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NAPQI

CAT: 0804-HY-W017464-01Size: 1 mgDry Ice: YesHazardous: No
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CAT#:0804-HY-W017464-01Size:1 mg
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Description
NAPQI is the toxic metabolite of Acetaminophen. 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].
CAS Number
50700-49-7
Product Name Alternative
N-Acetyl-4-benzoquinone Imine
UNSPSC
12352211
Hazard Statement
H315, H319
Target
Drug Metabolite; Endogenous Metabolite
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-protein/nucleotide metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/napqi.html
Purity
99.67
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
CC(/N=C1C=CC(C=C\1)=O)=O
Molecular Formula
C8H7NO2
Molecular Weight
149.15
Precautions
H315, H319
References & Citations
[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.|[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.|[3]Walker V, et al. The acetaminophen metabolite N-acetyl-p-benzoquinone imine (NAPQI) inhibits glutathione synthetase in vitro; a clue to the mechanism of 5-oxoprolinuric acidosis? Xenobiotica. 2017 Feb;47 (2) :164-175.|[4]Kalinec GM, et al. Acetaminophen and NAPQI are toxic to auditory cells via oxidative and endoplasmic reticulum stress-dependent pathways. Hear Res. 2014 Jul;313:26-37.
Shipping Conditions
Dry Ice
Storage Conditions
-80°C, protect from light, stored under nitrogen
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
Human Endogenous Metabolite

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