The action of the cinchona and certain other alkaloids in bird malaria. Pt. 2 / by G.A.H. Buttle, T.A. Henry and J.W. Trevan.

  • Buttle, G. A. H. (Gladwin Albert Hurst), 1899-1983.
Date:
[1934]
Catalogue details

Licence: Public Domain Mark

Credit: The action of the cinchona and certain other alkaloids in bird malaria. Pt. 2 / by G.A.H. Buttle, T.A. Henry and J.W. Trevan. Source: Wellcome Collection.

    14/22 (page 438)
    or cone. HC1 (1 g. in 8 ml.), m.p. 263° (decomp.). (Found: C, 45-5; H, 5-08; N, 5-76; Cl, 28-04; Zn, 12-7 %. Calc.: C, 45-2; H, 4-80; N, 5-56; Cl, 28-1; Zn, 12-9 %.) Two cinchonine zincichlorides have been described already [Grazinghoff, 1865] to which the following formulae were assigned (C19H22ON2.2HCl)2, ZnCl2, 2H20 and (C19H22ON2.3HCl)2, ZnCl2, H20. It is suggested that these products were probably mixtures in which each of the two zincichlorides referred to above was still contaminated with cinchonine hydrochloride, which in the present instance separated as a first fraction in recrystallising the crude product. The base recovered from the normal zincichloride made from crude cinchonine showed hydrogen absorption 84-0 % as against 86-2 % for the starting material, so that this derivative is of no value for purification purposes. Cinchonine cuprichloride. The possibility of using the cuprichloride as a means of purifying cinchonine was investigated as described under quinidine (p. 435). After numerous trials, the best results were obtained by using equal quantities of cinchonine and cupric chloride dissolved separately to produce a final solution of solids (1 g.) in cone. HC1 (8 ml.), recrystallising the resulting cuprichloride from hot cone. HC1 (1 g. in 3 ml.), and recovering the base in the usual way from the recrystallised cuprichloride. Cinchonine dihydrochloride is very soluble in writer so that no further fractionation can be effected by solution of the cuprichloride in a small quantity of water as in the case of quinidine (p. 435). The following are typical results: Hydrogen absorption, % Initial cinchonine 71-5 85-2 96-4 96 to 97 Recovered cinchonine 89-6 96-4 99-0 100-1 Yield, % 78-0 88-0 61-0 59-4 That is, starting with quinidine-free “cinchonine” showing hydrogen absorption of about 85 %, two passages through the cuprichloride are necessary to raise the hydrogen absorption to 99— 100%. The cinchonine used for the final determination of the constants recorded in Table IV was prepared partly by fractionation of the dihyclrobromide and partly by the cuprichloride method, and no difference could be detected between the two products. Table IV. Constants of pure cinchona alkaloids. Methoxyl-free bases: cinchonidine, dihydrocinchonidine; cinchonine, dihydrocinchonine. Substance Cinchonidine (Cd): Base, m.p. 204-5° Acid sulphate, Cd. H2S04, 5H20 55 55 Dihydrobromide, Cd’.2HBr, 2H20 Dihydrocinchonidine (HCd): Base, m.p. 232° Acid sulphate, HCd. H2S04, 5H20 Dihydrobromide, HCd.2HBr, 2H20 5 5 55 Cinchonine (Cn): Base, m.p. 254° Dihydrobromide, Cn.2HBr Dihydrocinchonine (HCn): Base, m.p. 267° Dihydrobromide, HCn.2HBr 55 ?? <xD c* Solvent - 2-617° ilf/40 A/10 H2SO -10-498 ilf/10 Water - 2-613 ilf/40 55 - 2-615 ilf/40 A/10 H2SO. -10-112 ilf/10 Water - 2-607 ilf/40 55 - 2-604 ilf/40 A/10 H2SO, - 2-140 ilf/40 A/10 H2S<+ - 8-417 M/10 Water - 2-132 ilf/40 A/10 H2SO, - 8-149 ilf/10 Water - 2-128 ilf/40 55 + 3-876 ilf/40 A/10 H2S04 + 15-238 ilf/10 W ater + 3-867 ilf/40 55 + 3-342 ilf/40 A/10 H2S04 +13-154 ilf/10 Water + 3-347 ilf/40 55 wy calc, for c A Additional Salt Base constants -178° H.A.t =101-2 — 133-9C 1 -178-5 H.A. =100-2: pH=2 -133-6 -178-1 pH=3-05 -133-4 -177-8 — -110-9 -172-0 pH =2-52 -114-3 -177-3 pH=2-89 -114-2 -177-2 ■- _ -144-6 — -106-8 -142-2 — -108-3 -144-1 — - 89-0 -137-7 — - 92-9 -143-7 — +263-7 H.A. =100-1 % +167 +259-2 H.A. =99-74 % + 169-6 +263-1 — . +225-8 — + 143-6 +222-2 — + 146-2 +226-1 —- * c is expressed on dry substance. t H.A. = hydrogen absorption: % of calculated value (p. 432).