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NAPQI

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].

Product Specifications

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

Available Sizes

Frequently Asked Questions

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