Acetaminophen
Title: Acetaminophen
CAS Registry Number: 103-90-2
CAS Name: N-(4-Hydroxyphenyl)acetamide
Additional Names: 4¢-hydroxyacetanilide; p-hydroxyacetanilide; p-acetamidophenol; p-acetaminophenol; p-acetylaminophenol; N-acetyl-p-aminophenol; paracetamol
Trademarks: Acamol (Teva); Alpiny (SS Pharm.); Anaflon (GSK); Anhiba (Hokuriku); Apamide (Bayer); Ben-u-ron (Bene-Arzneimittel); Calpol (Pfizer); Captin (Krewel); Dafalgan (UPSA); Datril (BMS); Dirox (Gramon); Disprol (Reckitt Benckiser); Doliprane (Thžaplix); Dolprone (Bottu); Enelfa (Dolorgiet); Gelocatil (Gelos); Hedex (GSK); Momentum (Wyeth); Ortensan (Cimex); Panadol (GSK); Panaleve (Pinewood); Panodil (GSK); Paraspen (Pfizer); Pasolind N (Stada); Tempra (BMS); Tylenol (McNeil); Valadol (BMS)
Molecular Formula: C8H9NO2
Molecular Weight: 151.16
Percent Composition: C 63.57%, H 6.00%, N 9.27%, O 21.17%
Literature References: Prepn from p-nitrophenol: Morse, Ber. 11, 232 (1878); Tingle, Williams, Am. Chem. J. 37, 63 (1907); from p-aminophenol: Lumière et al., Bull. Soc. Chim. Fr. [3] 33, 785 (1905); Fierz-David, Kuster, Helv. Chim. Acta 22, 94 (1939); Wilbert, De Angelis, US 2998450 (1961 to Warner-Lambert); Bergmann, DE 453577; Chem. Zentralbl. 1928, I, 2663; Frdl. 16, 238; from p-hydroxyacetophenone hydrazone: Pearson et al., J. Am. Chem. Soc. 75, 5907 (1953). Toxicity data: G. A. Starmer et al., Toxicol. Appl. Pharmacol. 19, 20 (1971); D. C. Dahlin, S. D. Nelson, J. Med. Chem. 25, 885 (1982). Evaluation of renal effects: D. P. Sandler et al., N. Engl. J. Med. 320, 1238 (1989). Comprehensive description: J. E. Fairbrother, Anal. Profiles Drug Subs. 3, 1-109 (1974). Review of pharmacology: B. Ameer, D. J. Greenblatt, Ann. Intern. Med. 87, 202-209 (1977). Review of acetaminophen-induced hepatotoxicity: J. A. Hinson, Rev. Biochem. Toxicol. 2, 103-129 (1980); idem, Life Sci. 29, 107-116 (1981); and proposed protective agents: M. Davis, Semin. Liver Dis. 6, 138-147 (1986). For proposed toxic metabolite see Acetimidoquinone.
Properties: Large monoclinic prisms from water, mp 169-170.5°. d421 1.293. uv max (ethanol): 250 nm (e 13800). Very slightly sol in cold water, considerably more sol in hot water. Sol in methanol, ethanol, dimethylformamide, ethylene dichloride, acetone, ethyl acetate. Slightly sol in ether. Practically insol in petr ether, pentane, benzene. LD50 in mice (mg/kg): 338 orally (Starmer), 500 i.p. (Dahlin, Nelson).
Melting point: mp 169-170.5°
Absorption maximum: uv max (ethanol): 250 nm (e 13800)
Density: d421 1.293
Toxicity data: LD50 in mice (mg/kg): 338 orally (Starmer), 500 i.p. (Dahlin, Nelson)
Use: Manuf azo dyes, photographic chemicals.
Therap-Cat: Analgesic; antipyretic.
Keywords: Analgesic (Non-Narcotic); Antipyretic.

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