Ethocybin

Ethocybin

Clinical data
ATC code	none
Legal status
Legal status	DE: Anlage I (Controlled) UK: Class A
Identifiers
IUPAC name Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
Synonyms	4-Phosphoryloxy-N,N-diethyltryptamine; CEY-39; 4-phosphoryloxy-DET; 4-PO-DET
CAS Number	60480-02-6 Y
ChemSpider	21106438 Y
Chemical and physical data
Formula	C14H21N2O4P
Molar mass	312.30 g/mol
3D model (Jmol)	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

Ethocybin (CEY-19; 4-phosphoryloxy-DET; 4-PO-DET) is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Effects of ethocybin are comparable to those of a shorter LSD or psilocybin, although intensity and duration vary depending on dosage, individual physiology, and set and setting.

As with psilocybin, miprocybin and metocybin, ethocybin is a prodrug that is converted into the pharmacologically active compound ethocin in the body by dephosphorylation. This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body.

Albert Hofmann was the first to produce this chemical, soon after his discovery of psilocin and psilocybin. It was sold under the code name CEY-39.

As with psilocybin, ethocybin is rapidly dephosphorylated in the body to 4-HO-DET which then acts as a partial agonist at the 5-HT_2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT).

Ethocybin has been studied as a treatment for several disorders since the early 1960s, and numerous papers are devoted to this material. Its short-lived action was considered a virtue. A 2010 Study showed that Ethocybin helped with bipolar personality disorder.