Baeocystin
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Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is a zwitterionic 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), norbaeocystin (4-PO-T), and aeruginascin (4-PO-TMT).[1] The compound is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of norpsilocin (4-HO-NMT).
Use and effects
Chemist and mycologist Jochen Gartz reported in the 1990s that baeocystin is active as a psychedelic in humans.[2][3][4][5][6][7] He has stated that 4Script error: No such module "String".mg produced a "threshold" or "gentle hallucinogenic experience" with "mild hallucinations for three hours" and that "10Script error: No such module "String".mg of baeocystin [was] found to be about as psychoactive as a similar amount of psilocybin".[2][3][4][5][6] Gartz also personally communicated these findings to Jonathan Ott, who has reproduced the claims.[5][6][7] Hamilton Morris has expressed surprise and skepticism about the reported psychoactivity of baeocystin however.[7]
Gartz has also claimed that mushrooms with high baeocystin content, such as Psilocybe semilanceata, are more frequently associated with dysphoric experiences.[8][9] Conversely, he has claimed that accidental ingestion of Inocybe aeruginascens, which contains high levels of both aeruginascin (4-PO-TMT) and baeocystin, is usually associated with euphoric experiences, in contrast to the dysphoric experiences that can occur with mushrooms containing only high levels of psilocybin.[8][9] However, more research is needed on the effects of baeocystin and aeruginascin in humans.[8][9]
In contrast to Gartz, mycologist Paul Stamets has reported that he tried 10Script error: No such module "String".mg pure baeocystin and that it didn't produce hallucinogenic effects, but did produce pupil dilation and apparent anxiolysis.[10][11][12]
Interactions
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Pharmacology
Baeocystin is thought to be a prodrug of norpsilocin, analogously to how psilocybin is a prodrug of psilocin.[13] Norpsilocin is a potent and centrally penetrant agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors.[13]
Baeocystin and norpsilocin have been found to be inactive in terms of hallucinogen-like effects in rodents in multiple studies published in the 2020s.[14][15][13] More specifically, they were unable to produce the head-twitch response (HTR), a well-established behavioral proxy of psychedelic effects, and this was in contrast to psilocybin.[14][15][13] In one of the papers, the researchers concluded that "...baeocystin alone would likely not induce hallucinogenic effects in vivo".[14] As with baeocystin and norpsilocin, norbaeocystin, aeruginascin, 4-hydroxytryptamine (4-HT), and 4-HO-TMT also all failed to induce the HTR in rodents.[14][15][13] However, these compounds have not necessarily been inactive in terms of behavioral effects in general.[15][13]
The reasons for the apparently non-hallucinogenic nature of norpsilocin, baeocystin, and related compounds in animals (and possibly in humans), in spite of norpsilocin and others being potent serotonin 5-HT2A receptor agonists and producing other centrally mediated behavioral effects in animals, remain unknown.[13][15] One possibility however is that these compounds may be biased agonists of the serotonin 5-HT2A receptor and may not sufficiently activate the intracellular signaling cascades responsible for psychedelic effects.[13][15] On the other hand, a 2025 animal study found that both baeocystin and norpsilocin are peripherally selective with very limited ability to cross the blood–brain barrier.[16]
Chemistry
Analogues
Analogues of baeocystin include 4-HO-NMT, norbaeocystin (4-PO-T), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), ethocybin (4-PO-DET), and aeruginascin (4-PO-TMT), among others.
Natural occurrence
Baeocystin was first isolated from the mushroom Psilocybe baeocystis,[17] and later from P. semilanceata,[18] Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis.[19]
History
Baeocystin was first synthesized by Troxler and colleagues in 1959.[20]
Research
Baeocystin is being evaluated by Pilz Bioscience ("pilz" being German for "mushroom") under the developmental code name PLZ-1019 for the possible treatment of pervasive developmental disorders like autism in children.[21]
See also
References
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