N-Acetylimidoquinone

Names

[ Name ]:
N-Acetylimidoquinone

[Synonym ]:
Acetimidoquinone
N-Acetyl-1,4-benzoquinone imine
N-Acetyl-p-benzoquinonimine
p-benzoquinonimine, N-acetyl-
N-(4-Oxo-2,5-cyclohexadien-1-ylidene)acetamide
N-Acetyl-P-benzoquinoneimine
N-Acetyl-4-benzoquinone Imine
N-acetyl-4-benzoquinoneimine
Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)-
N-(4-Oxocyclohexa-2,5-dien-1-ylidene)acetamide
NAPQI
N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide,N-Acetyl-p-benzo-quinoneimine,NAPQI

Biological Activity

[Description]:

NAPQI is the toxic metabolite of Paracetamol. NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI is rapidly detoxified by glutathione (GSH), but in situations of GSH deficiency, excess NAPQI reacts with cysteine residues in proteins, causing cell death and toxicity in the liver[1][2].

[Related Catalog]:

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[References]

[1]. Jiang D, et al. Organ-Specific Screening for Protein Damage Using Magnetic Bead Bioreactors and LC-MS/MS. Anal Chem. 2020 Apr 7;92(7):5337-5345.

[2]. Thijssen HH, et al. Paracetamol (acetaminophen) warfarin interaction: NAPQI, the toxic metabolite of paracetamol, is an inhibitor of enzymes in the vitamin K cycle. Thromb Haemost. 2004 Oct;92(4):797-802.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
255.6±43.0 °C at 760 mmHg

[ Melting Point ]:
74-75ºC

[ Molecular Formula ]:
C₈H₇NO₂

[ Molecular Weight ]:
149.147

[ Flash Point ]:
101.6±33.5 °C

[ Exact Mass ]:
149.047684

[ PSA ]:
46.50000

[ LogP ]:
0.38

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.545

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC6960000

CHEMICAL NAME :: Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)-

CAS REGISTRY NUMBER :: 50700-49-7

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C8-H7-N-O2

MOLECULAR WEIGHT :: 149.16

WISWESSER LINE NOTATION :: L6V DYJ DUNV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 20 mg/kg

TOXIC EFFECTS :: Blood - change in clotting factors

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 25,885,1982

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
AC6960000

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Targeting mitochondria with methylene blue protects mice against acetaminophen-induced liver injury.

Hepatology 61(1) , 326-36, (2015)

Acetaminophen (APAP) overdose is a frequent cause of drug-induced liver injury and the most frequent cause of acute liver failure in the Western world. Previous studies with mouse models have revealed...

Monitoring paracetamol metabolism after single and repeated administration in pediatric patients with neoplastic diseases.

Int. J. Clin. Pharmacol. Ther. 45(9) , 496-503, (2007)

Paracetamol (PCM) is frequently used in pediatric patients with neoplastic disease. It is metabolized mainly by conjugation, but at therapeutic concentrations, a small fraction of the drug undergoes o...

Use of a systems model of drug-induced liver injury (DILIsym®) to elucidate the mechanistic differences between acetaminophen and its less-toxic isomer, AMAP, in mice

Toxicol. Lett. 226(2) , 163-72, (2014)

Acetaminophen (APAP) has been used as a probe drug to investigate drug-induced liver injury (DILI). In mice, 3′-hydroxyacetanilide (AMAP), a less-toxic isomer of APAP, has also been studied as a negat...