baeocystin

Baeocystin is a naturally occurring psychoactive compound in the tryptamine family. It is a phosphorylated analog of tryptamine and is closely related to psilocybin and psilocin. Baeocystin is 4-phosphoryloxy-N-methyltryptamine, making it the N-methyl analogue of the non-phosphorylated compound and a lower-mos potency member of the psilocybin family.

Occurrence and biosynthesis: Baeocystin is found in a range of psilocybin-containing mushrooms, often alongside psilocybin and psilocin but in smaller amounts. In the mushroom, it is produced through the same general biosynthetic pathway that yields psilocybin, involving tryptophan decarboxylation, N-methylation, and phosphorylation steps. Specific enzymes in Psilocybe species contribute to the formation of baeocystin, psilocybin, and related compounds, with baeocystin sometimes considered a byproduct or intermediate in these pathways.

Pharmacology and effects: Baeocystin is thought to be a prodrug that can be dephosphorylated to 4-hydroxy-N-methyltryptamine, a compound with its own activity distinct from psilocin. The precise potency and contribution of baeocystin to the psychedelic effects of psilocybin-containing mushrooms are not well established, and pharmacological data remain limited compared with psilocybin and psilocin.

Legal and research context: As part of the psilocybin-producing system in certain mushrooms, baeocystin is included in discussions of natural products with psychedelic activity. Research on its pharmacokinetics, metabolism, and subjective effects continues to be limited, and regulatory treatment generally follows that of psilocybin-containing materials.