50700-49-7
Chemical Structure
NAPQI
Synonym(s): N-Acetyl-4-benzoquinone Imine
- CAS No.: 50700-49-7
- Formula:C8H7NO2
- Molecular Weight:149.15
IUPAC Name: N-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide
InChIKey: URNSECGXFRDEDC-UHFFFAOYSA-N
SMILES: CC(/N=C1C=CC(C=C\1)=O)=O
Biological Activity: NAPQI is the toxic metabolite of Acetaminophen (HY-66005). NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI is rapidly detoxified by glutathione (GSH), but in situations of GSH deficiency, excess NAPQI reacts with cysteine residues in proteins, causing cell death and toxicity in the liver[1][2].
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NAPQI | 98.0% | NAPQI is the toxic metabolite of Acetaminophen (HY-66005). NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI is rapidly detoxified by glutathione (GSH), but in situations of GSH deficiency, excess NAPQI reacts with cysteine residues in proteins, causing cell death and toxicity in the liver. | ||||||||||||||||||||
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NAPQI (Standard) | ≥98% | NAPQI (Standard) is the analytical standard of NAPQI (HY-W017464). This product is intended for research and analytical applications. NAPQI is the toxic metabolite of Acetaminophen (HY-66005). NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI is rapidly detoxified by glutathione (GSH), but in situations of GSH deficiency, excess NAPQI reacts with cysteine residues in proteins, causing cell death and toxicity in the liver. | ||||||||||||||||||||
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NAPQI-d3 | NAPQI-d3 (N-Acetyl-4-benzoquinone Imine-d3) is the deuterium labeled NAPQI (HY-W017464). NAPQI is the toxic metabolite of Acetaminophen (HY-66005). NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI is rapidly detoxified by glutathione (GSH), but in situations of GSH deficiency, excess NAPQI reacts with cysteine residues in proteins, causing cell death and toxicity in the liver. | |||||||||||||||||||||
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- [1]. Jiang D, et al. Organ-Specific Screening for Protein Damage Using Magnetic Bead Bioreactors and LC-MS/MS. Anal Chem. 2020 Apr 7;92(7):5337-5345. [Content Brief]
- [2]. Thijssen HH, et al. Paracetamol (acetaminophen) warfarin interaction: NAPQI, the toxic metabolite of paracetamol, is an inhibitor of enzymes in the vitamin K cycle. Thromb Haemost. 2004 Oct;92(4):797-802. [Content Brief]
Keywords
