Karl Bödeker, of Göttingen, has opened the road in this direction, and gives in a paper sent to Liebig's Annalen der Chemie, August 15, 1881, the following account of an alkaloid, which, from the name of the plant in which it occurs, he calls lycopodine.
The plant yielding the alkaloid, Lycopodium complanatum, belongs to the group of angiospermous cryptogams. It is distributed throughout the whole of north and middle Europe, and contains the largest proportion of aluminum of any known plant. Its bitter taste led the author to suspect an alkaloid in it.
To prepare the alkaloid the dried plant is chopped up and twice exhausted with boiling alcohol of 90 per cent. The residue is squeezed out while hot, and the extract, after being allowed to settle awhile, is decanted off, and evaporated to a viscid consistency over a water bath. This is then repeatedly kneaded up with fresh quantities of lukewarm water until the washings cease to taste bitter, and to give a reddish brown coloration when treated with a strong aqueous solution of iodine. The several washings are collected and precipitated with basic lead acetate, the precipitate filtered off, and the lead in the filtrate removed by sulphureted hydrogen. The filtrate from the lead sulphide is evaporated down over a water bath, then made strongly alkaline with a solution of caustic soda, and repeatedly shaken up with fresh quantities of ether so long as the washings taste bitter and give a precipitate with iodine water. After distilling off the ether, the residue is treated with strong hydrochloric acid, the neutral or slightly acid solution filtered off from resinous particles, slowly evaporated to crystallization, and the crystals purified by repeated recrystallization. To prepare the pure base a very concentrated solution of this pure hydrochlorate is treated with an excess of a very concentrated solution of caustic soda, and pieces of caustic potash are added, whereupon the free alkaloid separates out at first as a colorless resinous stringy mass, which, however, upon standing, turns crystalline, forming monoclinic crystals similar to tartaric acid or glycocol. The crystals are rapidly washed with water, and dried between soft blotting paper.
Thus prepared, lycopodine has a composition which may be represented by the formula C32H52N2O3. It melts at 114° to 115° C. without loss of weight. It is tolerable soluble in water and in ether, and very soluble indeed in alcohol, chloroform, benzol, or amyl alcohol. Lycopodine has a very pure bitter taste.
The author has formed several salts of the base, all of a crystalline nature, and containing water of crystallization.
The hydrochlorate gives up a part of its water of crystallization at the ordinary temperature under a desiccator over sulphuric acid, and the whole of it upon heating.—Chemist and Druggist.
CONCHINAMINE.
Some years ago, O. Hesse, when preparing chinamine from the renewed bark of Cinchona succirubra, found in the mother liquid a new alkaloid, which he then briefly designated as conchinamine. He has lately given his attention to the separation and preparation of this alkaloid, and gives in Liebig's Annalen der Chemie, August 31, 1881, the following description of it:
Preparation.—The alcoholic mother lye from chinamine is evaporated down and protractedly exhausted with boiling ligroine, whereby conchinamine and a small quantity of certain amorphous bases are dissolved out. Upon cooling the greater part of the amorphous bases precipitates out. The ligroine solution is then first treated with dilute acetic acid, and then with a dilute solution of caustic soda, whereupon a large quantity of a resinous precipitate is formed. This is kneaded up with lukewarm water to remove adherent soda, and then dissolved in hot alcohol. The alcoholic solution is saturated with nitric acid, which has been previously diluted with half its volume of water, and the whole set aside for a few days to crystallize. The crystals of conchinamine nitrate are purified by recrystallization from boiling water. On dissolving these pure crystals of the nitrate in hot alcohol of 60 per cent., and adding ammonia, absolute pure conchinamine separates out on cooling.