Muscazone

Muscazone
Names
IUPAC name
2-Amino-2-(2-oxo-3H-1,3-oxazol-5-yl)acetic acid
Other names
Muscazon; α-Amino-2,3-dihydro-2-oxo-5-oxazoleacetic acid; α-Amino-2-oxo-4-oxazoline-5-acetic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.141 Edit this at Wikidata
EC Number
  • 218-853-4
UNII
  • InChI=1S/C5H6N2O4/c6-3(4(8)9)2-1-7-5(10)11-2/h1,3H,6H2,(H,7,10)(H,8,9)/t3-/m1/s1 checkY
    Key: ASBGWPLVVIASBE-GSVOUGTGSA-N checkY
  • InChI=1/C5H6N2O4/c6-3(4(8)9)2-1-7-5(10)11-2/h1,3H,6H2,(H,7,10)(H,8,9)/t3-/m1/s1
    Key: ASBGWPLVVIASBE-GSVOUGTGBI
  • O=C([O-])[C@H]([NH3+])C\1=C\NC(=O)O/1
Properties
C5H6N2O4
Molar mass 158.113 g·mol−1
Appearance Crystalline solid
Melting point 190 °C (374 °F; 463 K) (decomposes)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Muscazone is an amino acid derivative found in Amanita muscaria (fly agaric) mushrooms. It is a photodegradation product of ibotenic acid. The human psychoactivity of muscazone is unknown, but it is said to have weak activity in neurochemical tests. Muscazone was first described in the scientific literature by 1965. Other notable compounds found in Amanita muscaria include ibotenic acid, muscimol, and muscarine.

Amanita muscaria contains muscazone.

See also

References

  1. 1 2 Merck Index, 12th Edition, 6390
  2. ↑ Ordak, Michal (26 May 2026). "Amanita muscaria in the evolving novel psychoactive substances landscape - toxicological risks and clinical implications: a narrative review". Frontiers in Pharmacology. 17. doi:10.3389/fphar.2026.1838212. ISSN 1663-9812.
  3. 1 2 Ott J (1996). "Ibotenic Acid–Muscimol: The Primordial Pangk and Amrta" (PDF). Pharmacotheon: Entheogenic Drugs, Their Plant Sources and History (2 ed.). Natural Products Company. pp. 323–358, 446. ISBN 978-0-9614234-8-3. 33. MUSCAZONE [...] Pharmacology: human activity unknown but has weak activity in neurochemical tests (Lanthorn, Searle Co., unpublished communication, Oct. 1986).
  4. ↑ Good R, Mueller GF, Eugster CH (June 1965). "Isolierung und Charakterisierung von Prämuscimol und Muscazon aus Amanita muscaria (L. ex FR.) HOOKER" [Isolation and characterization of premuscimol and muscazone from Amanita muscaria (L. ex FR.) HOOKER]. Helv Chim Acta (in German). 48: 927–930. doi:10.1002/hlca.19650480428. PMID 14321964.
  5. ↑ Eugster CH, Müller GF, Good R (June 1965). "Wirkstoffe aus Amanita muscaria: ibotensaeure und muscazon" [The active ingredients from Amanita muscaria: ibotenic acid and muscazone]. Tetrahedron Lett (in German) (23): 1813–1815. doi:10.1016/s0040-4039(00)90133-3. PMID 5891631.
  6. ↑ Fritz, H., Gagneux, A. R., Zbinden, R., Geigy, J. R., Basle, S. A., & Eugster, C. H. (1965). The structure of muscazone. Tetrahedron Letters, 6(25), 2075–2076. https://scholar.google.com/scholar?cluster=5563476291089816824