Psilocin

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Psilocin
Legal status
Legal status
Identifiers
CAS Number
E number{{#property:P628}}
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Chemical and physical data
FormulaC12H16N2O
Molar mass204.27 g/mol
3D model (JSmol)
Melting point173 to 176 °C (Expression error: Unrecognized word "to". °F)

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Overview

Psilocin,(4-HO-DMT) sometimes called psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its close congener psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.[1]

Psilocin is almost identical to the chemical structure of the chemical of another known hallucinogen, bufotenin. The only difference is the position of the hydroxyl (OH-) group on the benzene ring — in psilocin, the hydroxyl group is at the 4-position, while in bufotenin it is at the 5-position.

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). One synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

Psilocin is relatively unstable in solution due to its phenolic OH group. Under alkaline conditions in the presence of oxygen it immediately 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). Psilocin is an amine and forms salts with acids [citation needed] that are usually more stable upon storage. Psilocin base can be evaporated by heating.

Pharmacology

Psilocybin is rapidly dephosphorylated in the body to psilocin 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). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.

See also

References

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

Cost Effectiveness of Psilocin

| group5 = Clinical Trials Involving Psilocin | list5 = Ongoing Trials on Psilocin at Clinical Trials.govTrial results on PsilocinClinical Trials on Psilocin at Google


| group6 = Guidelines / Policies / Government Resources (FDA/CDC) Regarding Psilocin | list6 = US National Guidelines Clearinghouse on PsilocinNICE Guidance on PsilocinNHS PRODIGY GuidanceFDA on PsilocinCDC on Psilocin


| group7 = Textbook Information on Psilocin | list7 = Books and Textbook Information on Psilocin


| group8 = Pharmacology Resources on Psilocin | list8 = AND (Dose)}} Dosing of PsilocinAND (drug interactions)}} Drug interactions with PsilocinAND (side effects)}} Side effects of PsilocinAND (Allergy)}} Allergic reactions to PsilocinAND (overdose)}} Overdose information on PsilocinAND (carcinogenicity)}} Carcinogenicity information on PsilocinAND (pregnancy)}} Psilocin in pregnancyAND (pharmacokinetics)}} Pharmacokinetics of Psilocin


| group9 = Genetics, Pharmacogenomics, and Proteinomics of Psilocin | list9 = AND (pharmacogenomics)}} Genetics of PsilocinAND (pharmacogenomics)}} Pharmacogenomics of PsilocinAND (proteomics)}} Proteomics of Psilocin


| group10 = Newstories on Psilocin | list10 = Psilocin in the newsBe alerted to news on PsilocinNews trends on Psilocin


| group11 = Commentary on Psilocin | list11 = Blogs on Psilocin

| group12 = Patient Resources on Psilocin | list12 = Patient resources on PsilocinDiscussion groups on PsilocinPatient Handouts on PsilocinDirections to Hospitals Treating PsilocinRisk calculators and risk factors for Psilocin


| group13 = Healthcare Provider Resources on Psilocin | list13 = Symptoms of PsilocinCauses & Risk Factors for PsilocinDiagnostic studies for PsilocinTreatment of Psilocin

| group14 = Continuing Medical Education (CME) Programs on Psilocin | list14 = CME Programs on Psilocin

| group15 = International Resources on Psilocin | list15 = Psilocin en EspanolPsilocin en Francais

| group16 = Business Resources on Psilocin | list16 = Psilocin in the MarketplacePatents on Psilocin

| group17 = Informatics Resources on Psilocin | list17 = List of terms related to Psilocin


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