Acetimidoquinone

Title: Acetimidoquinone
CAS Registry Number: 50700-49-7
CAS Name: N-(4-oxo-2,5-cyclohexadien-1-ylidene)acetamide
Additional Names: N-acetyl-p-benzoquinonimine; N-acetylimidoquinone; NAPQI
Molecular Formula: C8H7NO2
Molecular Weight: 149.15
Percent Composition: C 64.42%, H 4.73%, N 9.39%, O 21.45%
Literature References: Proposed "ultimate" toxic metabolite of acetaminophen, q.v. Initially prepared by oxidation of acetaminophen with lead tetraacetate and characterized as a Diels-Alder adduct: I. C. Calder et al., J. Med. Chem. 16, 499 (1973). Electrochemical generation in buffer: D. J. Miner, P. T. Kissinger, Biochem. Pharmacol. 28, 3285 (1979). Synthesis in stable benzene soln and reactivity: I. A. Blair et al., Tetrahedron Lett. 21, 4947 (1980). Prepn in cryst form, decomposition kinetics, preliminary toxicological studies: D. C. Dahlin, S. D. Nelson, J. Med. Chem. 25, 885 (1982). Microsomal reactivity study: G. B. Corcoran, Adv. Exp. Med. Biol. 136B, 1085 (1982). Review of acetaminophen-induced hepatotoxicity: J. A. Hinson et al., Life Sci. 29, 107-116 (1981).
Properties: Yellow cubic cryst, mp 74-75°. Sublimes at 45-50° (0.07 mm Hg). uv max (n-hexane): 263, 376 nm (e 3.3´104, 1.6´102 M-1 cm-1). LD50 i.p. in male BALB/c mice: 20 mg/kg (Dahlin, Nelson).
Melting point: mp 74-75°
Absorption maximum: uv max (n-hexane): 263, 376 nm (e 3.3´104, 1.6´102 M-1 cm-1)
Toxicity data: LD50 i.p. in male BALB/c mice: 20 mg/kg (Dahlin, Nelson)
Acetoacetanilide Acetoacetic Acid Acetobromglucose Acetochlor Acetohexamide