Psilocybin
Psilocybin (4-phosphoryloxy-N,N-dimethyltryptamine): Also known as: C12H17N2O4P, 4-PO-DMT, psilocybine, (3-[2-(dimethylamino)-ethyl]-1H-indol-4-ol dihydrogen phosphate)
Psilocybin is a naturally occurring tryptamine alkaloid and psychedelic secondary metabolite that is a prodrug compound produced by more than 200 species of fungi. As a prodrug, psilocybin itself is biologically inactive. It is quickly converted by the body to psilocin by a dephosphorylation reaction mediated by alkaline phosphatase enzymes. Psilocybin is a member of the general class of tryptophan-based compounds that originally functioned as antioxidants in earlier life forms before assuming more complex functions in multicellular organisms, including humans.
It is a substituted tryptamine that features an indole ring linked to an aminoethyl substituent. It was first isolated from fruiting bodies of Psilocybe mexicana cultivated by Albert Hofmann in 1957.
Molecular weight: 248.248 gᐧmol-1
Melting point 224 °C (220-228 oC)[6]
Ammonia-like taste[6]
Relatively stable, white crystalline powder (in pure form)[3]
Can be recrystallized from boiling water
Unstable in light (particularly while in solution)[3][6] + sensitive to temperature[59]
pKa values:
- 1.3 and 6.5 for two consecutive phosphate hydroxyl groups
- 10.4 for the dimethylamine nitrogen
Typically exists as a zwitterionic structure
Soluble in water, methanol and ethanol
Insoluble in organic solvents