Norbaeocystin

Norbaeocystin, also known as 4-phosphoryloxytryptamine (4-PO-T), is a psilocybin mushroom alkaloid of the tryptamine family and an analogue of psilocybin (4-PO-DMT). It is found as a minor compound in most psilocybin mushrooms, together with psilocybin, psilocin (4-HO-DMT), aeruginascin (4-PO-TMT), and baeocystin (4-PO-NMT), from which it is a derivative.<ref name="Leung_1968">Template:Cite journal</ref><ref>Template:Cite journal</ref>

Pharmacology

Norbaeocystin (4-PO-T) is thought to be a prodrug of 4-hydroxytryptamine (4-HT), analogously to how psilocybin (4-PO-DMT) is a prodrug of psilocin (4-HO-DMT) and baeocystin (4-PO-NMT) is thought to be a prodrug of norpsilocin (4-HO-NMT).<ref name="RakoczyRungeSen2024">Template:Cite journal</ref><ref name="SherwoodHalberstadtKlein2020">Template:Cite journal</ref> 4-HT is a potent and centrally penetrant serotonin 5-HT_2A receptor agonist and also interacts with other serotonin receptors.<ref name="RakoczyRungeSen2024" /> In spite of this however, 4-HT and norbaeocystin do not produce the head-twitch response, a behavioral proxy of psychedelic effects, in animals, and hence are putatively non-hallucinogenic.<ref name="RakoczyRungeSen2024" /><ref name="SherwoodHalberstadtKlein2020" /> The reasons for this are unknown, but may be due to β-arrestin2-preferring biased agonism of the serotonin 5-HT_2A receptor.<ref name="RakoczyRungeSen2024" />

Norbaeocystin is an N-demethylated derivative of baeocystin (itself an N-demethylated derivative of psilocybin), and a phosphorylated derivative of 4-hydroxytryptamine (4-HT).Template:Citation needed The latter is notable as a positional isomer of serotonin, which is 5-hydroxytryptamine (5-HT).Template:Citation needed

Derivatives of norbaeocystin (4-PO-T), also known as substituted 4-phosphoryloxytryptamines, include baeocystin (4-PO-NMT), psilocybin (4-PO-DMT), ethocybin (4-PO-DET), 4-PO-DiPT, 4-PO-MET, and aeruginascin (4-PO-TMT), among others.