Norbaeocystin
Norbaeocystin, also known as 4-phosphoryloxytryptamine, is a psilocybin mushroom alkaloid of the tryptamine family and an analogue of psilocybin. It is found as a minor compound in most psilocybin mushrooms, together with psilocybin, psilocin, aeruginascin, and baeocystin, from which it is a derivative.
Norbaeocystin is generally thought to be non-psychoactive, although this has not been confirmed.
Pharmacology
Norbaeocystin is thought to be a prodrug of 4-hydroxytryptamine, analogously to how psilocybin is a prodrug of psilocin and baeocystin is thought to be a prodrug of norpsilocin. 4-HT is a potent and centrally penetrant serotonin 5-HT2A receptor agonist and also interacts with other serotonin receptors. 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. The reasons for this are unknown, but may be due to β-arrestin2-preferring biased agonism of the serotonin 5-HT2A receptor.
Chemistry
Norbaeocystin is an N-demethylated derivative of baeocystin, and a phosphorylated derivative of 4-hydroxytryptamine. The latter is notable as a positional isomer of serotonin, which is 5-hydroxytryptamine.
Derivatives
Derivatives of norbaeocystin, also known as substituted 4-phosphoryloxytryptamines, include baeocystin, psilocybin, ethocybin, 4-PO-DiPT, 4-PO-MET, and aeruginascin, among others.
History
Norbaeocystin was found to be sold as an analytical standard in 2023.