CAS:50700-49-7|N-Acetyl-4-benzoquinone Imine

Catalogue Number:A170000
Chemical Name:N-Acetyl-4-benzoquinone Imine
Synonyms:4-(Acetylimino)-2,5-cyclohexadien-1-one; Acetimidoquinone; N-Acetyl-p-benzoquinonimine; NAPQI;
CAS Number:50700-49-7
Molecular Formula:C₈H₇NO₂
Appearance:Pale Yellow to Very Dark Orange Solid
Melting Point:>58C (dec.)
Molecular Weight:149.15
Storage:- 86°C
Solubility:Chloroform (Slightly, Sonicated), DMSO (Slightly)
Stability
Air Sensitive, Light Sensitive, Moisture Sensitive, Temperature Sensitive
Category:Standards; Pharmaceutical/API Drug Impurities/Metabolites;
Applications:N-Acetyl-4-benzoquinone Imine (NAPQI) is a toxic metabolite of Acetaminophen (A161220), an analgesic and antipyretic agent used as a pain reliever to treat headache, muscle aches, and arthritis (1,2,3). N-Acetyl-4-benzoquinone Imine can react with cysteine residues of hepatic proteins to yield Acetaminophen-cysteine (A161255) (4).
References:(1) Jaeschke, H., et al.: Toxicol. Sci., 89, 31 (2006)
(2) O’Malley G. F., et al.: J Med Toxicol. 11, 317 (2015)
(3) McGill, M. R. and Jaeschke, H. Pharm Res. 30, 2174 (2013)
(4) Frey, S. M., et al.: J Med Toxicol. 11, 218 (2015)
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