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Merck
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Key Documents

Altri documenti

A7300

Sigma-Aldrich

N-Acetylbenzoquinoneimine

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H7NO2
Numero CAS:
50700-49-7
Peso molecolare:
149.15
Numero MDL:
MFCD00078909
Codice UNSPSC:
12352100
ID PubChem:
57653880
NACRES:
NA.22

Forma fisica

solid

Livello qualitativo

100

Temperatura di conservazione

−70°C

Stringa SMILE

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
URNSECGXFRDEDC-UHFFFAOYSA-N

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Categorie correlate

Applicazioni

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

Altre note

Acetaminophen metabolite that reacts with serum proteins.

Avvertenza

air, moisture and light sensitive

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Acetaminofene British Pharmacopoeia (BP) Reference Standard

BP371

Acetaminofene

Sigma-Aldrich

Sigma-Aldrich

270733

Acqua

Acetaminofene analytical standard

Sigma-Aldrich

A3035

Acetaminofene

Timestrip Plus™ -20 °C

Supelco

06693

Timestrip Plus™ -20 °C

Acetaminofene BioXtra, ≥99.0%

Sigma-Aldrich

A7085

Acetaminofene

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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