Chemistry:DALT

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Diallyltryptamine (DALT), also known as N,N-diallyltryptamine, is a tryptamine derivative which has been identified as a designer drug.[1][2]

Use and effects

According to Alexander Shulgin in TiHKAL, the dosage of DALT is >40 mg orally and its duration is unknown.[3] Its effects have not been described.[3] 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.[3][4][5]

Interactions

Pharmacology

Pharmacodynamics

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 ND
MOR, DOR >10,000
KOR 2,477
SERT 150 (Ki)
NET 1,121 (Ki)
DAT 1,406 (Ki)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Refs:[6][7][8][9]

The receptor interactions of DALT have been studied.[6][7][8][9] The drug produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents.[10]

Chemistry

DALT has been used as an intermediate in the preparation of radiolabeled diethyltryptamine (DET).[11]

Synthesis

The chemical synthesis of DALT has been described.[3]

Analogues

Analogues of DALT include 4-HO-DALT, 4-AcO-DALT, 5-MeO-DALT, and methylallyltryptamine (MALT), among others.[3]

History

DALT was first described in the scientific literature by Stephen Szara and colleagues by 1962.[4][5]

See also

References

  1. ↑ "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". Analytical and Bioanalytical Chemistry 407 (25): 7831–42. October 2015. doi:10.1007/s00216-015-8955-0. PMID 26297461. http://researchonline.ljmu.ac.uk/id/eprint/3406/1/ABC-01148-2015.R1.pdf. 
  2. ↑ "n, and LC-HR-MS/MS". Analytical and Bioanalytical Chemistry 409 (6): 1681–1695. February 2017. doi:10.1007/s00216-016-0117-5. PMID 27933361. http://researchonline.ljmu.ac.uk/id/eprint/4885/1/ABC_5F_7Me_5%2C6MD-DALT_accepted.pdf. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. http://www.erowid.org/library/books_online/tihkal/tihkal.shtml. 
  4. ↑ 4.0 4.1 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "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." 
  5. ↑ 5.0 5.1 "The 6-Hydroxylation of Tryptamine Derivatives: A Way of Producing Psychoactive Metabolites". Annals of the New York Academy of Sciences 96 (1): 134–141. 1962. doi:10.1111/j.1749-6632.1962.tb50108.x. Bibcode: 1962NYASA..96..134S. "The dipropyl and diallyl derivatives have similar hallucinogenic activity in man, as we found recently.". 
  6. ↑ 6.0 6.1 "Kᵢ Database". 28 March 2025. 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=. 
  7. ↑ 7.0 7.1 "BindingDB BDBM50140058 CHEMBL3752576". Bioorganic & Medicinal Chemistry Letters 26 (3): 959–964. 2016. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781. https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50140058. Retrieved 28 March 2025. 
  8. ↑ 8.0 8.1 "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines". Bioorganic & Medicinal Chemistry Letters 26 (3): 959–964. February 2016. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781. 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. 
  9. ↑ 9.0 9.1 "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs". Neuropharmacology 142: 231–239. November 2018. doi:10.1016/j.neuropharm.2018.02.028. PMID 29499272. PMC 6230509. 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. 
  10. ↑ "Effect of Hallucinogens on Unconditioned Behavior". Behavioral Neurobiology of Psychedelic Drugs. Curr Top Behav Neurosci. 36. 2018. pp. 159–199. doi:10.1007/7854_2016_466. ISBN 978-3-662-55878-2. "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)." 
  11. ↑ "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. 2008. doi:10.1002/jlcr.1557. 

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