CAS Number50700-49-7
SynonymsAcetimidoquinone; N-Acetyl-1,4-benzoquinone imine; N-Acetyl-p-benzoquinonimine; N-(4-Oxo-2,5-cyclohexadien-1-ylidene)acetamide; N-Acetyl-P-benzoquinoneimine; N-Acetyl-4-benzoquinone Imine; N-acetyl-4-benzoquinoneimine; 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
Molecular FormulaC8H7NO2
Molecular Weight149.15
Density1.1±0.1 g/cm3
Boiling Point255.6±43.0 °C at 760 mmHg
Melting Point74-75ºC
Appearancesolid
| Chemical & Physical Properties | |
|---|---|
| CAS Number | 50700-49-7 |
| Catalog No. | 2A-9084484 |
| Chinese Name | N-乙酰苯醌亚胺 |
| Synonyms | Acetimidoquinone; N-Acetyl-1,4-benzoquinone imine; N-Acetyl-p-benzoquinonimine; N-(4-Oxo-2,5-cyclohexadien-1-ylidene)acetamide; N-Acetyl-P-benzoquinoneimine; N-Acetyl-4-benzoquinone Imine; N-acetyl-4-benzoquinoneimine; 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 |
| Molecular Formula | C8H7NO2 |
| Molecular Weight | 149.15 |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 255.6±43.0 °C at 760 mmHg |
| Melting Point | 74-75ºC |
| Appearance | solid |
| Storage Condition | -20°C |
| Application | NAPQI is a toxic metabolite of acetaminophen. NAPQI is also an inhibitor of enzymes in the vitamin K cycle. NAPQI rapidly detoxifies through glutathione (GSH), but in the absence of GSH, excess NAPQI |
| HTC | 2924299090 |
| PubChem ID | 57653880 |
| MDL Number | MFCD00078909 |
| SMILES | 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 |
| NACRES Code | NA.22 |
| UNSPSC | 12352100 |
| MSDS | msds/84484_1_50700_49_7.pdf |
| Use of | 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]. Properties Articles28 Name N-acetyl-1,4-benzoquinone imine Synonym More Synonyms N-Acetylimidoquinone 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 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 Molecular Formula C8H7NO2 Exact Mass 149.047684 PSA 46.50000 Index of Refraction 1.545 InChIKey URNSECGXFRDEDC-UHFFFAOYSA-N Toxicological Information CHEMICAL IDENTIFICATION RTECS NUMBER : CHEMICAL NAME : Acetamide, N-(4-oxo-2,5-cyclohexadien-1-ylidene)- CAS REGISTRY NUMBER : 50700-49-7 LAST UPDATED : DATA ITEMS CITED : MOLECULAR FORMULA : C8-H7-N-O2 MOLECULAR WEIGHT : 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 : 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 4-Acetamidophenol CAS#:103-90-2 N-Acetylimidoquinone CAS#:50700-49-7 Literature: Bessems; Te Koppele; Van Dijk; Van Stee; Commandeur; Vermeulen Xenobiotica, 1996 , vol. 26, # 6 p. 647 - 666 N-(pivaloyloxy)... CAS#:99512-61-5 CAS#:67-56-1 N-Acetylimidoquinone CAS#:50700-49-7 Literature: Novak, Michael; Pelecanou, Maria; Pollack, Lee Journal of the American Chemical Society, 1986 , vol. 108, # 1 p. 112 - 120 N-(pivaloyloxy)... CAS#:99512-61-5 4-Acetamidophenol CAS#:103-90-2 N-(3-Chloro-4-h... CAS#:3964-54-3 N-Acetylimidoquinone CAS#:50700-49-7 Literature: Novak, Michael; Pelecanou, Maria; Pollack, Lee Journal of the American Chemical Society, 1986 , vol. 108, # 1 p. 112 - 120 Precursor & DownStream Precursor 4 CAS#:103-90-2 4-Acetamidophenol CAS#:63975-21-3 N-hydroxyacetam... CAS#:696-33-3 Benzene, iodyl CAS#:123-30-8 4-Aminophenol DownStream 6 CAS#:37398-23-5 S-Methyl-3-thio... CAS#:103-90-2 4-Acetamidophenol CAS#:3964-54-3 N-(3-Chloro-4-h... CAS#:106-51-4 1,4-Benzoquinone |
| Tax Rebate | 13.0% |
| Supervision | None. MFN tariff: 6.5%. Ordinary tariff: 30.0% |
| Transport Info | Product name: 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% |
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