Baeocystin

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Baeocystin
Skeletal formula of baeocystin as a zwitterion
Space-filling model of the baeocystin molecule as a zwitterion
Systematic (IUPAC) name
3-[2-(Methylammonio)ethyl]-1H-indol-4-yl hydrogenphosphate
Clinical data
Legal status
Routes of
administration
Oral
Identifiers
CAS Number 21420-58-6 YesY
ATC code none
PubChem CID: 161359
ChemSpider 141741 YesY
Chemical data
Formula C11H15N2O4P
Molecular mass 270.222 g/mol
  • O=P(O)(O)Oc1cccc2c1c(cn2)CCNC
  • InChI=1S/C11H15N2O4P/c1-12-6-5-8-7-13-9-3-2-4-10(11(8)9)17-18(14,15)16/h2-4,7,12-13H,5-6H2,1H3,(H2,14,15,16) YesY
  • Key:WTPBXXCVZZZXKR-UHFFFAOYSA-N YesY
  (verify)

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

References

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