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'''Norbaeocystin''' is a [[psilocybin mushroom]] [[alkaloid]] and [[analog (chemistry)|analog]] of [[psilocybin]]. It is found as a minor compound in most [[psilocybin mushroom]]s together with [[psilocin]], [[psilocybin]], [[aeruginascin]], and [[baeocystin]], from which it is a derivative.<ref name="Leung_1968">{{cite journal | vauthors = Leung AY, Paul AG | title = Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis | journal = Journal of Pharmaceutical Sciences | volume = 57 | issue = 10 | pages = 1667–71 | date = October 1968 | pmid = 5684732 | doi = 10.1002/jps.2600571007 }}</ref><ref>{{Cite journal |last1=Gotvaldova |first1=Klara |last2=Borovicka |first2=Jan |last3=Hajkova |first3=Katerina |last4=Cihlarova |first4=Petra |last5=Rockefeller |first5=Alan |last6=Kuchar |first6=Martin |year=2022 |title=Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids |journal=International Journal of Molecular Sciences |volume=23 |issue=22 |language=en |pages=14068 |doi=10.3390/ijms232214068 |issn=1422-0067|doi-access=free }}</ref>
'''Norbaeocystin''' is a [[psilocybin mushroom]] [[alkaloid]] and [[analog (chemistry)|analog]] of [[psilocybin]]. It is found as a minor compound in most [[psilocybin mushroom]]s together with [[psilocin]], [[psilocybin]], [[aeruginascin]], and [[baeocystin]], from which it is a derivative.<ref name="Leung_1968">{{cite journal | vauthors = Leung AY, Paul AG | title = Baeocystin and norbaeocystin: new analogs of psilocybin from Psilocybe baeocystis | journal = Journal of Pharmaceutical Sciences | volume = 57 | issue = 10 | pages = 1667–1671 | date = October 1968 | pmid = 5684732 | doi = 10.1002/jps.2600571007 }}</ref><ref>{{cite journal | vauthors = Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M | title = Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids | journal = International Journal of Molecular Sciences | volume = 23 | issue = 22 | pages = 14068 | date = November 2022 | pmid = 36430546 | doi = 10.3390/ijms232214068 | pmc = 9693126 | doi-access = free }}</ref>


Norbaeocystin is a N-demethylated derivative of baeocystin (itself a N-demethylated derivative of psilocybin), and a phosphorylated derivative of [[4-hydroxytryptamine]]. The latter is notable as a positional isomer of [[serotonin]], which is 5-hydroxytryptamine.
Norbaeocystin is a N-demethylated derivative of baeocystin (itself a N-demethylated derivative of psilocybin), and a phosphorylated derivative of [[4-hydroxytryptamine]]. The latter is notable as a positional isomer of [[serotonin]], which is 5-hydroxytryptamine.

Revision as of 20:26, 20 June 2023

Norbaeocystin
Skeletal formula of norbaeocystin
Space-filling model of the norbaeocystin molecule as a zwitterion
Clinical data
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-(2-ammonioethyl)-1H-indol-4-yl hydrogen phosphate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC10H13N2O4P
Molar mass256.198 g·mol−1
3D model (JSmol)
  • NCCc1c[nH]c2cccc(OP(=O)(O)O)c12
  • InChI=1S/C10H13N2O4P/c11-5-4-7-6-12-8-2-1-3-9(10(7)8)16-17(13,14)15/h1-3,6,12H,4-5,11H2,(H2,13,14,15)
  • Key:IKQGYCWFBVEAKF-UHFFFAOYSA-N
  (verify)

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.[1][2]

Norbaeocystin is a N-demethylated derivative of baeocystin (itself a N-demethylated derivative of psilocybin), and a phosphorylated derivative of 4-hydroxytryptamine. The latter is notable as a positional isomer of serotonin, which is 5-hydroxytryptamine.

See also

References

  1. ^ 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.
  2. ^ 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.