Psilocin

Psilocin

File:Psilocin Structural Formulae V.1.svg
File:Psilocin-3d-CPK.png
Systematic (IUPAC) name
3-[2-(Dimethylamino)ethyl]-4-indolol
Clinical data
Routes of administration	Oral, IV
Legal status
Legal status	AU: S9 (Prohibited) CA: Schedule III UK: Class A US: Schedule I
Pharmacokinetic data
Metabolism	Liver
Biological half-life	2-3 hours
Excretion	Kidneys/Urine
Identifiers
CAS Number	520-53-6
ATC code	none
PubChem	CID 4980
ChemSpider	4807
Chemical data
Formula	C12H16N2O
Molar mass	204.27 g/mol[[]]
Physical data
Melting point	173 to 176 °C (343 to 349 °F)

Psilocin (4-hydroxy-dimethyltryptamine, 4-HO-DMT), an aromatic compound, sometimes also (mis)spelled psilocine, psilocyn, or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind altering effects of psilocin are highly variable and subjective. The effects typically last anywhere from 3 to 8 hours depending on certain variables (such as metabolism, food interaction), however the effects can seem to last much longer due to psilocin's ability to distort the perception of time.

Chemistry

Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). Another synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

Psilocin is relatively unstable in solution due to its phenolic hydroxy (-OH) group. In the presence of oxygen it readily forms bluish and dark black degradation products. Similar products are also formed under acidic conditions in the presence of oxygen and Fe³⁺ ions (Keller's reagent).

Structural analogs

Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N¹-methylpsilocin is a functionally 5-HT_2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known.

Pharmacology

Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or some species of psychedelic mushrooms.

Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT_2A, 5HT_2C and 5HT_1A agonist. Psilocin is structurally similar to serotonin (5-HT), differing only by the hydroxyl group being on the 4-position rather than the 5 and the dimethyl groups on the nitrogen. Its effects are thought to come from its partial agonist activity at 5-HT_2A serotonin receptors in the prefrontal cortex.

Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the noradrenergic system at very high dosages.

Psilocin's physiological half-life ranges from 2 to 3 hours.

See psilocybin for more details

Behavioral and non-behavioral effects

File:Dried Cubensis.jpg

Dried psilocybe mushrooms. (Notice the characteristic blue bruising by the stems of the mushrooms.)

Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion can include but aren't limited to tachycardia, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synesthesia (eg. hearing colours and seeing sounds), increased body temperature, headache, sweating and chills, and nausea.

There is virtually no direct lethality associated with psilocin. There is virtually no withdrawal syndrome when chronic use of this drug is ceased. There is cross tolerance among psilocin, mescaline, and DMT.

See also

Psychedelic mushrooms Psilocybin Tryptamine O-Acetylpsilocin

Indole Psychedelic drug Psychoactive drug

External links

• The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
• The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
• 4-HO-DMT entry in TiHKAL
• Psilocin (4-HO-DMT) entry in TiHKAL • info

cs:Psilocin zh:脱磷酸裸盖菇素