Baeocystin is a zwitterionic

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of simila ...

and

analog Analog or analogue may refer to: Computing and electronics * Analog signal, in which information is encoded in a continuous variable ** Analog device, an apparatus that operates on analog signals *** Analog electronics, circuits which use analog ...

psilocybin Psilocybin ( , ) is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. The most potent are members of the genus ''Psilocybe'', such as '' P. azurescens'', '' P. semilanceata'', and '' P.&nbs ...

. It is found as a minor compound in most psilocybin mushrooms together with

norbaeocystin Norbaeocystin 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. Norbaeocysti ...

aeruginascin Aeruginascin or ''N,N,N''-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushroom '' Inocybe aeruginascens'' and '' Pholiotina cyanopus''. Aeruginascin is the ''N''-trimethyl analogue of psiloc ...

, and

psilocin Psilocin (also known as 4-HO-DMT, 4-hydroxy DMT, psilocine, psilocyn, or psilotsin) is a substituted tryptamine alkaloid and a serotonergic psychedelic substance. It is present in most psychedelic mushrooms together with its phosphorylated cou ...

. Baeocystin is an ''N''-demethylated derivative of psilocybin, and a phosphorylated derivative of 4-HO-NMT (4-hydroxy- ''N''-methyltryptamine). The structures at right illustrate baeocystin in its

zwitterion In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium wil ...

ic form. Baeocystin was first isolated from the mushroom '' Psilocybe baeocystis'', and later from '' P. semilanceata'', '' Panaeolus renenosus'', '' Panaeolus subbalteatus'', and '' Copelandia chlorocystis''. It was first synthesized by Troxler ''et al''. in 1959. Little information exists with regard to human

pharmacology Pharmacology is a branch of medicine, biology and pharmaceutical sciences concerned with drug or medication action, where a drug may be defined as any artificial, natural, or endogenous (from within the body) molecule which exerts a biochemica ...

, but in the book ''Magic Mushrooms Around the World'', author Jochen Gartz reports being aware of a study in which "10 mg of baeocystin were found to be about as psychoactive as a similar amount of psilocybin." Gartz also reported in a research paper that a self-administered assay of 4 mg of baeocystin caused "a gentle hallucinogenic experience". While Gartz describes experiencing a "gentle hallucinogenic experience" from baeocystin, this could not be replicated in a mouse model in a 2019 study which found no evidence that baeocystin produces any hallucinogenic effects. Researchers compared psilocybin which is a known hallucinogen to baeocystin by using the mouse head-twitch response. Upon comparison, baeocystin was indistinguishable from saline solution, indicating "...baeocystin alone would likely not induce hallucinogenic effects ''in vivo''". This does contrast however with the human experiences mentioned above, although high quality data is scarce.

References

{{Tryptamines Tryptamine alkaloids Organophosphates Psychedelic tryptamines

See also

References