N-ACETYL-4-BENZOQUINONE IMINE

Synonym(s):N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide;N-Acetyl-p-benzo-quinoneimine;NAPQI

CAS NO.：50700-49-7
Empirical Formula: C8H7NO2
Molecular Weight: 149.15
MDL number: MFCD00078909
SAFETY DATA SHEET (SDS)
Update Date: 2026-05-27 22:52:50

N-ACETYL-4-BENZOQUINONE IMINE Structural

What is N-ACETYL-4-BENZOQUINONE IMINE?

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. 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.

Chemical properties

Yellow Crystalline Solid

The Uses of N-ACETYL-4-BENZOQUINONE IMINE

A toxic metabolite of Acetaminophen, which reacts with serum proteins

The Uses of N-ACETYL-4-BENZOQUINONE IMINE

A toxic metabolite of Acetaminophen (A161220), which reacts with serum proteins.

The Uses of N-ACETYL-4-BENZOQUINONE IMINE

Reactant involved in:• ;Redox reactions1• ;Hydrohalogenation2• ;pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs3• ;Mediation of acetaminophen hepatotoxicity4• ;Studies to identify the utility of acetaminophen for treating autoimmune disorders5

What are the applications of Application

N-Acetyl-4-benzoquinone Imine is a toxic metabolite of Acetaminophen

Definition

ChEBI: N-acetyl-1,4-benzoquinone imine is a quinone imine and a ketoimine. It is functionally related to a 1,4-benzoquinone imine.

Properties of N-ACETYL-4-BENZOQUINONE IMINE

Melting point:	74-75
Boiling point:	255.6±43.0 °C(Predicted)
Density	1.13±0.1 g/cm3(Predicted)
storage temp.	-70°C
solubility	Chloroform (Slightly, Sonicated), DMSO (Slightly)
form	Solid
pka	-3.37±0.20(Predicted)
color	Pale Yellow to Very Dark Red
Stability:	Temperature, Moisture, Light, and Oxygen Sensitive
CAS DataBase Reference	50700-49-7

Safety information for N-ACETYL-4-BENZOQUINONE IMINE

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P362:Take off contaminated clothing and wash before reuse. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention.