DALT

Last updated

DALT
DALT-structure.png
Clinical data
Other namesN,N-Diallyltryptamine; DALT; DAT
Routes of
administration 		Oral, intramuscular injection [1]
Drug class Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US: Analogue to a Schedule I/II drug(possibly)
  • UN:Unscheduled but not approved for human consumption.
  • in theory could be covered under similar analogue bills in other countries but this is not confirmed.
Identifiers
  • N-Allyl-N-[2-(1H-indol-3-yl)ethyl]prop-2-en-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H20N2
Molar mass 240.350 g·mol−1
3D model (JSmol)
  • C=CCN(CC=C)CCc2c[nH]c1ccccc12
  • InChI=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 Yes check.svgY
  • Key:LQEATNFJCMVKAC-UHFFFAOYSA-N Yes check.svgY
   (verify)

N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance. [2] [3] It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine. [4]

Contents

Use and effects

According to Alexander Shulgin in TiHKAL , the dosage of DALT is >40 mg orally and its duration is unknown. [1] Its effects have not been described. [1] 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 hours. [1] [5] [6]

Pharmacology

DALT activities
Target Affinity (Ki, nM)
5-HT1A 100
5-HT1B >10,000
5-HT1D 689
5-HT1E 378
5-HT1F ND
5-HT2A 701
5-HT2B 61
5-HT2C 385
5-HT3 >10,000
5-HT4 ND
5-HT5A >10,000
5-HT6 1,718
5-HT7 >10,000
α1A 1,663
α1B 1,369
α1D >10,000
α2A 124
α2B 305
α2C 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 ND
σ1 101 (rat)
σ2 356 (rat)
TAAR1 Tooltip Trace amine-associated receptor 1ND
MOR Tooltip μ-Opioid receptor, DOR Tooltip δ-Opioid receptor>10,000
KOR Tooltip κ-Opioid receptor2,477
SERT Tooltip Serotonin transporter150 (Ki)
NET Tooltip Norepinephrine transporter1,121 (Ki)
DAT Tooltip Dopamine transporter1,406 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs: [7] [8] [9] [10]

The receptor interactions of DALT have been studied. [7] [8] [9] [10] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [11]

History

DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962. [5] [6]

See also

References

  1. 1 2 3 4 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. ↑ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "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" (PDF). Analytical and Bioanalytical Chemistry. 407 (25): 7831–42. doi:10.1007/s00216-015-8955-0. PMID   26297461. S2CID   26086597.
  3. ↑ Michely JA, Brandt SD, Meyer MR, Maurer HH (February 2017). "n, and LC-HR-MS/MS" (PDF). Analytical and Bioanalytical Chemistry. 409 (6): 1681–1695. doi:10.1007/s00216-016-0117-5. PMID   27933361. S2CID   206920201.
  4. ↑ Brandt SD, Tirunarayanapuram SS, Freeman S, Dempster N, Barker SA, Daley PF, et al. (2008). "Microwave-accelerated synthesis of psychoactive deuterated N,N-dialkylated-[α,α,β,β-d4]-tryptamines". Journal of Labelled Compounds and Radiopharmaceuticals. 51 (14): 423–429. doi:10.1002/jlcr.1557.
  5. 1 2 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. 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.
  6. 1 2 Szara S, Hearst E (1962). "The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences. 96 (1): 134–141. Bibcode:1962NYASA..96..134S. doi:10.1111/j.1749-6632.1962.tb50108.x. The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.
  7. 1 2 "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.
  8. 1 2 Liu T (2016). "BindingDB BDBM50140058 CHEMBL3752576". Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID   26739781 . Retrieved 28 March 2025.
  9. 1 2 Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines" (PDF). Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID   26739781.
  10. 1 2 Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs" (PDF). Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC   6230509 . PMID   29499272.
  11. ↑ Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. Vol. 36. pp. 159–199. doi:10.1007/7854_2016_466. ISBN   978-3-662-55878-2. PMC   5787039 . PMID   28224459. 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).
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