N-Acetyl-4-benzoquinone imine

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Cat No: 16115

Biochemicals - Small Molecule Inhibitors

N-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses.{7361} At therapeutic doses of acetaminophen, NAPQI is inactivated by conju...

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Territorial Availability: Available through Bertin Technologies only in France

Synonyms:

N-(4-oxo-2,5-cyclohexadien-1-ylidene)-acetamide

Correlated keywords:

liver toxicity hepatotoxicity acetaminophen paracetamol cytochrome P450 oxidative stress glutathione biochemical CYP450 metabolism injury ox toxicology N-Acetyl-p-benzoquinonimine Acetimidoquinone N-Acetyl-1,4-benzoquinonimine N-acetylbenzoquinoneimine 3A4 2E1 CYP3A4 CYP2E1 metabolite conjugation hepatic protein hepatocyte necrosis ferroptosis

Product Overview:
N-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses.{7361} At therapeutic doses of acetaminophen, NAPQI is inactivated by conjugation with glutathione. However, following toxic doses of acetaminophen, available liver reserves of glutathione are quickly depleted due to clearance of excess NAPQI, which enables hepatic proteins to become covalently modified by reactive metabolites and eventually results in hepatocyte necrosis.{7361}

Size	500 µg
Shipping	dry ice
CAS Number	50700-49-7
Molecular Formula	C₈H₇NO₂
SMILES	O=C(C=C/1)C=CC1=N\C(C)=O
Molecular Weight	149,2
Formulation	A crystalline solid
Purity	≥90%
Custom Code	2922.19
UNSPSC code	12352100

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Cayman Chemical's mission is to help make research possible by supplying scientists worldwide with the basic research tools necessary for advancing human and animal health. Our utmost commitment to healthcare researchers is to offer the highest quality products with an affordable pricing policy.

Our scientists are experts in the synthesis, purification, and characterization of biochemicals ranging from small drug-like heterocycles to complex biolipids, fatty acids, and many others. We are also highly skilled in all aspects of assay and antibody development, protein expression, crystallization, and structure determination.

Over the past thirty years, Cayman developed a deep knowledge base in lipid biochemistry, including research involving the arachidonic acid cascade, inositol phosphates, and cannabinoids. This knowledge enabled the production of reagents of exceptional quality for cancer, oxidative injury, epigenetics, neuroscience, inflammation, metabolism, and many additional lines of research.

Our organic and analytical chemists specialize in the rapid development of manufacturing processes and analytical methods to carry out clinical and commercial GMP-API production. Pre-clinical drug discovery efforts are currently underway in the areas of bone restoration and repair, muscular dystrophy, oncology, and inflammation. A separate group of Ph.D.-level scientists are dedicated to offering Hit-to-Lead Discovery and Profiling Services for epigenetic targets. Our knowledgeable chemists can be contracted to perform complete sample analysis for analytes measured by the majority of our assays. We also offer a wide range of analytical services using LC-MS/MS, HPLC, GC, and many other techniques.

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ISO/IEC 17025:2005
ISO Guide 34:2009

Cayman is a leader in the field of emerging drugs of abuse, providing high-purity Schedule I-V Controlled Substances to federally-licensed laboratories and qualified academic research institutions for forensic analyses. We are certified by ACLASS Accreditation Services with dual accreditation to ISO/IEC 17025:2005 and ISO Guide 34:2009.