4-HO-DALT

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4-HO-DALT
4-HO-DALT structure.png
Clinical data
Other names4-Hydroxy-N,N-diallyltryptamine; 4-Hydroxy-DALT; 4-OH-DALT; Daltocin; Dalocin
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 3-[2-[bis(prop-2-enyl)amino]ethyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C16H20N2O
Molar mass 256.349 g·mol−1
3D model (JSmol)
  • C=CCN(CCC1=CNC2=C1C(=CC=C2)O)CC=C
  • InChI=1S/C16H20N2O/c1-3-9-18(10-4-2)11-8-13-12-17-14-6-5-7-15(19)16(13)14/h3-7,12,17,19H,1-2,8-11H2
  • Key:JVIWQWJXRKVJTA-UHFFFAOYSA-N

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]

Contents

Use and effects

4-HO-DALT was not included or mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). [4] However, in a subsequently released entry, it was briefly mentioned. [4] 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. [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. [4] Subsequently, it was further described in 2017 and thereafter. [3] [1] [2]

See also

References

  1. 1 2 3 4 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.
  2. 1 2 3 4 Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, et al. (April 2023). "Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice". ACS Pharmacology & Translational Science. 6 (4): 567–577. doi:10.1021/acsptsci.2c00222. PMC   10111620 . PMID   37082754.
  3. 1 2 Brandt SD, Kavanagh PV, Dowling G, Talbot B, Westphal F, Meyer MR, et al. (January 2017). "Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives". Drug Testing and Analysis. 9 (1): 115–126. doi:10.1002/dta.1974. PMC   5412731 . PMID   27100373.
  4. 1 2 3 4 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. 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."
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