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Skeletal formula of baeocystin as a zwitterion
Space-filling model of the baeocystin molecule as a zwitterion
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Molar mass270.225 g·mol−1
3D model (JSmol)

Baeocystin is a zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, and psilocin. 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 zwitterionic form.

Baeocystin was first isolated from the mushroom Psilocybe baeocystis,[1] and later from P. semilanceata,[2] Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis.[3] It was first synthesized by Troxler et al. in 1959.[4]

Little information exists with regard to human pharmacology, 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."[5] Gartz also reported in a research paper that a self-administered assay of 4 mg of baeocystin caused "a gentle hallucinogenic experience".[6].

Even though Gartz describes a "gentle hallucinogenic experience" from baeocystin, his report conflicts with the data presented by a more recent study released in 2019. The study asserts baeocystin does not produce any hallucinogenic effects.[7] Researchers compared psilocybin, 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".

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  1. ^ Leung AY, Paul AG (1968). "Baeocystin and norbaeocystin: New analogs of psilocybin from Psilocybe baeocystis". Journal of Pharmaceutical Sciences. 57 (10): 1667–71. doi:10.1002/jps.2600571007. PMID 5684732.
  2. ^ Repke DB, Leslie DT, Guzman G (1977). "Baeocystin in Psilocybe, Conocybe and Panaeolus". Lloydia. 40 (6): 566–78. PMID 600026.
  3. ^ Brossi A. (1988). The Alkaloids: Chemistry and Pharmacology V32: Chemistry and Pharmacology. Academic Press. p. 46. ISBN 978-0-08-086556-0.
  4. ^ Troxler, F.; Seeman, F.; Hofmann, A. (1959). "Abwandlungsprodukte von Psilocybin und Psilocin. 2. Mitteilung über synthetische Indolverbindungen". Helvetica Chimica Acta (in German). 42 (6): 2073–2103. doi:10.1002/hlca.19590420638.
  5. ^ Gartz J. (1997). Magic Mushrooms Around the World. Los Angeles, California: LIS Publications. p. 27. ISBN 978-0-9653399-0-2.
  6. ^ Gartz J. (1991). "Further Investigations on Psychoactive Mushrooms of the Genera Psylocibe, Gymnopilus and Conocybe" (PDF). Ann. Mus. Civ. Rovereto. 7: 265–74.
  7. ^ Sherwood, Alexander. "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin,and Aeruginascin". Journal of Natural Products. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061.