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:
Molecular Weight:
149.15
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
MDL number:
Form:
solid
InChI
1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
SMILES string
CC(=O)\N=C1\C=CC(=O)C=C1
InChI key
URNSECGXFRDEDC-UHFFFAOYSA-N
form
solid
storage temp.
−70°C
Quality Level
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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
Disclaimer
air, moisture and light sensitive
Other Notes
Acetaminophen metabolite that reacts with serum proteins.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Jeffrey L Woodhead et al.
The Journal of pharmacology and experimental therapeutics, 342(2), 529-540 (2012-05-18)
N-acetylcysteine (NAC) is the treatment of choice for acetaminophen poisoning; standard 72-h oral or 21-h intravenous protocols are most frequently used. There is controversy regarding which protocol is optimal and whether the full treatment course is always necessary. It would
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
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
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
Shingo Arakawa et al.
The Journal of toxicological sciences, 37(3), 595-605 (2012-06-13)
We investigated the role of glutathione S-transferases Mu 1 (GSTM1) in acetaminophen (APAP)-induced hepatotoxicity using Gstm1-null mice. A single oral administration of APAP resulted in a marked increase in plasma alanine aminotransferase accompanied by hepatocyte necrosis 24 hr after administration
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