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
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
form
solid
Quality Level
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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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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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
Gregg V Crichlow et al.
Biochemistry, 48(1), 132-139 (2008-12-19)
Macrophage migration inhibitory factor (MIF) is a secreted protein expressed in numerous cell types that counters the antiinflammatory effects of glucocorticoids and has been implicated in sepsis, cancer, and certain autoimmune diseases. Interestingly, the structure of MIF contains a catalytic
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