Norbaeocystin
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| Other names | 4-Phosphoryloxytryptamine; 4-PO-T; 4-Hydroxytryptamine 4-phosphate; 4-Hydroxytryptamine phosphate |
| Routes of administration | Oral |
| Drug class | Serotonin receptor agonist; Non-hallucinogenic serotonin 5-HT2A receptor agonist |
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| Formula | C10H13N2O4P |
| Molar mass | 256.198 g·mol−1 |
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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.
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. 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.