Molecular structure of N-Acetyl-4-benzoquinone Imine, CAS Number: 50700-49-7
N-Acetyl-4-benzoquinone Imine (CAS 50700-49-7)
See product citations (2)
Alternate Names:
NAPQI; 4-(Acetylimino)-2,5-cyclohexadien-1-one; Acetimidoquinone
Application:
N-Acetyl-4-benzoquinone Imine is a toxic metabolite of Acetaminophen
CAS Number:
50700-49-7
Purity:
≥95%
Molecular Weight:
149.15
Molecular Formula:
C8H7NO2
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.
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SDS & Certificate of Analysis
N-Acetyl-4-benzoquinone Imine, or Acetimidoquinone (AIQ), is a toxic metabolite of Acetaminophen, which is known to react with serum proteins. It functions as an antioxidant, a chelating agent, and an inhibitor of enzymes, such as cytochrome P450 and DNA polymerase. On the other hand, it may act to increase the activity of detoxifying enzymes, such as glutathione S-transferase. N-Acetyl-4-benzoquinone Imine finds many applications in scientific research. For example, it is used in the synthesis of antibiotics, antifungal agents, anti-inflammatory agents, dyes, agrochemicals, proteins, enzymes, and hormones. It is also employed in the study of the structure and function of proteins, enzymes, and hormones.
N-Acetyl-4-benzoquinone Imine (CAS 50700-49-7) References
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- Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine. | Bedner, M. and MacCrehan, WA. 2006. Environ Sci Technol. 40: 516-22. PMID: 16468397
- On the chemistry of the reaction between N-acetylcysteine and 4-[(4-ethoxyphenyl)imino]-2,5-cyclohexadien-1-one, a 4-ethoxyaniline metabolite formed during peroxidase reactions. | Lindqvist, T., et al. 1991. Chem Res Toxicol. 4: 489-96. PMID: 1912338
- Early loss of large genomic DNA in vivo with accumulation of Ca2+ in the nucleus during acetaminophen-induced liver injury. | Ray, SD., et al. 1990. Toxicol Appl Pharmacol. 106: 346-51. PMID: 2256122
- Glutathione disulfide formation and oxidant stress during acetaminophen-induced hepatotoxicity in mice in vivo: the protective effect of allopurinol. | Jaeschke, H. 1990. J Pharmacol Exp Ther. 255: 935-41. PMID: 2262912
- Integrated digital microfluidic platform for voltammetric analysis. | Dryden, MD., et al. 2013. Anal Chem. 85: 8809-16. PMID: 24001207
- Formation of 4-aminophenoxyl free radical from the acetaminophen metabolite N-acetyl-p-benzoquinone imine. | Fischer, V., et al. 1985. J Biol Chem. 260: 11446-50. PMID: 2995335
- Comparative cytotoxic effects of N-acetyl-p-benzoquinone imine and two dimethylated analogues. | Rundgren, M., et al. 1988. Mol Pharmacol. 34: 566-72. PMID: 3173335
- PiTMaP: A New Analytical Platform for High-Throughput Direct Metabolome Analysis by Probe Electrospray Ionization/Tandem Mass Spectrometry Using an R Software-Based Data Pipeline. | Zaitsu, K., et al. 2020. Anal Chem. 92: 8514-8522. PMID: 32375466
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- Antioxidant and Prooxidant Effects of Thymoquinone and Its Hydroquinone Metabolite. | Mizuno, M. and Fukuhara, K. 2022. Biol Pharm Bull. 45: 1389-1393. PMID: 36047210
- Reactions of N-acetyl-p-benzoquinone imine with reduced glutathione, acetaminophen, and NADPH. | Potter, DW. and Hinson, JA. 1986. Mol Pharmacol. 30: 33-41. PMID: 3724743
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- Mechanisms of N-acetyl-p-benzoquinone imine cytotoxicity. | Albano, E., et al. 1985. Mol Pharmacol. 28: 306-11. PMID: 4033631
- Reduction and glutathione conjugation reactions of N-acetyl-p-benzoquinone imine and two dimethylated analogues. | Rosen, GM., et al. 1984. Mol Pharmacol. 25: 151-7. PMID: 6323948
Ordering Information
| Product Name | Catalog # | UNIT | Price | Qty | FAVORITES | |
N-Acetyl-4-benzoquinone Imine, 1 mg | sc-212083 | 1 mg | $243.00 | |||
N-Acetyl-4-benzoquinone Imine, 2 mg | sc-212083A | 2 mg | $426.00 | |||
N-Acetyl-4-benzoquinone Imine, 5 mg | sc-212083B | 5 mg | $634.00 | |||
N-Acetyl-4-benzoquinone Imine, 10 mg | sc-212083C | 10 mg | $1093.00 | |||
N-Acetyl-4-benzoquinone Imine, 25 mg | sc-212083D | 25 mg | $1987.00 |