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
CAS Number	2255-39-2 ;
3D model (JSmol)	Interactive image;
ChemSpider	16735919 ;
ECHA InfoCard	100.017.141
EC Number	218-853-4;
PubChem CID	92925;
UNII	K97K88B7WE ;
CompTox Dashboard (EPA)	DTXSID80893775 ;
	InChI 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 Key: ASBGWPLVVIASBE-GSVOUGTGSA-N ; 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;
	SMILES O=C([O-])[C@H]([NH3+])C\1=C\NC(=O)O/1;
Properties
Chemical formula	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). verify (what is ?) Infobox references

Muscazone is an amino acid derivative found in Amanita muscaria (fly agaric) mushrooms.^[1] It is a photodegradation product of ibotenic acid.^[2] The human psychoactivity of muscazone is unknown, but it is said to have weak activity in neurochemical tests.^[3] Muscazone was first described in the scientific literature by 1965.^[4]^[5]^[6] Other notable compounds found in Amanita muscaria include ibotenic acid, muscimol, and muscarine.^[3]

References

1 2 Merck Index, 12th Edition, 6390
↑ 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.
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 Pharmacology: human activity unknown but has weak activity in neurochemical tests (Lanthorn, Searle Co., unpublished communication, Oct. 1986).
↑ 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.
↑ 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.
↑ 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

External links

Muscazone - Isomer Design

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[Merck-1] 1 2 Merck Index, 12th Edition, 6390

[Ordak2026-2] 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.

[Ott1996-3] 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).

[GoodMuellerEugster1965-4] 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.

[EugsterMüller1965-5] 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.

[FritzGagneuxZbinden1965-6] 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

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Muscazone

See also

References

External links