Baeocystin

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).<ref>Template:Cite journal</ref> 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.<ref name="GartzAppeliusTaake1996">Template:Cite book</ref><ref name="Gartz1999">Template:Cite book</ref><ref name="Gartz1992">Template:Cite journal</ref><ref name="Ott1996">Template:Cite book</ref><ref name="Trout2007">Template:Cite book</ref><ref name="MorrisOtt2023">Template:Cite podcast</ref> He has stated that 4Template:Nbspmg produced a "threshold" or "gentle hallucinogenic experience" with "mild hallucinations for three hours" and that "10Template:Nbspmg of baeocystin [was] found to be about as psychoactive as a similar amount of psilocybin".<ref name="GartzAppeliusTaake1996" /><ref name="Gartz1999" /><ref name="Gartz1992" /><ref name="Ott1996" /><ref name="Trout2007" /> Gartz also personally communicated these findings to Jonathan Ott, who has reproduced the claims.<ref name="Ott1996" /><ref name="Trout2007" /><ref name="MorrisOtt2023" /> Hamilton Morris has expressed surprise and skepticism about the reported psychoactivity of baeocystin however.<ref name="MorrisOtt2023" />

Gartz has also claimed that mushrooms with high baeocystin content, such as Psilocybe semilanceata, are more frequently associated with dysphoric experiences.<ref name="PepeHesamidelaCerda2023">Template:Cite journal</ref><ref name="Gartz1989">Template:Cite journal</ref> 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.<ref name="PepeHesamidelaCerda2023" /><ref name="Gartz1989" /> However, more research is needed on the effects of baeocystin and aeruginascin in humans.<ref name="PepeHesamidelaCerda2023" /><ref name="Gartz1989" />

In contrast to Gartz, mycologist Paul Stamets has reported that he tried 10Template:Nbspmg pure baeocystin and that it didn't produce hallucinogenic effects, but did produce pupil dilation and apparent anxiolysis.<ref name="Mandrake2021">Template:Cite web</ref><ref name="Rogan2019">Template:Cite podcast</ref><ref name="Bauer2020">Template:Cite web</ref>

Pharmacology

Baeocystin is thought to be a prodrug of norpsilocin, analogously to how psilocybin is a prodrug of psilocin.<ref name="RakoczyRungeSen2024">Template:Cite journal</ref> Norpsilocin is a potent and centrally penetrant agonist of the serotonin 5-HT_2A receptor and also interacts with other serotonin receptors.<ref name="RakoczyRungeSen2024" />

Baeocystin and norpsilocin have been found to be inactive in terms of hallucinogen-like effects in rodents in multiple studies published in the 2020s.<ref name="SherwoodHalberstadtKlein2020">Template:Cite journal</ref><ref name="GlatfelterPottiePartilla2022">Template:Cite journal</ref><ref name="RakoczyRungeSen2024" /> 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.<ref name="SherwoodHalberstadtKlein2020" /><ref name="GlatfelterPottiePartilla2022" /><ref name="RakoczyRungeSen2024" /> In one of the papers, the researchers concluded that "...baeocystin alone would likely not induce hallucinogenic effects in vivo".<ref name="SherwoodHalberstadtKlein2020" /> As with baeocystin and norpsilocin, norbaeocystin, aeruginascin, 4-hydroxytryptamine (4-HT), and 4-HO-TMT also all failed to induce the HTR in rodents.<ref name="SherwoodHalberstadtKlein2020" /><ref name="GlatfelterPottiePartilla2022" /><ref name="RakoczyRungeSen2024" /> However, these compounds have not necessarily been inactive in terms of behavioral effects in general.<ref name="GlatfelterPottiePartilla2022" /><ref name="RakoczyRungeSen2024" />

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-HT_2A receptor agonists and producing other centrally mediated behavioral effects in animals, remain unknown.<ref name="RakoczyRungeSen2024" /><ref name="GlatfelterPottiePartilla2022" /> One possibility however is that these compounds may be biased agonists of the serotonin 5-HT_2A receptor and may not sufficiently activate the intracellular signaling cascades responsible for psychedelic effects.<ref name="RakoczyRungeSen2024" /><ref name="GlatfelterPottiePartilla2022" /> 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.<ref name="DandaMazochováŠíchová2025">Template:Cite journal</ref>

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,<ref name="Leung 1968"/> and later from P. semilanceata,<ref name="Repke 1977"/> Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis.<ref name="Brossi 1988"/>

History

Baeocystin was first synthesized by Troxler and colleagues in 1959.<ref name="Troxer 1959"/>

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.<ref name="AdisInsight">Template:Cite web</ref>

See also

• Substituted tryptamine

References

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