Psilocin

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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	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 1 History 2 Chemistry 2.1 Structural analogs 3 Pharmacology 4 Behavioral and Non-behavioral Effects 5 See also 6 References 7 External links

[edit] 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.

[edit] 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).

[edit] Structural analogs

Sulfur analogs are known with a benzothienyl replacement^[2] as well as 4-SH-DMT^[3]. N¹-methylpsilocin is a functionally 5-HT_2C receptor prefering agonists.^[4] 4-fluoro-N,N-dimethyltryptamine is known.^[5]

[edit] 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 5HT_2A, 5HT_2C and 5HT_1A agonist. Psilocin is structurally similar to serotonin (5-HT)^[6], and its effects are thought to come from its ability to mimic serotonin and thereby activate serotonin receptors in the brain.^{[citation needed]}

Psilocin has no significant effect on dopamine receptors (unlike LSD) and only affects the noradrenergic system at very high dosages.^[7]

Psilocin physiological half-life ranges from 2 to 3 hours.^[8]

See psilocybin for more details

[edit] 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.^[6]

Its physiological effects are similar to a sympathetic arousal state. Specific effects observed after ingestion can include increased heart rate, dilated pupils, restlessness or arousal, euphoria, open and closed eye visuals (common at medium to high doses), synthesesia (eg. hearing colours and seeing sounds), increased body temperature, headache, sweating and chills, and nausea.^[6]

There is virtually no direct lethality associated with psilocin.^[6] There is virtually no withdrawal syndrome when chronic use of this drug is ceased.^[6] There is cross tolerance among psilocin, mescaline, and LSD.^[6]

[edit] See also

• Psychedelic mushrooms
• Psilocybin
• Tryptamine
• Indole
• Psychedelic drug
• Psychoactive drug

[edit] References

1. ^ "Green list"
2. ^ Chapman (1972) Perkin Trans. 1, 3011
3. ^ Hofmann, Swiss 421,960 (1967); CA 68:95680n
4. ^ Sard (2005): PMID 16061378
5. ^ Cite error: Invalid <ref> tag; no text was provided for refs named Sard
6. ^ ^{a b c d e f} Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
7. ^ Psilocybin Investigator’s Brochure
8. ^ Psilocybin Investigator’s Brochure

[edit] 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

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 • Aeruginascin • 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