Norbaeocystin

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

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

Norbaeocystin is thought to be a prodrug of 4-HT, analogously to how psilocybin is a prodrug of psilocin and baeocystin is thought to be a prodrug of norpsilocin.<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" />

See also

• Aeruginascin
• Baeocystin
• Norpsilocin
• Psilocybin

References

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