Chemistry:4-HO-DALT

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4-HO-DALT, also known as 4-hydroxy-N,N-diallyltryptamine or as daltocin, is a serotonin receptor agonist and serotonergic psychedelic of the tryptamine and 4-hydroxytryptamine families.[1][2][3] It has been encountered as a novel designer drug.[4]

Use and effects

4-HO-DALT was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[5] However, in a subsequently released entry, it was briefly mentioned.[5] He does not appear to have synthesized or tested it and its properties were not described, but Shulgin hypothesized that the drug, in its prodrug form 4-AcO-DALT, would have a very rapid onset of action.[5] Subsequently, 4-HO-DALT has emerged as a novel designer drug.[4] It is said to produce hallucinogenic effects similar to those of 4-HO-DiPT and 4-HO-DPT.[4]

Interactions

Pharmacology

Pharmacodynamics

4-HO-DALT binds to many of the serotonin receptors, including the serotonin 5-HT2A receptor, as well as other targets.[1][2] The drug acts as a potent full agonist of the serotonin 5-HT2A and 5-HT2B receptors, whereas it showed 60-fold lower potency as an agonist of the serotonin 5-HT2C receptor compared to the serotonin 5-HT2A receptor.[2] It produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[1]

Chemistry

Analogues

Analogues of 4-HO-DALT include diallyltryptamine (DALT), 4-AcO-DALT, 5-MeO-DALT, 4-HO-MALT, psilocin (4-HO-DMT), 4-HO-DET (ethocin), 4-HO-DPT, and 4-HO-DiPT, among others.

History

4-HO-DALT was first described by Alexander Shulgin in a follow-up entry of TiHKAL (Tryptamines I Have Known and Loved) in 2004.[5] Subsequently, it was further described in 2017 and thereafter.[3][1][2] The drug was encountered online as a novel designer drug by 2014.[4] In 2023, it was found to be sold as an analytical standard.[4]

Society and culture

Canada

4-HO-DALT is not a controlled substance in Canada as of 2025.[6]

See also

References

  1. ↑ 1.0 1.1 1.2 1.3 "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://shulginresearch.net/wp-content/uploads/2021/07/Receptor-binding-profiles-and-behavioral-pharmacology-of-DALT-analogs.-Klein.-Neuropharmacology-142-231-239-2018.pdf. 
  2. ↑ 2.0 2.1 2.2 2.3 "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science 6 (4): 567–577. April 2023. doi:10.1021/acsptsci.2c00222. PMID 37082754. 
  3. ↑ 3.0 3.1 "Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives". Drug Testing and Analysis 9 (1): 115–126. January 2017. doi:10.1002/dta.1974. PMID 27100373. 
  4. ↑ 4.0 4.1 4.2 4.3 4.4 "4-HO-DALT (4-hydroxy DALT)" (in ru). https://aipsin.com/newsubstance/1106/. 
  5. ↑ 5.0 5.1 5.2 5.3 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.  https://isomerdesign.com/pihkal/read/tk/56#5530 "Another direction possible for modifying the structure would be to relocate the oxygen in indole ring over to the 4-position. 4-Methoxytryptamine is commercially available, and it should be directly substitutable for the 5-methoxytryptamine used in this synthetic process giving rise to 4-MeO-DALT. Yet further out, what about starting the 4-benzyloxytryptamine and walking the same path? The product could be easily stripped of the benzyl ether by the usual catalytic hydrogenation, giving rise to the diallyl analogue of psilocin, 4-HO-DALT. I would wager a ten dollar bet that the acetate ester of this material, 4-AcO-DALT would be in the brain within minutes of swallowing the pill."
  6. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 



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