Ethocybin

Ethocybin (code name CEY-19), also known as 4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET), is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family.^[1]

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	4–6 hours[1]
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
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Pharmacology

Ethocybin may be dephosphorylated in vivo to 4-HO-DET (ethocin), analogously to how psilocybin is metabolized to psilocin.^[2] This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. 4-HO-DET acts as a partial agonist at the 5-HT_2A serotonin receptor.^[3][4]

History

Albert Hofmann was the first to produce ethocybin, soon after his discovery of psilocin and psilocybin.^[5][6] It was first described by 1963.^[5][6] The drug was known under the code name CEY-19.^[6]

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.

Research

Ethocybin has been studied as a treatment for several disorders since the early 1960s, and numerous papers are devoted to this material.^{[citation needed]} Its short-lived action was considered a virtue. A 2010 study found that ethocybin helped with bipolar affective disorder.^{[citation needed]}