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Psilocin
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| Systematic (IUPAC) name | |
| 4-Hydroxy-N,N-dimethyl-tryptamine | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C12H16N2O |
| Mol. mass | 204.27 g/mol |
| SMILES | & |
| 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 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; FeCl3 / methanol / hydrochloric acid).
Structural analogs
Sulfur analogs are known with a benzothienyl replacement2 as well as 4-SH-DMT3. 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 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, and 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 physiological half-life ranges from 2 to 3 hours.6
- See psilocybin for more details
Behavioral and Non-behavioral Effects
The general characteristics of the hallucinogenic effects induced by psilocin are virtually identical to those induced by mescaline, except the duration of its effect are comparatively shorter, lasting approximately 6-8 hours.5
Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion can include 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 LSD.5
See also
References
- ^ "Green list"
- ^ Chapman (1972) Perkin Trans. 1, 3011
- ^ Hofmann, Swiss 421,960 (1967); CA 68:95680n
- ^ a b Sard (2005): PMID 16061378
- ^ a b c d e f Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
- ^ a b Psilocybin Investigator’s Brochure
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
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Wikipedia content modification information:
- This page was last modified on 26 December 2008, at 10:07.
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