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Psilocin
Systematic (IUPAC) name
4-Hydroxy-N,N-dimethyl-tryptamine
Identifiers
CAS number 520-53-6
ATC code none
PubChem 4980
ChemSpider 4807
Chemical data
Formula C12H16N2O 
Mol. mass 204.27 g/mol
SMILES eMolecules & PubChem
Physical data
Melt. point 173–176 °C (343–349 °F)
Pharmacokinetic data
Metabolism Liver
Half life 2-3 hours
Excretion Kidneys/Urine
Therapeutic considerations
Pregnancy cat.  ?
Legal status Prohibited (S9) (AU) Schedule III (CA) ? (UK) Schedule I (US)
Routes Oral, IV

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.[1] 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.

Contents

History

The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz Laboratories isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959, guided by self-administration.

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[2] as well as 4-SH-DMT[3]. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists.[4] 4-fluoro-N,N-dimethyltryptamine is known.[4]

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 5HT2A, 5HT2C and 5HT1A agonist. Psilocin is structurally similar to serotonin (5-HT)[5], 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 ability to mimic serotonin at 5-HT2A serotonin receptors in the brain.

Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the noradrenergic system at very high dosages.[6]

Psilocin's physiological half-life ranges from 2 to 3 hours.[6]

See psilocybin for more details

Behavioral and non-behavioral effects

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.[5]

There is virtually no direct lethality associated with psilocin.[5] There is virtually no withdrawal syndrome when chronic use of this drug is ceased.[5] There is cross tolerance among psilocin, mescaline, and DMT.[5]

See also

References

  1. ^ "Green list"
  2. ^ Chapman (1972) Perkin Trans. 1, 3011
  3. ^ Hofmann, Swiss 421,960 (1967); CA 68:95680n
  4. ^ a b Sard (2005): PMID 16061378
  5. ^ a b c d e Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
  6. ^ a b Psilocybin Investigator’s Brochure

External links








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