DALT
{{cs1 config|name-list-format=vanc|display-authors=6}}
{{short description|Chemical compound}}
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 451559106
| image = DALT-structure.png
| width =
| tradename =
| pregnancy_category =
| routes_of_administration = Oral, intramuscular injection
| class = Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
| ATC_prefix = None
| ATC_suffix =
| 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.
| bioavailability =
| metabolism =
| elimination_half-life =
| excretion =
| 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
| IUPAC_name = N-Allyl-N-[2-(1H-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
}}
N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance.{{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 }}{{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 }} It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine.{{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}}
Use and effects
According to Alexander Shulgin in TiHKAL, the dosage of DALT is >40{{nbsp}}mg orally and its duration is unknown.{{CiteTiHKAL}} Its effects have not been described. According to Stephen Szara and colleagues 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.
Pharmacology
The receptor interactions of DALT have been studied. The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.{{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).}}
History
DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962.{{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.}}{{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}}
See also
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:Diallylamino compounds
Category:Dopamine receptor modulators
Category:Psychedelic tryptamines