Ethocybin

Ethocybin

Clinical data
Other names	4-Phosphoryloxy-N,N-diethyltryptamine; CEY-39; 4-phosphoryloxy-DET; 4-PO-DET
ATC code	none
Legal status
Legal status	DE: Anlage I (Authorized scientific use only) UK: Class A
Identifiers
IUPAC name Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester
CAS Number	60480-02-6 Y
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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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. Effects of ethocybin are comparable to those of a shorter LSD or psilocybin trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.

Effects

Effects begin 20 to 45 minutes after ingestion, and last from 2 to 4 hours depending on dose, species, and individual metabolism. The effects are somewhat shorter compared to psilocybin.

Mental and physical tolerance to psilocybin builds and dissipates quickly. Taking ethocybin more than three or four times in a week (especially two days in a row) can result in diminished effects. Tolerance dissipates after a few days, so frequent users often keep doses spaced five to seven days apart to avoid the effect.

Pharmacology

As with psilocybin, ethocybin is rapidly dephosphorylated in the body to 4-HO-DET (ethocin). This chemical reaction takes place under strongly acidic conditions or enzymatically by phosphatases in the body. Then, 4-HO-DET acts as a partial agonist at the 5-HT_2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT).

History

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.

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. Its short-lived action was considered a virtue. A 2010 study found that ethocybin helped with bipolar affective disorder.