Psilocin



Psilocin
Systematic (IUPAC) name
4-Hydroxy-N,N-dimethyl-tryptamine
Identifiers
CAS number 520-53-6
ATC code  ?
PubChem 4980
Chemical data
O 
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 (Convention on Psychotropic Substances.[1]

History

The Swiss chemist Psilocybe mushrooms in 1959 guided by self-administration.

Chemistry

Psilocin can be obtained by synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole.

Psilocin is relatively unstable in solution due to its 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.