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4-HO-DALT
Clinical data
Other names4-Hydroxy-N,N-diallyltryptamine; 4-Hydroxy-DALT; 4-OH-DALT; Daltocin; Dalocin
Drug classSerotonin 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
FormulaC16H20N2O
Molar mass256.349ย gยทmolโˆ’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] It has been encountered as a novel designer drug.[4]

Use and effects

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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

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See also: Psychedelic drug ยงย Interactions, and Trip killer ยงย Serotonergic psychedelic antidotes

Pharmacology

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Pharmacodynamics

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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

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Analogues

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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

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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

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Canada

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

See also

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References

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  1. ^ a b c d 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: 231โ€“239. doi:10.1016/j.neuropharm.2018.02.028. PMCย 6230509. PMIDย 29499272.
  2. ^ a b c d Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, etย 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): 567โ€“577. doi:10.1021/acsptsci.2c00222. PMCย 10111620. PMIDย 37082754.
  3. ^ a b Brandt SD, Kavanagh PV, Dowling G, Talbot B, Westphal F, Meyer MR, etย al. (January 2017). "Analytical characterization of N,N-diallyltryptamine (DALT) and 16 ring-substituted derivatives". Drug Testing and Analysis. 9 (1): 115โ€“126. doi:10.1002/dta.1974. PMCย 5412731. PMIDย 27100373.
  4. ^ a b c d e "4-HO-DALT (4-hydroxy DALT)". ะะ˜ะŸะกะ˜ะ (in Russian). Retrieved 1 January 2026.
  5. ^ a b c d Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBNย 0-9630096-9-9. OCLCย 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."
  6. ^ "Controlled Drugs and Substances Act". Department of Justice Canada. Retrieved 19 January 2026.
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๐Ÿ“š Artikel Terkait di Wikipedia

DALT

Diallyltryptamine (DALT), also known as N,N-diallyltryptamine, is a tryptamine derivative which has been identified as a designer drug. According to Alexander

4-AcO-DALT

4-AcO-DALT, also known as 4-acetoxy-N,N-diallyltryptamine or as dalcetin, is a tryptamine derivative. It has been sold as a designer drug, but little

Dimethyltryptamine

(MiPT), diisopropyltryptamine (DiPT), methylallyltryptamine (MALT), diallyltryptamine (DALT), and pyr-T (N,N-tetramethylenetryptamine) and their derivatives

NB-5-MeO-DALT

known as 5-MeO-DALT BOC or as N1-tert-butoxycarbonyl-5-methoxy-N,N-diallyltryptamine, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families

5-MeO-DALT

the freebase form of 5-MeO-DALT. Analogues of 5-MeO-DALT include diallyltryptamine (DALT), 4-HO-DALT (daltocin), 4-AcO-DALT (dalcetin), NB-5-MeO-DALT

Propylallyltryptamine

family. It is an asymmetrical analogue of dipropyltryptamine (DPT) and diallyltryptamine (DALT). The drug is a non-selective serotonin receptor agonist, including

IPALT

It is an asymmetrical analogue of diisopropyltryptamine (DiPT) and diallyltryptamine (DALT). The drug is a non-selective serotonin receptor agonist, including

DiPT

dimethyltryptamine (DMT), diethyltryptamine (DET), dipropyltryptamine (DPT), diallyltryptamine (DALT), 5-MeO-DiPT, 4-HO-DiPT (iprocin), 5-HO-DiPT, 4-AcO-DiPT (ipracetin)