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]

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 in the literature by Alexander Shulgin in TiHKAL in 1997.[4] Subsequently, it was further described in 2017 and thereafter.[3][1][2]

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. ↑ 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.  "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."

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