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N-Acetyl-4-benzoquinone Imine

A toxic metabolite of Acetaminophen
Catalog #: B2306
SKU-Size Size Price Qty
B2306-1 1 mg
B2306-5 5 mg
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Product Details

Alternate Name N-(4-oxo-2,5-cyclohexadien-1-ylidene)-acetamide; NAPQI
Appearance Pale yellow to dark brown solid
CAS # 50700-49-7
Molecular Formula C₈H₇NO₂
Molecular Weight 149.2
Purity ≥90% by HPLC
Solubility CHCl3 (1 mg/ml) or EtOAc (1 mg/ml)
InChi InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
PubChem CID 39763
MDL Number MFCD00078909
Handling Protect from air and light
Storage Conditions -20°C
Shipping Conditions Gel Pack
USAGE For Research Use Only! Not For Use in Humans.


N-Acetyl-4-benzoquinone Imine (NAPQI) is a toxic cytochrome P450 3A4 and 2E1 metabolite of Acetaminophen. 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.

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