A potent hallucinogenic compound, C12H16N2O, related to psilocybin.
[PSILOC(YBIN) + -IN.]
psilocin
Dictionary:
psil·o·cin (sĭl'ə-sĭn, sī'lə-)  |
| 5min Related Video: psilocin |
| Medical Dictionary: psil·o·cin |
| WordNet: psilocin |
Note: click on a word meaning below to see its connections and related words.
The noun has one meaning:
Meaning #1:
a hallucinogenic compound obtained from a mushroom
Synonym: psilocybin
| Wikipedia: Psilocin |
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| 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 | |
| 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-hydroxy-dimethyltryptamine, 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] 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 ability to perceive time.
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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 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
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 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 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
- Psilocin (4-HO-DMT) entry in TiHKAL • info
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 | psilocybin |
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| hallucinogenic drug (drug – in law) |
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 | Dictionary. The American Heritage® Dictionary of the English Language, Fourth Edition Copyright © 2007, 2000 by Houghton Mifflin Company. Updated in 2009. Published by Houghton Mifflin Company. All rights reserved. Read more |
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| Medical Dictionary. The American Heritage® Stedman's Medical Dictionary Copyright © 2002, 2001, 1995 by Houghton Mifflin Company. Read more |
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| WordNet. WordNet 1.7.1 Copyright © 2001 by Princeton University. All rights reserved. Read more |
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