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Psilocin



Psilocin
Systematic (IUPAC) name
4-Hydroxy-N,N-dimethyl-tryptamine
Identifiers
CAS number 520-53-6
ATC code  ?
PubChem 4980
Chemical data
Formula C12H16N2O 
Mol. mass 204.27 g/mol
SMILES search in eMolecules, PubChem
Physical data
Melt. point 173–176 °C (343–349 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism Liver
Half life 2-3 hours
Excretion Kidneys/Urine
Therapeutic considerations
Pregnancy cat.

?

Legal status

Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US)

Routes Oral, IV

Psilocin (4-HO-DMT) 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]

Contents

History

The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz 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 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, FeCl3 / MeOH / HCl).

Pharmacology

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

Psilocybin is rapidly dephosphorylated in the body to psilocin which acts as a 5HT2A, 5HT2C and 5HT1A agonist. It's effects are thought to come from it's ability to mimic serotonin (5-HT) and thereby activate serotonin receptors in the brain.

Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the norephenephrine system at very high dosages.[2]

Psilocin half-life ranges from 2 to 3 hours.[3]

See psilocybin for more details.

See also

References

  1. ^ "Green list"
  2. ^ Psilocybin Investigator’s Brochure
  3. ^ Psilocybin Investigator’s Brochure
v • d • e
Drugs from TiHKAL

AL-LAD • DBT • DET • DiPT • 5-MeO-α-MT • DMT • 2,α-DMT • α,N-DMT • DPT • EiPT • α-ET • ETH-LAD • Harmaline • Harmine • 4-HO-DBT • 4-HO-DET • 4-HO-DiPT • 4-HO-DMT • 5-HO-DMT • 4-HO-DPT • 4-HO-MET • 4-HO-MiPT • 4-HO-MPT • 4-HO-pyr-T • Ibogaine • LSD • MBT • 4,5-MDO-DiPT • 5,6-MDO-DiPT • 4,5-MDO-DMT • 5,6-MDO-DMT • 5,6-MDO-MiPT • 2-Me-DET • 2-Me-DMT • Melatonin • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 4-MeO-MiPT • 5-MeO-MiPT • 5,6-MeO-MiPT • 5-MeO-NMT • 5-MeO-pyr-T • 6-MeO-THH • 5-MeO-TMT • 5-MeS-DMT • MiPT • α-MT • NET • NMT • PRO-LAD • pyr-T • Tryptamine • Tetrahydroharmine • α,N,O-TMS

v • d • e
Tryptamines

4-Acetoxy-DET • 4-Acetoxy-DIPT • 4-Acetoxy-DMT • 4-HO-DIPT • 5-Bromo-DMT • 5-Fluoro-α-MT • 5-MeO-α-ET  • 5-MeO-α-MT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DIPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MIPT • α-ET • α-MT • Baeocystin • Bufotenin • DET • DiPT • DMT • DPT • Ethocybin • EiPT • Ethocin • Ibogaine • Iprocin • MET • MiPT • Miprocin • Melatonin • NMT • Norbaeocystin • Normelatonin • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Psilocin". A list of authors is available in Wikipedia.
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