psilocybin

Chemistry

Psilocybin (O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine) is a prodrug that is converted into the pharmacologically active compound psilocin in the body by a dephosphorylation reaction.[20] This chemical reaction takes place under strongly acidic conditions, or under physiological conditions in the body, through the action of enzymes called phosphatases. Psilocybin is a tryptamine compound having a chemical structure derived from tryptophan and containing a ring configuration called an indole linked to an ethylamine substituent. It bears a close structural resemblance to the neurotransmitter serotonin (5-hydroxytryptamine). Psilocybin is a zwitterionic alkaloid that is soluble in water, moderately soluble in methanol and ethanol, and insoluble in most organic solvents. Exposure to light is detrimental to the stability of aqueous solutions of psilocybin, and will cause it to rapidly oxidize—an important consideration when using it as an analytical standard.[21] A method for the large-scale synthesis of psilocybin was reported by a Japanese group in 2003.[22]