N-Acetyl-4-benzoquinone Imine | B2306

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.

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.

B2306 | N-Acetyl-4-benzoquinone Imine DataSheet

Alternate Name/Synonyms: N-(4-oxo-2,5-cyclohexadien-1-ylidene)-acetamide; NAPQI

Appearance: Pale yellow to dark brown solid

Formulation: N/A

CAS Number: 50700-49-7

Structure Available?: Yes

Peptide sequence: N/A

Salt Form: No

Molecular Formula: C₈H₇NO₂

Molecular Weight: 149.2

Cell-Permeable?: Yes

Purity: ≥90% by HPLC

Solubilities: CHCl3 (1 mg/ml) or EtOAc (1 mg/ml)

Handling: Protect from air and light

Country of Origin: USA

Tag Line: A toxic metabolite of Acetaminophen

MDL Number: MFCD00078909

PubChem CID: 39763

SMILES: CC(=O)N=C1C=CC(=O)C=C1

InChi: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3

InChi Key: URNSECGXFRDEDC-UHFFFAOYSA-N