Baeocystin

Baeocystin
Skeletal formula of baeocystin as a zwitterion
Space-filling model of the baeocystin molecule as a zwitterion
Clinical data
Other namesNorpsilocybin; N-Desmethylpsilocybin; 4-Phosphoryloxy-N-methyltryptamine; 4-PO-NMT; 4-Hydroxy-N-methyltryptamine 4-phosphate; PLZ-1019
Routes of
administration		Oral
ATC code
  • None
Legal status
Legal status
Identifiers
  • 3-[2-(Methylammonio)ethyl]-1H-indol-4-yl hydrogenphosphate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC11H15N2O4P
Molar mass270.225 g·mol−1
3D model (JSmol)
  • CNCCc1c[nH]c2cccc(OP(=O)(O)O)c12
  • 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) checkY
  • Key:WTPBXXCVZZZXKR-UHFFFAOYSA-N checkY
  (verify)

Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is a zwitterionic alkaloid and analog of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin.[1] 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,[2] and later from P. semilanceata,[3] Panaeolus renenosus, Panaeolus subbalteatus, and Copelandia chlorocystis.[4] It was first synthesized by Troxler et al. in 1959.[5]

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."[6] Gartz also reported in a research paper that a self-administered assay of 4 mg of baeocystin caused "a gentle hallucinogenic experience".[7]

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.[8] 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.

Baeocystin is thought to be a prodrug of norpsilocin, analogously to how psilocybin is a prodrug of psilocin.[9] Norpsilocin is a potent and centrally penetrant agonist of the serotonin 5-HT2A receptor and also interacts with other serotonin receptors.[9] The reasons for the non-hallucinogenic nature of norpsilocin and baecystin remain unknown.[9]

It is being evaluated under the developmental code name PLZ-1019 for the possible treatment of pervasive developmental disorders in children.[10]

See also

References

  1. ^ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022). "Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids". International Journal of Molecular Sciences. 23 (22): 14068. doi:10.3390/ijms232214068. PMC 9693126. PMID 36430546.
  2. ^ Leung AY, Paul AG (October 1968). "Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis". Journal of Pharmaceutical Sciences. 57 (10): 1667–1671. doi:10.1002/jps.2600571007. PMID 5684732.
  3. ^ Repke DB, Leslie DT, Guzmán G (1977). "Baeocystin in psilocybe, conocybe and panaeolus". Lloydia. 40 (6): 566–578. PMID 600026.
  4. ^ Brossi A (1988). The Alkaloids: Chemistry and Pharmacology V32: Chemistry and Pharmacology. Academic Press. p. 46. ISBN 978-0-08-086556-0.
  5. ^ 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.
  6. ^ Gartz J (1997). Magic Mushrooms Around the World. Los Angeles, California: LIS Publications. p. 27. ISBN 978-0-9653399-0-2.
  7. ^ Gartz J (1991). "Further Investigations on Psychoactive Mushrooms of the Genera Psylocibe, Gymnopilus and Conocybe" (PDF). Ann. Mus. Civ. Rovereto. 7: 265–74.
  8. ^ Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P (February 2020). "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. PMID 32077284.
  9. ^ a b c Rakoczy RJ, Runge GN, Sen AK, Sandoval O, Wells HG, Nguyen Q, Roberts BR, Sciortino JH, Gibbons WJ, Friedberg LM, Jones JA, McMurray MS (October 2024). "Pharmacological and behavioural effects of tryptamines present in psilocybin-containing mushrooms". Br J Pharmacol. 181 (19): 3627–3641. doi:10.1111/bph.16466. PMID 38825326.
  10. ^ "Baeocystin - Pilz Bioscience". AdisInsight. 19 January 2021. Retrieved 27 October 2024.