Chemistry:Ethocybin

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Ethocybin also known as 4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19, is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin.[1] It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT).[1][2] The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.[3][4]

Use and effects

Interactions

Pharmacology

Ethocybin may be dephosphorylated in vivo to 4-HO-DET (ethocin), analogously to how psilocybin (4-PO-DMT) is metabolized to psilocin (4-HO-DMT).[5] This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. 4-HO-DET acts as a partial agonist of the serotonin 5-HT2A receptor.[6][7]

Chemistry

Analogues

Analogues of ethocybin include 4-HO-DET (ethocin), 4-AcO-DET (ethacetin), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), baeocystin (4-PO-NMT), and aeruginascin (4-PO-TMT), among others.

History

Albert Hofmann and colleagues working at Sandoz were the first to synthesize and describe ethocybin (CEY-19) along with 4-HO-DET (CZ-74), which shortly followed his discovery of psilocin and psilocybin.[3][4] They first described the drug in a patent by 1963.[3][4] Along with 4-HO-DET, ethocybin was one of the earliest structurally modified or synthetic psychedelic tryptamines to be developed.[8][9]

Society and culture

Canada

Ethocybin is not an explicitly nor implicitly controlled substance in Canada as of 2025.[10]

United States

Ethocybin is not an explicitly controlled substance in the United States.[11] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

Research

Ethocybin, under the code name CEY-19 and along with 4-HO-DET (CZ-74), has been studied in psychedelic-assisted psychotherapy.[12][1][4]

See also

References

  1. ↑ 1.0 1.1 1.2 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. 
  2. ↑ "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci 4 (2): 533–542. April 2021. doi:10.1021/acsptsci.0c00176. PMID 33860183. 
  3. ↑ 3.0 3.1 3.2 US patent 3075992, Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29 
  4. ↑ 4.0 4.1 4.2 4.3 "Two new short-acting hallucinogens of the psilocybin group". Neuropsychopharmacology 4: 471–474. 1965. https://bibliography.maps.org/resources/download/19910. 
  5. ↑ "EMCDDA | Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)". https://www.emcdda.europa.eu/publications/drug-profiles/mushrooms. 
  6. ↑ "EMCDDA | Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)". https://www.emcdda.europa.eu/publications/drug-profiles/mushrooms. 
  7. ↑ "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. April 2023. doi:10.1124/jpet.122.001454. PMID 36669875. 
  8. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named Nichols2018
  9. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named RossFrancoReiff2021
  10. ↑ "Controlled Drugs and Substances Act". 5 December 2025. https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  11. ↑ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026, https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf 
  12. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named Passie2022



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