N-ACETYL-4-BENZOQUINONE IMINE Chemical Properties

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

WGK Germany 

3

RTECS 

AC6960000

HS Code 

2902110000

Toxicity

LD50 i.p. in male BALB/c mice: 20 mg/kg (Dahlin, Nelson)

MSDS

• Language:English Provider:SigmaAldrich

N-ACETYL-4-BENZOQUINONE IMINE Usage And Synthesis

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

Uses

A toxic metabolite of Acetaminophen, which reacts with serum proteins

Uses

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

Uses

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

Uses

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.

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.

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