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