Ethocybin

From Wikipedia, the free encyclopedia

This article may require cleanup to meet Wikipedia's quality standards.
Please discuss this issue on the talk page or replace this tag with a more specific message.
This article has been tagged since October 2006.

Ethocybin

General
Systematic name	4-Phosphoryloxy-N,N- diethyl-tryptamine
Molecular formula	C₁₄H₂₁N₂O₄P
SMILES	{{{1}}}
Molar mass	311.2939096 g/mol
CAS number	??&rn=1 ?? ??
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Ethocybin (CEY-39; 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.

1 Chemistry
2 Pharmacology
3 Medicine
4 Effects
5 Pharmacology
6 Legality
7 See also
8 References

[edit] Chemistry

As with psilocybin and psilocin, ethocybin is may be 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.

[edit] Pharmacology

As with psilocybin, ethocybin is rapidly dephosphorylated in the body to psilocin 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).

[edit] Medicine

Ethocybin has been studied as a treatment for several disorders since the early 1960s, and numerous papers are devoted to this material. It's short-lived action was considered a virtue.

[edit] Effects

Ethocybin is absorbed through the lining of the mouth and stomach. Effects begin 20-45 minutes after ingestion, and last from 2-4 hours depending on dose, species, and individual metabolism. The effects are somewhat shorter compared to psilocybin.

[edit] Pharmacology

Ethocybin is probably metabolized mostly in the liver where it becomes ethocin, but is also broken down by the enzyme monoamine oxidase.

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.