Norbaeocystin Explained

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.^{[1] [2]}

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.^{[3] [4]} 4-HT is a potent and centrally penetrant serotonin 5-HT_2A 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-HT_2A receptor.

See also

• Aeruginascin
• Baeocystin
• Norpsilocin
• Psilocybin

Notes and References

1. Leung AY, Paul AG . Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis . Journal of Pharmaceutical Sciences . 57 . 10 . 1667–1671 . October 1968 . 5684732 . 10.1002/jps.2600571007 .
2. Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M . Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids . International Journal of Molecular Sciences . 23 . 22 . 14068 . November 2022 . 36430546 . 10.3390/ijms232214068 . 9693126 . free .
3. Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS . Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms . Br J Pharmacol . 181 . 19 . 3627–3641 . October 2024 . 38825326 . 10.1111/bph.16466 . free .
4. Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P . Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin . J Nat Prod . 83 . 2 . 461–467 . February 2020 . 32077284 . 10.1021/acs.jnatprod.9b01061 .