Ethocybin

Psychedelic drug From Wikipedia, the free encyclopedia

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][6] The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.[7][8]

Other names4-Phosphoryloxy-N,N-diethyltryptamine; CEY-19; 4-phosphoryloxy-DET; 4-PO-DET
Routes of
administrationOral[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Quick facts Clinical data, Other names ...
Ethocybin
Skeletal formula of ethocybin
Ball-and-stick model of the ethocybin molecule as a zwitterion
Clinical data
Other names4-Phosphoryloxy-N,N-diethyltryptamine; CEY-19; 4-phosphoryloxy-DET; 4-PO-DET
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Duration of action2–6 hours[1][2][3][4][5]
Identifiers
  • Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21N2O4P
Molar mass312.306 g·mol−1
3D model (JSmol)
  • CCN(CC)CCC2=CNC1=CC=CC(OP(O)(O)=O)=C12
  • InChI=1S/C14H21N2O4P/c1-3-16(4-2)9-8-11-10-15-12-6-5-7-13(14(11)12)20-21(17,18)19/h5-7,10,15H,3-4,8-9H2,1-2H3,(H2,17,18,19) checkY
  • Key:AAVKQQUBPHSCML-UHFFFAOYSA-N checkY
  (verify)
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Use and effects

See also: 4-HO-DET § Use and effects

Interactions

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

Pharmacology

See also: 4-HO-DET § 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).[9] 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.[10][11]

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.[7][8] They first described the drug in a patent by 1963.[7][8] Along with 4-HO-DET, ethocybin was one of the earliest structurally modified or synthetic psychedelic tryptamines to be developed.[2][5]

Society and culture

Canada

Ethocybin is not an explicitly nor implicitly controlled substance in Canada as of 2025.[12]

United States

Ethocybin is not an explicitly controlled substance in the United States.[13] 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.[4][1][8]

See also

References

External links

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