Ethocybin
This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (March 2009) |
200px | |
Systematic (IUPAC) name | |
---|---|
Phosphoric acid mono-[3-(2-diethylamino-ethyl)-1H-indol-4-yl] ester | |
Identifiers | |
CAS Number | 60480-02-6 |
ATC code | none |
Synonyms | 4-Phosphoryloxy-N,N-diethyltryptamine; CEY-39; 4-phosphoryloxy-DET; 4-PO-DET |
Chemical data | |
Formula | C14H21N2O4P |
Molar mass | 312.30 g/mol[[Script error: No such module "String".]] |
Script error: No such module "collapsible list". |
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.[citation needed]
Chemistry
As with psilocybin and psilocin, ethocybin is a prodrug that is converted into the pharmacologically active compound ethocin in the body by dephosphorylation.[citation needed] 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.[1] It was sold under the code name CEY-39.
Pharmacology
As with psilocybin, ethocybin is rapidly dephosphorylated in the body to 4-HO-DET which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT).[citation needed]
Medicine
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.
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.[citation needed] The effects are somewhat shorter compared to psilocybin.
Pharmacology
Ethocybin is probably metabolized mostly in the liver where it becomes ethocin, but is also broken down by the enzyme monoamine oxidase.[citation needed]
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.
Legality
Ethocybin is not controlled in the USA, but possession or sale may be considered illegal under the Federal Analog Act.
References
- ↑ US patent 3075992, Hofmann, Albert; Troxler, Franz., "Esters of indoles", issued 1963-1-29
da:Psilocybin de:Psilocybin es:Psilocibina fr:Psilocybine io:Psilocibino it:Psilocibina hu:Pszilocibin nl:Psilocybine ja:シロシビン pl:Psylocybina pt:Psilocibina ru:Псилоцибин sk:Psilocybín fi:Psilosybiini sv:Psilocybin tr:Psilocybin
- Pages with script errors
- 2Fix
- Articles needing additional references from March 2009
- Articles with invalid date parameter in template
- All articles needing additional references
- Pages with broken file links
- Infobox drug tracked parameters
- Articles without EBI source
- Chemical pages without ChemSpiderID
- Chemical pages without DrugBank identifier
- Articles without KEGG source
- Articles without InChI source
- Articles without UNII source
- Drugs not assigned an ATC code
- Drugs with no legal status
- Articles containing unverified chemical infoboxes
- All articles with unsourced statements
- Articles with unsourced statements from March 2009
- Alkaloids
- Psychedelic tryptamines