Nacetylpbenzoquinone

Nacetylpbenzoquinone is not a recognized IUPAC name for a defined compound. The closest well-documented term is N-acetyl-p-benzoquinone imine (NAPQI), a reactive metabolite formed during the metabolism of acetaminophen (paracetamol).

NAPQI is generated primarily by cytochrome P450 enzymes, notably CYP2E1, from the acetaminophen molecule. It is an electrophilic quinone imine that can react with nucleophiles, particularly thiol groups on glutathione and cysteine residues in proteins. Under normal conditions, hepatic glutathione conjugates NAPQI, facilitating its detoxification and clearance.

In acetaminophen overdose or when glutathione stores are depleted, NAPQI accumulation leads to covalent modification of cellular proteins, oxidative stress, mitochondrial dysfunction, and hepatocellular injury. Clinically, NAPQI toxicity is the principal mechanism of acetaminophen-induced liver failure. Treatment with N-acetylcysteine replenishes glutathione levels and provides a nucleophilic substrate that helps neutralize NAPQI.

NAPQI is primarily discussed in toxicology and pharmacology contexts rather than as a standalone reagent in routine chemistry. If a different compound was intended by "Nacetylpbenzoquinone," further clarification of the name or structure would be helpful.