Ethocybin

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]

Ethocybin

Clinical data
Other names	4-Phosphoryloxy-N,N-diethyltryptamine; CEY-19; 4-phosphoryloxy-DET; 4-PO-DET
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	DE: Anlage I (Authorized scientific use only) UK: Class A
Pharmacokinetic data
Duration of action	2–6 hours[1][2][3][4][5]
Identifiers
IUPAC name Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
CAS Number	60480-02-6 Y
PubChem CID	53633102
ChemSpider	21106438 Y
UNII	Z47K2YT973
CompTox Dashboard (EPA)	DTXSID80705541
Chemical and physical data
Formula	C14H21N2O4P
Molar mass	312.306 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)CCC2=CNC1=CC=CC(OP(O)(O)=O)=C12
InChI 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) Y Key:AAVKQQUBPHSCML-UHFFFAOYSA-N Y
(verify)

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-HT_2A receptor.^[10][11]

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

Legal status

United States

Ethocybin is not controlled in the United States, but possession or sale may be considered illegal under the Federal Analog Act.^{[citation needed]}

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

• Substituted tryptamine
• 4-HO-DET
• 4-AcO-DET
• Psilocybin (4-PO-DMT)