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A7300

Sigma-Aldrich

N-Acetylbenzoquinoneimine

Sinónimos:

N-(4-oxo-1-cyclohexa-2,5-dienylidene)acetamide, N-Acetyl-p-benzo-quinone imine, NAPQI

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About This Item

Fórmula empírica (notación de Hill):
C8H7NO2
Número de CAS:
50700-49-7
Peso molecular:
149.15
MDL number:
MFCD00078909
UNSPSC Code:
12352100
PubChem Substance ID:
57653880
NACRES:
NA.22

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

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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.

Caution

air, moisture and light sensitive

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Xiang Ma et al.
Bioconjugate chemistry, 21(1), 46-55 (2009-12-05)
The purpose of our paper is to develop and validate a fluorescence-based mouse liver microsomal (MLM) assay in screening pharmaceutical reactive metabolites (RMs) using a glutathione (GSH)-conjugated 96-well plate. Poly(2-hydroxyethylmethacrylate) (pHEMA) polymeric membrane was coated on 96-well plates to provide
Hannah Simon et al.
Analytical chemistry, 84(20), 8777-8782 (2012-09-14)
During the development of new materials demonstrating biological activity, prediction and identification of reactive intermediates generated in the course of drug metabolism in the human liver is of great importance. We present a rapid and purely instrumental method for the
Carmen Flores-Pérez et al.
Biomedical chromatography : BMC, 25(7), 760-766 (2010-09-30)
The aim of the present study was to develop a simple, selective and reliable method to quantify acetaminophen and its toxic metabolite N-acetyl-p-benzoquinoneimine (NAPQI) for pediatric studies using 100 µL plasma samples, by reverse-phase HPLC and UV detection. The assay was
Rosalind E Jenkins et al.
Proteomics, 8(2), 301-315 (2008-01-19)
Chemically reactive metabolites (CRMs) are thought to be responsible for a number of adverse drug reactions through modification of critical proteins. Methods that defined the chemistry of protein modification at an early stage would provide invaluable tools for drug safety
Kiyoshi Fukuhara et al.
Drug metabolism and pharmacokinetics, 26(4), 399-406 (2011-06-15)
The widely used analgesic-antipyretic drug acetaminophen (APAP) is known to cause serious liver necrosis at high doses in man and experimental animals. For studies of toxic processes, 1H NMR spectroscopy of biofluids allows monitoring of endogenous metabolite profiles that alter
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