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[1][2].

Product Specifications

Product Name Alternative

N-Acetyl-4-benzoquinone Imine-d3

UNSPSC

12352211

Target

Drug Metabolite; Endogenous Metabolite; Isotope-Labeled Compounds

Related Pathways

Metabolic Enzyme/Protease; Others

Field of Research

Metabolic Disease

Smiles

O=C1C=C/C(C=C1)=N/C(C([2H])([2H])[2H])=O

Molecular Formula

C8H4D3NO2

Molecular Weight

152.17

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.