width = 200px | image2 = DALT 3D.png | image_class2 = bg-transparent | width2 = 225px

<!-- Clinical data --> | tradename = | pregnancy_category = | routes_of_administration = Oral, intramuscular injection<ref name="TiHKAL" /> | class = Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =

<!-- Legal status --> | legal_DE = NpSG | legal_UK = Class A | legal_US = Analogue | legal_US_comment = (possibly) | legal_UN = Unscheduled but not approved for human consumption. | legal_status = in theory could be covered under similar analogue bills in other countries but this is not confirmed.

<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =

<!-- Identifiers --> | CAS_number = 60676-77-9 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 85113MO9BC | PubChem = 24839550 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 21250454 | synonyms = ''N'',''N''-Diallyltryptamine; DALT; DAT

<!-- Chemical data --> | IUPAC_name = ''N''-Allyl-''N''-[2-(1''H''-indol-3-yl)ethyl]prop-2-en-1-amine | C=16 | H=20 | N=2 | SMILES = C=CCN(CC=C)CCc2c[nH]c1ccccc12 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C16H20N2/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16/h3-8,13,17H,1-2,9-12H2 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = LQEATNFJCMVKAC-UHFFFAOYSA-N }}

'''Diallyltryptamine''' ('''DALT'''), also known as '''''N'',''N''-diallyltryptamine''', is a tryptamine derivative which has been identified as a designer drug.<ref name="pmid26297461">{{cite journal | vauthors = Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH | title = Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS | journal = Analytical and Bioanalytical Chemistry | volume = 407 | issue = 25 | pages = 7831–42 | date = October 2015 | pmid = 26297461 | doi = 10.1007/s00216-015-8955-0 | s2cid = 26086597 | url = http://researchonline.ljmu.ac.uk/id/eprint/3406/1/ABC-01148-2015.R1.pdf }}</ref><ref name="pmid27933361">{{cite journal | vauthors = Michely JA, Brandt SD, Meyer MR, Maurer HH | title = n, and LC-HR-MS/MS | journal = Analytical and Bioanalytical Chemistry | volume = 409 | issue = 6 | pages = 1681–1695 | date = February 2017 | pmid = 27933361 | doi = 10.1007/s00216-016-0117-5 | s2cid = 206920201 | url = http://researchonline.ljmu.ac.uk/id/eprint/4885/1/ABC_5F_7Me_5%2C6MD-DALT_accepted.pdf }}</ref>

==Use and effects== According to Alexander Shulgin in his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), the dose of DALT is greater than 40{{nbsp}}mg orally and its duration is unknown.<ref name="TiHKAL">{{CiteTiHKAL}}</ref> Its effects were not described.<ref name="TiHKAL" /> Per Stephen Szara and colleagues in much earlier publications however, DALT and other extended ''N'',''N''-dialkyltryptamines produce similar effects to dimethyltryptamine (DMT) but are longer-lasting, with durations of up to 3{{nbsp}}hours.<ref name="TiHKAL" /><ref name="BrimblecombePinder1975" /><ref name="SzaraHearst1962" />

==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}

==Pharmacology== ===Pharmacodynamics=== {| class="wikitable floatleft" style="font-size:small;" |+ {{Nowrap|DALT activities}} |- ! Target !! Affinity (K_i, nM) |- | 5-HT_1A || 100 |- | 5-HT_1B || >10,000 |- | 5-HT_1D || 689 |- | 5-HT_1E || 378 |- | 5-HT_1F || {{Abbr|ND|No data}} |- | 5-HT_2A || 701 |- | 5-HT_2B || 61 |- | 5-HT_2C || 385 |- | 5-HT₃ || >10,000 |- | 5-HT₄ || {{Abbr|ND|No data}} |- | 5-HT_5A || >10,000 |- | 5-HT₆ || 1,718 |- | 5-HT₇ || >10,000 |- | α_1A || 1,663 |- | α_1B || 1,369 |- | α_1D || >10,000 |- | α_2A || 124 |- | α_2B || 305 |- | α_2C || 901 |- | β₁–β₃ || >10,000 |- | D₁, D₂ || >10,000 |- | D₃ || 672 |- | D₄, D₅ || >10,000 |- | H₁ || 127 |- | H₂–H₄ || >10,000 |- | M₁–M₅ || >10,000 |- | I₁ || {{Abbr|ND|No data}} |- | σ₁ || 101 (rat) |- | σ₂ || 356 (rat) |- | {{Abbrlink|TAAR1|Trace amine-associated receptor 1}} || {{Abbr|ND|No data}} |- | {{Abbrlink|MOR|μ-Opioid receptor}}, {{Abbrlink|DOR|δ-Opioid receptor}} || >10,000 |- | {{Abbrlink|KOR|κ-Opioid receptor}} || 2,477 |- | {{Abbrlink|SERT|Serotonin transporter}} || 150 (K_i) |- | {{Abbrlink|NET|Norepinephrine transporter}} || 1,121 (K_i) |- | {{Abbrlink|DAT|Dopamine transporter}} || 1,406 (K_i) |- class="sortbottom" | colspan="2" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | '''Notes:''' The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. '''Refs:'''<ref name="PDSPKiDatabase">{{cite web | title=Kᵢ Database | website=PDSP | date=28 March 2025 | url=https://pdsp.unc.edu/kidb2/kidb/web/kis-results/index?KisResultsSearch%5Binput_receptors%5D=&KisResultsSearch%5Binput_sources%5D=&KisResultsSearch%5Binput_species%5D=&KisResultsSearch%5Binput_hot_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D=&KisResultsSearch%5Binput_test_ligands%5D%5B%5D=12644&KisResultsSearch%5Binput_citations%5D=&KisResultsSearch%5BsearchType%5D=&KisResultsSearch%5Bki_val_from%5D=&KisResultsSearch%5Bki_val_to%5D=&KisResultsSearch%5Bcustom_ki_val%5D= | access-date=28 March 2025}}</ref><ref name="BindingDB">{{cite journal | vauthors = Liu T | title=BindingDB BDBM50140058 CHEMBL3752576 | journal=Bioorganic & Medicinal Chemistry Letters | date=2016 | volume=26 | issue=3 | pages=959–964 | doi=10.1016/j.bmcl.2015.12.053 | pmid=26739781 | url=https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50140058 | access-date=28 March 2025}}</ref><ref name="CozziDaley2016">{{cite journal | vauthors = Cozzi NV, Daley PF | title = Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines | journal = Bioorganic & Medicinal Chemistry Letters | volume = 26 | issue = 3 | pages = 959–964 | date = February 2016 | pmid = 26739781 | doi = 10.1016/j.bmcl.2015.12.053 | url = https://shulginresearch.net/wp-content/uploads/2021/07/Receptor-binding-profiles-and-QSAR-of-some-5-substituted-DALTs.-Cozzi.-Biorg.-Med.-Chem.-Lett.-26-959-964-2016.pdf}}</ref><ref name="KleinCozziDaley2018">{{cite journal | vauthors = Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL | title = Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs | journal = Neuropharmacology | volume = 142 | issue = | pages = 231–239 | date = November 2018 | pmid = 29499272 | pmc = 6230509 | doi = 10.1016/j.neuropharm.2018.02.028 | url = https://crb.wisc.edu/wp-content/uploads/sites/141/2018/03/Receptor-binding-profiles-and-behavioral-pharmacology-of-DALT-analogs.-Klein.-Neuropharmacology-XXX-1-9-2018.pdf}}</ref> |}

