7771. Proflavine

Nomenclature

CAS number: 92-62-6
3,6-Acridinediamine; 3,6-diaminoacridine; 2,8-diaminoacridine.
C13H11N3; mol wt 209.25.
C 74.62%, H 5.30%, N 20.08%.

Description and references

Prepn: M. Sch"opff, Ber. 27, 2320 (1894); DE 230412 (1910 to Cassella), C.A. 5, 2734 (1911); W. P. Thompson, GB 137214 (1919 to Poulenc Frères), C.A. 14, 1445 (1920); A. Albert, J. Chem. Soc. 1941, 121, 484; 1947, 244. Toxicity study: S. D. Rubbo, Br. J. Exp. Pathol. 28, 1 (1947). Review: The Acridines, A. Albert, Ed. (St. Martin's Press, New York, 2nd ed., 1966) pp 300-302; Acridines, R. M. Acheson, Ed. (Interscience, New York, 1956) pp 341-344.

Chemical structure

Properties

Yellow needles from alc, mp 281° (Sch"opff), mp 288° (Albert). Sol in water, ethanol. Practically insol in benzene, ether. pKa 9.7. Solns are brownish and when diluted are fluorescent. Solns should be discarded when they become turbid. LD50 s.c. in mice: 0.14 g/kg (Rubbo).

Derivative

Dihydrochloride.

Nomenclature

CAS number: 531-73-7
C13H11N3.2HCl; mol wt 282.17.
C 55.34%, H 4.64%, N 14.89%, Cl 25.13%.

Properties

Orange-yellow needles. pH of 0.1% soln 2.5-3.0.

Derivative

Sulfate.

Nomenclature

CAS number: 553-30-0
Proflavine hemisulfate; neutral proflavine sulfate.
C13H11N3.H2SO4; mol wt 307.33.
C 50.81%, H 4.26%, N 13.67%, S 10.43%, O 20.82%.

Properties

Occurs as the hydrate. Red needles, hygroscopic. Sol in 300 parts cold water, in 1 part boiling water; slightly sol in alc. Practically insol in ether, CHCl3. pH of satd soln is 6-8. pH of 0.1% soln is 2.5.

Derivative

Mixture with 3,6-diamino-10-methylacridinium chloride see Acriflavine.

Therapeutic Category

Topical antiseptic.

Therapeutic Category (Veterinary)

Topical antiseptic.