Cinchophen
Title: Cinchophen
CAS Registry Number: 132-60-5
CAS Name: 2-Phenyl-4-quinolinecarboxylic acid
Additional Names: 2-phenylcinchoninic acid
Trademarks: Atophan (Warner-Chilcott); Quinophan; Phenoquin; Agotan; Artam; Alutyl; Cinconal; Vantyl; Viophan; Atocin; Mylofanol; Rhematan; Rheumin; Tophol; Polyphlogin; Quinofen; Tophosan
Molecular Formula: C16H11NO2
Molecular Weight: 249.26
Percent Composition: C 77.10%, H 4.45%, N 5.62%, O 12.84%
Literature References: Quinoline derivative formerly used in treatment of chronic gout: A. B. Gutman, Arthritis Rheum. 16, 431 (1973). Prepd by heating pyruvic acid with aniline and benzaldehyde or with benzylidene aniline in abs alcohol: Doebner, Gieseke, Ann. 242, 290 (1887). Also from acetophenone and isatinic acid in alcoholic KOH: Pfitzinger, J. Prakt. Chem. 38, 582 (1882); 56, 293 (1897). Cinchophen as ulcerogenic agent: T. P. Churchill, F. H. van Wagoner, Arch. Pathol. 13, 850 (1932); N. Umeda et al., Toxicol. Appl. Pharmacol. 18, 102 (1971); T. H. Stewart et al., J. Pathol. 131, 363 (1980). Mitochondrial toxicity of cinchophen and derivatives: H. Vainio et al., Biochem. Pharmacol. 20, 1589 (1971).
Properties: Needles, mp 213-216°. Stable to air, but turns yellow under the influence of light. Slightly bitter taste. Practically insol in water. One gram dissolves in about 400 ml chloroform, in about 100 ml ether and in about 120 ml alcohol.
Melting point: mp 213-216°
 
Derivative Type: Hydrochloride
CAS Registry Number: 132-58-1
Trademarks: Chloroxyl
Molecular Formula: C16H11NO2.HCl
Molecular Weight: 285.72
Percent Composition: C 67.26%, H 4.23%, N 4.90%, O 11.20%, Cl 12.41%
Properties: Yellow cryst powder, slightly bitter, astringent taste; mp about 223°. Practically insol in water. Slightly sol in alcohol; sol in chloroform, ether.
Melting point: mp about 223°
 
Derivative Type: Allyl ester
CAS Registry Number: 524-34-5
Additional Names: Allyl 2-phenylcinchoninate
Trademarks: Atoquinol
Molecular Formula: C19H15NO2
Molecular Weight: 289.33
Percent Composition: C 78.87%, H 5.23%, N 4.84%, O 11.06%
Literature References: Prepn: Gams, US 1336952 (1920).
Properties: Long needles from alc, mp 30°. bp15 260°. Practically insol in water. Readily sol in alcohol, ether, acetone, oils. Tasteless.
Melting point: mp 30°
Boiling point: bp15 260°
 
Use: Experimentally to induce ulcers.
Therap-Cat: Formerly as analgesic.
Keywords: Analgesic (Non-Narcotic).

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