N-Acetyl-4-benzoquinone Imine

CAS: 50700-49-7

Ref. TR-A170000

Product Information

• Name: N-Acetyl-4-benzoquinone Imine
• Synonyms: N-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide, Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)-, Acetimidoquinone, N-(4-Oxo-2,5-cyclohexadien-1-ylidene)acetamide, N-Acetyl-1,4-benzoquinonimine, N-Acetyl-p-benzoquinone imine, N-Acetyl-p-benzoquinonimine, Napqi

Description

Stability Air Sensitive, Light Sensitive, Moisture Sensitive, Temperature Sensitive
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)

• Brand: TRC

Chemical properties

• Molecular weight: 149.15
• Formula: C₈H₇NO₂
• Color/Form: Yellow To Orange
• InChI: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
• InChI key: InChIKey=URNSECGXFRDEDC-UHFFFAOYSA-N
• SMILES: CC(=O)N=C1C=CC(=O)C=C1