Basic information
- CAS
50700-49-7- Standard SMILES
CC(=O)N=C1C=CC(=O)C=C1- InChIKey
URNSECGXFRDEDC-UHFFFAOYSA-N- Molecular formula
- C8H7NO2
- Average molar mass
- 149.15 g/mol
- Monoisotopic mass
- 149.04767847
Overview
N-acetyl-1,4-benzoquinone imine is a quinone imine and a ketoimine. It is functionally related to a 1,4-benzoquinone imine.
Names & identifiers
- Preferred name
- Acetimidoquinone
- IUPAC
- N-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide
- English name
- N-ACETYL-4-BENZOQUINONE IMINE
- Molecular formula
- C8H7NO2
- Molecular weight
- 149.15
Names & synonyms
Napqi50700-49-7AcetimidoquinoneN-acetyl-4-benzoquinone imineN-Acetyl-p-benzoquinone imineN-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamideN-Acetyl-4-benzoquinoneimineN-Acetyl-p-benzoquinoneN-Acetyl-P-benzoquinoneimineN-Acetyl-p-quinoniminen-acetyl-p-benzoquinonimineCCRIS 5789
Show more names
N-AcetylimidoquinoneChebi:29132synthesis-28N-ACETYL-PARA-QUINONEIMINEN-ACETYLBENZOQUINONE-IMINE
Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)-G6S9BN13TIN-(4-Oxo-2,5-cyclohexadienylidene)acetamideBRN 24356212,5-Cyclohexadien-1-one, 4-acetylimino-DTXSID20198756N-(4-Oxo-2,5-cyclohexadien-1-ylidene)acetamideACETIMIDOQUINONE [MI]
Database identifiers
- CAS
50700-49-7- PubChem CID
- 39763
- DTXSID
DTXSID20198756- ChEMBL
CHEMBL33232
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 46.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 266
Experimental & physicochemical properties
DrugsPharmaceuticals -> Metabolite of Paracetamol
Physicochemical properties
- Melting point
- 74 · 74-75
- Boiling point
- 255.6 · 255.6±43.0 °C(Predicted)
- Density
- 1.13 · 1.13±0.1 g/cm3(Predicted)
- storage temp.
- -70 °C · -70°C
- solubility
- Chloroform (Slightly, Sonicated), DMSO (Slightly)
- form
- Solid
- pka
- -3.37 · -3.37±0.20(Predicted)
- color
- Pale Yellow to Very Dark Red
- Stability
- Temperature, Moisture, Light, and Oxygen Sensitive
- InChI
- 1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
- InChIKey
- URNSECGXFRDEDC-UHFFFAOYSA-N
- SMILES
- CC(=O)\N=C1\C=CC(=O)C=C1
- CAS DataBase Reference
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- AC6960000
- hs_code
- 2902110000
- Toxicity
- LD50 i.p. in male BALB/c mice: 20 mg/kg (Dahlin, Nelson)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Chemistry & industry
Pharmacology
Metabolism/MetabolitesN-Acetyl-p-benzoquinone is a known human metabolite of acetaminophen.
Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysAcetaminophen Metabolism Pathway
Applications
DescriptionN-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses. At therapeutic doses of acetaminophen, NAPQI is inactivated by conjugation with glutathione. However, following toxic doses of acetaminophen, available liver reserves of glutathione are quickly depleted due to clearance of excess NAPQI, which enables hepatic proteins to become covalently modified by reactive metabolites and eventually results in hepatocyte necrosis.
UsesA toxic metabolite of Acetaminophen, which reacts with serum proteins
UsesA toxic metabolite of Acetaminophen (A161220), which reacts with serum proteins.
UsesReactant involved in:• ;Redox reactions1• ;Hydrohalogenation2• ;pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs3• ;Mediation of acetaminophen hepatotoxicity4• ;Studies to identify the utility of acetaminophen for treating autoimmune disorders5
UsesN-Acetyl-4-benzoquinone imine (NAPQI) is a cytochrome P450 3A4 and 2E1 metabolite of acetaminophen that can be toxic to the liver when acetaminophen is consumed in large doses. At therapeutic doses of acetaminophen, NAPQI is inactivated by conjugation with glutathione. However, following toxic doses of acetaminophen, available liver reserves of glutathione are quickly depleted due to clearance of excess NAPQI, which enables hepatic proteins to become covalently modified by reactive metabolites and eventually results in hepatocyte necrosis.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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