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Merck

A7300

N-Acetylbenzoquinoneimine

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H7NO2
CAS Number:
50700-49-7
Molecular Weight:
149.15
NACRES:
NA.22
PubChem Substance ID:
57653880
UNSPSC Code:
12352100
MDL number:
MFCD00078909
Form:
solid

Key Documents

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form

solid

Quality Level

100

storage temp.

−70°C

SMILES string

CC(=O)\N=C1\C=CC(=O)C=C1

InChI

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

InChI key

URNSECGXFRDEDC-UHFFFAOYSA-N

Related Categories

Application

Reactant involved in:
  • Redox reactions
  • Hydrohalogenation
  • pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs
  • Mediation of acetaminophen hepatotoxicity
  • Studies to identify the utility of acetaminophen for treating autoimmune disorders

Other Notes

Acetaminophen metabolite that reacts with serum proteins.

Disclaimer

air, moisture and light sensitive

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A7300-BULK: + A7300-5MG-PW: + A7300-1MG: + A7300-5MG: + A7300-1MG-PW: + A7300-250UG: + A7300-VAR:

jan

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Certificates of Analysis (COA)

Lot/Batch Number
118K1255
128K0967
103K1216
117K1179
127K1351

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Angela S Burke et al.
Chemical research in toxicology, 23(7), 1286-1292 (2010-06-29)
Acetaminophen (APAP) toxicity in primary mouse hepatocytes occurs in two phases. The initial phase (0-2 h) occurs with metabolism to N-acetyl-p-benzoquinoneimine which depletes glutathione, and covalently binds to proteins, but little toxicity is observed. Subsequent washing of hepatocytes to remove
Laura P James et al.
Drug metabolism and disposition: the biological fate of chemicals, 37(8), 1779-1784 (2009-05-15)
Acetaminophen (APAP)-induced liver toxicity occurs with formation of APAP-protein adducts. These adducts are formed by hepatic metabolism of APAP to N-acetyl-p-benzoquinone imine, which covalently binds to hepatic proteins as 3-(cystein-S-yl)-APAP adducts. Adducts are released into blood during hepatocyte lysis. We
Amaresh Kumar Sahoo et al.
Nanoscale, 3(10), 4226-4233 (2011-09-08)
Herein, we report the generation of a composite comprised of p-hydroxyacetanilide dimer and Ag nanoparticles (NPs) by reaction of AgNO(3) and p-hydroxyacetanilide. The formation of the composite was established by UV-vis, FTIR and NMR spectroscopy, transmission electron microscopy and X-ray
Hui Ting Chng et al.
Journal of biomolecular screening, 17(7), 974-986 (2012-05-31)
The zebrafish model has been increasingly explored as an alternative model for toxicity screening of pharmaceutical drugs. However, little is understood about the bioactivation of drug to reactive metabolite and phase I and II metabolism of chemical in zebrafish as
Cross-linking of protein molecules by the reactive metabolite of acetaminophen, N-acetyl-p-benzoquinone imine, and related quinoid compounds.
A J Streeter et al.
Advances in experimental medicine and biology, 197, 727-737 (1986-01-01)
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