The resolution of hyoscine and its components, tropic acid and oscine / by Harold King.

  • King, Harold
Date:
1919]
Catalogue details

Licence: Public Domain Mark

Credit: The resolution of hyoscine and its components, tropic acid and oscine / by Harold King. Source: Wellcome Collection.

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    practically the whole of the meteloidine, was found to be the same as the previously described salt: c= 1*969; l = 2-dcm.; a+l°51'; [a]D+47-0°; [M]D +266-3°. It melted at 224—225°, and a mixture of the two salts showed no depression of the melting point. Isolation of d-Id y oscine Broniocamphorsulphonate.—On continu¬ ing the fractionation, the original mother liquors gave a second crop of crystals, 24'5 grams, [a]D + 44*5°, which, after ten re- crystallisations, gave 11 ‘6 grams of pure r7-hyoscine bromocamphor- sulphonate melting at 159—160° and having [a]D+60*l°. This was twice more recrystallised, and gave 8‘3 grams with [a]D +60-3°. d-llyoscine d-a-bromo-7r-camphorsulphonate crystallises from a mixture of absolute alcohol and excess of dry ethyl acetate in clusters of glistening, acicular needles. After being dried at 110° it melts at 158 160° (161 *5-—163‘5° corr.). Its specific rotation was determined in water at 16°. c = 2‘005 ; Z = 2-dcm.; a+2°25/; [a]D+60-3°; [M]D+370-5°. From this it is calculated that the molecular rotatory power of the r/-hyoscinium ion is 91*8 and the specific rotatory power [aJD is + 30 2 (see r/-hyoscine hydrobromide). The salt is not deli¬ quescent : 0 2730 lost 0-0022 at 100°. Loss = 0-8. 0-1238, dried at 100°, gave 0-2394 C02 and 0-0675 H20. C = 52-8; H = 6'1. Ci7H2iO4N,C10H15O4BrS requires C = 52*7; H = 5-9 per cent. 1 he fractionation of the various liquors was continued, when further small quantities, 4*5 grams in all, of meteloidine bromo- camphorsulphonate, and an additional 12’5* grams of pure ^-hyoscine bromocamphorsulphonate, [a]D+60-5°, were obtained, the original mother liquors now gave 10 grams of a deliquescent salt, [a]D +30-8°, and 2-7 grams, [a]D +273°, both of which had the properties of a slightly impure Z-hyoscine bromocamphor¬ sulphonate, which requires a calculated value of [o]D +29°. On recrystallisation, these gave salts of higher specific rotation. It was not found possible to isolate pure Z-hyoscine bromocamphor¬ sulphonate from the mother liquors. d-Hyoscine Hydrobromide.—Six grams of pure d-hyoscine bromo¬ camphorsulphonate were converted into base, using chloroform and sodium hydrogen carbonate for the regeneration. The base was neutralised with hydrobromic acid and the solution concentrated under diminished pressure. c?-Hyoscine hydrobromide separated on keeping in large tablets (2x1 cm.).