CUBEBiE. 587 



Chemical Composition — The most obvious constituent of eubebs 

 is the vohitile oil, the proportion of which yielded by the drug varies 

 from 4 to 13 per cent. The causes of this great variation may be found 

 in the constitution of the drug itself, as well as in the alterabihty of the 

 oil, and the fact that its prevailing constituents begin not to boil 

 below 264^ C. It is, as shown in 1875 by Oglialoro, a mixture of an oil 

 C'"H^*, boiling at 158°-1G3', which is present to a very small amount, 

 and two oils of the formula C''K'\ boiling at 202^-265' C. One of the 

 latter deviates the place of polarization strongly to the left, and yields 

 the crj^stallized compound C^'H-' 2 HCl, melting at 118° C. The other 

 hydrocarbon is less Isevogyrate and cannot be combined with HCl. 



One part of oil of eubebs, diluted with about 20 pai'ts of bisulphide 

 of carbon, assumes at first a greenish, and afterwards a blue coloration, 

 if one drop of a mixture of concentrated sulphuric and nitric acids 

 (equal weight of each acid) is shaken with the solution. 



The oil distilled from old eubebs on cooling at length deposits large, 

 transparent, inodorous octohedra of camphor of cuhehs, C*'H^ + 2 OH^ 

 belonging to the rhombic system. They melt at 65° and may be 

 sublimed at 148°. We have not succeeded in obtaining them by keeping 

 the oil of fresh eubebs for two years in contact with water, to which a 

 little alcohol and nitric acid was added. 



Another constituent of eubebs is Cuhebiii, crystals of which may 

 sometimes be seen in the pericarp even with a common lens. It was 

 discovered by Soubeiran and Capitaine in 1839 ; it is an inodorous 

 substance, crystallizing in small needles or scales, melting at 125°, 

 having a bitter taste in alcoholic solution ; it dissolves freely in boiling 

 alcohol, but is mostly deposited upon cooling ; it requires 30 parts of cold 

 ether for solution, and is also abundantly soluble in chloroform. We 

 found this solution to be slightly Isevogyre; it turns red on addition of 

 concentrated sulphuric acid. If the solution of cubebin in chloroform is 

 shaken with dry pentoxide of phosphorus, it turns blue and gradually 

 becomes red by the influence of moisture. Cubebin is nearly insoluble in 

 cold, but slightly soluble in hot water. Bernatzik (1866) obtained from 

 eubebs 0*40 per cent, of cubebin, Schmidt (1870) 2'5 per cent. The 

 crystals, which are deposited in an alcoholic or ethereal extract of 

 eubebs, consist of cubebin in an impure state. Cubebin is devoid of 

 any remarkable therapeutic action. Its composition, according to 

 Weidel (1877) answers to the formula C'^ff^O"; by melting it with 

 caustic potash, cubebin is resolved as follows : — 



(J'WO' .50 = CO^ . C'H'O^^ . C'ff(OH)-COOH. 



Acetic Acid. Protocatechuic Acid. 



The resin extracted from eubebs consists of an indifferent portion, 

 nearly 3 per cent., and of Cubebic Acid, amounting to about 1 per cent, 

 of the drug. Both are amorphous, and so, according to Schmidt, are the 

 salts of cubebic acid. Bernatzic however, found some of them, as that 

 of barium, to be crystallizable. Schulze (1873) prepared cubebic acid 

 from the crystallized sodium-salt, but was unable to get it other than 

 amoi-phous. The resins, the indifl^erent as well as the acid, possess the 

 therapeutic properties of the drug. 



Schmidt further pointed out the presence in eubebs, of gum (8 per 

 cent.), fatty oil, and malates of magnesium and calcium. 