The receptor interactions of DALT have been studied.<ref name="PDSPKiDatabase" /><ref name="BindingDB" /><ref name="CozziDaley2016" /><ref name="KleinCozziDaley2018" /> The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.<ref name="HalberstadtGeyer2018">{{cite book | vauthors = Halberstadt AL, Geyer MA | title = Behavioral Neurobiology of Psychedelic Drugs | chapter = Effect of Hallucinogens on Unconditioned Behavior | series = Curr Top Behav Neurosci | volume = 36 | pages = 159–199 | date = 2018 | pmid = 28224459 | pmc = 5787039 | doi = 10.1007/7854_2016_466 | isbn = 978-3-662-55878-2 | chapter-url = | quote = The HTR has also been observed in rodents treated with N-methyl-N-ethyltryptamine (MET), N,N-diethyltryptamine (DET), N,N-dipropyltryptamine (DPT), N,N-diisopropyltryptamine (DIPT), and N,N-diallyltryptamine (DALT) (Fantegrossi et al. 2008; Smith et al. 2014; Carbonaro et al. 2015; Halberstadt and Klein, unpublished observations).}}</ref>

==Chemistry== DALT has been used as an intermediate in the preparation of radiolabeled diethyltryptamine (DET).<ref>{{cite journal | vauthors = Brandt SD, Tirunarayanapuram SS, Freeman S, Dempster N, Barker SA, Daley PF, Cozzi NV, Martins CP | title = Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines | journal = Journal of Labelled Compounds and Radiopharmaceuticals | date = 2008 | volume = 51 | issue = 14 | pages = 423–429 | doi = 10.1002/jlcr.1557}}</ref>

===Synthesis=== The chemical synthesis of DALT has been described.<ref name="TiHKAL" />

===Analogues=== Analogues of DALT include 4-HO-DALT, 4-AcO-DALT, 5-MeO-DALT, methylallyltryptamine (MALT), propylallyltryptamine (PALT), and isopropylallyltryptamine (iPALT), among others.<ref name="TiHKAL" />

==History== DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962.<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 = Other N,N-dialkyltryptamines produce similar effects to DMT in man, though their persistence is somewhat greater, with hallucinations lasting for up to 3 hours (Szara and Hearst, 1962). These include the N,N-diethyl (DET, 4.8), N,N-dipropyl (4.9), and N,N-diallyl (4.10) compounds, none of which are found in nature.}}</ref><ref name="SzaraHearst1962">{{cite journal |doi=10.1111/j.1749-6632.1962.tb50108.x | quote = The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.| title = The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites| date = 1962| vauthors = Szara S, Hearst E | journal = Annals of the New York Academy of Sciences| volume = 96| issue = 1| pages = 134–141| bibcode = 1962NYASA..96..134S}}</ref>

==Society and culture== ===Legal status=== ====Canada==== DALT is not an explicitly nor implicitly controlled substance in Canada as of 2025.<ref name="CDSA2025">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | date=5 December 2025 | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=20 January 2026}}</ref>

====United States==== DALT 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/5372 DALT - Isomer Design] * [https://www.bluelight.org/xf/threads/713255 The Big & Dandy DALT (N,N-Diallyltryptamine) Thread - Bluelight] * [https://isomerdesign.com/pihkal/read/tk/57 DALT - TiHKAL - Isomer Design]

{{Psychedelics}} {{Serotonin receptor modulators}} {{Tryptamines}}

Category:Adrenergic receptor modulators Category:N,N-Dialkyltryptamines Category:Designer drugs Category:Diallylamino compounds Category:Dopamine receptor modulators Category:Entheogens Category:Psychedelic tryptamines Category:Serotonin receptor modulators Category:Sigma receptor modulators Category:TiHKAL