A reactive CYP450 metabolite of acetaminophen
Related Products
Parent Compound(s)
10024Acetaminophen
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N-Acetyl-4-benzoquinone imine

Item No. 16115

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(4-oxo-2,5-cyclohexadien-1-ylidene)-acetamide
CAS Number
50700-49-7
Synonyms
  • NAPQI
  • N-Acetyl-p-benzoquinonimine
Molecular Formula
C8H7NO2
Formula Weight
149.2
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Chloroform: 1 mg/ml*Chloroform/Ethyl Acetate (1:1): 1 mg/mlEther: 1 mg/mlEthyl Acetate: 1 mg/ml
λmax
260 nm
SMILES
O=C(C=C/1)C=CC1=N\C(C)=O
InChi Code
InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
InChi Key
URNSECGXFRDEDC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $129

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    1 mg

    $245

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    5 mg

    $1,016

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    Product Description

    N-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses.1 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.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Qiu, Y., Benet, L.Z., and Burlingame, A.L. Identification of the hepatic protein targets of reactive metabolites of acetaminophen in vivo in mice using two-dimensional gel electrophoresis and mass spectrometry. The Journal of Biological Chemisty 273(28), 17940-17953 (1998).