4-HO-DET

Last updated
4-HO-DET
4-HO-DET.svg
4-HO-DET-3d-sticks.png
Clinical data
Other names4-OH-DET; 4-Hydroxy-N,N-diethyltryptamine; Ethocin; CZ-74; CZ74
Routes of
administration 		Oral [1]
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action 4–6 hours [1]
Identifiers
  • 3-(2-Diethylaminoethyl)-1H-indol-4-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H20N2O
Molar mass 232.327 g·mol−1
3D model (JSmol)
Melting point 104 to 106 °C (219 to 223 °F)
  • CCN(CC)CCc1c[nH]c2cccc(O)c12
  • InChI=1S/C14H20N2O/c1-3-16(4-2)9-8-11-10-15-12-6-5-7-13(17)14(11)12/h5-7,10,15,17H,3-4,8-9H2,1-2H3 Yes check.svgY
  • Key:OHHYMKDBKJPILO-UHFFFAOYSA-N Yes check.svgY
   (verify)

4-HO-DET, also known as 4-hydroxy-N,N-diethyltryptamine as well as ethocin or CZ-74, is a psychedelic drug of the tryptamine family. [1] It is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT. [1] [2]

Contents

Use

TiHKAL reports moderate effects at 10 to 25 mg ingested orally. [1] [3]

Effects

4-HO-DET produces psychedelic effects similar to psilocybin. [1] Its duration is 4 to 6 hours. [1]

Interactions

Pharmacology

The pharmacology of 4-HO-DET has been studied. [4]

Chemistry

Analogues

4-HO-DET is the N,N-diethyl analog of psilocin. The acetic acid ester of 4-HO-DET is known as 4-AcO-DET and the phosphoric acid ester of 4-HO-DET is known as 4-phosphoryloxy-DET, CEY-19, or ethocybin. These compounds may likely be prodrugs of 4-HO-DET as has been shown with the acetate and phosphate esters of other methylated tryptamines such as psilocin. [5]

History

4-HO-DET received the lab code CZ-74 in the late 1950s by the inventors of the substance, Albert Hofmann and Franz Troxler. The substance was used together with its phosphoryloxy-analog ethocybin in human clinical trials in the 1960s by the German researchers Hanscarl Leuner and G. Baer. [6] It was later explored by Alexander Shulgin in his 1997 book TiHKAL . [7]

Society and culture

Finland

Scheduled in the "government decree on psychoactive substances banned from the consumer market". [8]

Sweden

Sveriges riksdags health ministry Statens folkhälsoinstitut classified 4-HO-DET as "health hazard" under the act Lagen om förbud mot vissa hälsofarliga varor (translated Act on the Prohibition of Certain Goods Dangerous to Health) as of Nov 1, 2005, in their regulation SFS 2005:733 listed as 4-hydroxi-N,N-diethyltryptamin (4-HO-DET), making it illegal to sell or possess. [9]

United States

4-HO-DET is unscheduled in the United States, but purchase, sale, or possession for human consumption could be prosecuted under the Federal Analogue Act. [10]

References

  1. 1 2 3 4 5 6 7 Shulgin A, Shulgin A (September 1997). "#16 4-HO-DET". Isomer Design. Transform Press. Retrieved 28 November 2023.
  2. ↑ Greene SL (2021). "Tryptamines". In Dargan PI, Wood DM (eds.). Novel Psychoactive Substances: Classification, Pharmacology and Toxicology (Second ed.). London, United Kingdom: Academic Press. p. 499. ISBN   978-0-12-819030-2.
  3. ↑ Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152. Table 4 Human potency data for selected hallucinogens. [...]
  4. ↑ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC   10029822 . PMID   36669875.
  5. ↑ Nichols DE (February 11, 1999). "Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" . Synthesis. 1999 (6): 935–938. doi:10.1055/s-1999-3490. S2CID   32044725.
  6. ↑ Leuner H, Baer G (1965). "Two new short-acting hallucinogens of the psilocybin group". Neuropsychopharmacology. 4: 471–474. Archived from the original on 2025-04-22.
  7. ↑ Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  8. ↑ finlex.fi
  9. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor;" [Ordinance amending the ordinance (1999: 58) on the prohibition of certain dangerous goods;](PDF). Svensk författningssamling (Swedish Code of Statutes) (in Swedish). 6 October 2005. Archived from the original (PDF) on 26 June 2021. Retrieved 6 September 2013.
  10. ↑ "21 U.S. Code § 841 - Prohibited acts A", LII / Legal Information Institute, retrieved 2016-08-02
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