Title: Quinacrine
CAS Registry Number: 83-89-6
CAS Name: N4-(6-Chloro-2-methoxy-9-acridinyl)-N1,N1-diethyl-1,4-pentanediamine
Additional Names: 6-chloro-9-[[4-(diethylamino)-1-methylbutyl]amino]-2-methoxyacridine; 3-chloro-7-methoxy-9-(1-methyl-4-diethyl aminobutylamino)acridine; 2-chloro-5-(w-diethylamino-a-methylbutylamino)-7-methoxyacridine; mepacrine
Molecular Formula: C23H30ClN3O
Molecular Weight: 399.96
Percent Composition: C 69.07%, H 7.56%, Cl 8.86%, N 10.51%, O 4.00%
Literature References: Prepd by condensing 1-diethylamino-4-aminopentane with 3,9-dichloro-7-methoxyacridine: F. Mietzsch, H. Mauss, DE 553072; DE 571499 (1934); eidem, US 2113357 (1938 to Winthrop Chemical); cf. Drosdov, Cherutzov, J. Gen. Chem. USSR 5, 1576, 1736 (1935); 8, 1192 (1938); Magidson, Grigorovskii, Khim. Farm. Prom. 1933, 187; Jensch, Eisleb, US 1782727 (1930); Schulemann et al., US 1889704 (1932). Review of quinacrine and other acridines: A. O. Wolfe in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 203-233.
Derivative Type: Dihydrochloride dihydrate
CAS Registry Number: 6151-30-0
Manufacturers' Codes: RP-866; SN-390
Trademarks: Atabrine hydrochloride (Sanofi Winthrop)
Molecular Formula: C23H30ClN3O.2HCl.2H2O
Molecular Weight: 508.91
Percent Composition: C 54.28%, H 7.13%, Cl 20.90%, N 8.26%, O 9.43%
Properties: Bitter, bright yellow crystals. Dec 248-250° (mp poorly discernible). One gram dissolves in ~35 ml water. Much more sol in hot water. Slightly sol in ethanol, somewhat more sol in methanol. Insol in ether, benzene, acetone. pH of a 1% aq soln ~4.5. Under uv light the yellow aq solns exhibit a vivid fluorescence which is detectable in a dilution of 1:5,000,000.
Derivative Type: Methanesulfonate monohydrate
CAS Registry Number: 6598-46-5
Molecular Formula: C25H38ClN3O7S2.H2O
Molecular Weight: 610.18
Percent Composition: C 49.21%, H 6.61%, Cl 5.81%, N 6.89%, O 20.98%, S 10.51%
Properties: Bitter, bright yellow crystals. One part dissolves in 3 parts water at 15.5°, in 36 parts 95% alcohol at 15.5°. pH of 2.0% w/v soln in water 3.0-5.0.
Therap-Cat: Anthelmintic (Cestodes); antimalarial.
Therap-Cat-Vet: Antiprotozoal, teniacide.
Keywords: Anthelmintic (Cestodes); Antimalarial. |