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Ethocybin

Psychedelic drug

Psychedelic drug

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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. 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). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

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). 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.

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. They first described the drug in a patent by 1963. Along with 4-HO-DET, ethocybin was one of the earliest structurally modified or synthetic psychedelic tryptamines to be developed.

Society and culture

Canada

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

United States

Ethocybin is not an explicitly controlled substance in the United States. 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.

References

References

  1. (2018). "Chemistry and Structure-Activity Relationships of Psychedelics".
  2. Shulgin, Alexander T.. (1976). "Psychopharmacological Agents: Use, Misuse and Abuse". Academic Press.
  3. Passie, Torsten. (7 November 2022). "Handbook of Medical Hallucinogens". Guilford Publications.
  4. (9 March 2021). "Handbook of Medical Hallucinogens". Guilford Publications.
  5. {{CiteTiHKAL
  6. (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci.
  7. "EMCDDA {{!}} Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)".
  8. "EMCDDA {{!}} Hallucinogenic mushrooms profile (chemistry, effects, other names (magic mushrooms, shrooms…), origin, mode of use, other names, medical use, control status)".
  9. (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.
  10. "Esters of indoles".
  11. (1965). "Two new short-acting hallucinogens of the psilocybin group". Neuropsychopharmacology.
  12. (5 December 2025). "Controlled Drugs and Substances Act".
  13. (January 2026). "Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026)". U.S. [[Department of Justice]]: [[Drug Enforcement Administration]] (DEA): Diversion Control Division.
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5-ht1a-agonists 5-ht2a-agonists 5-ht2c-agonists alkaloids designer-prodrugs n,n-dialkyltryptamines diethylamino-compounds 4-phosphoryloxytryptamines psychedelic-assisted-therapy psychedelic-tryptamines tihkal
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