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LYCOPODINE.

While the phanerogams or flowering plants annually contribute to the list of newly discovered alkaloids, with the exception of muscarine and amanitine, no alkaloid has as yet been definitely recognized among the cryptogams.

Karl Boedeker, of Goettingen, 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 C_{32}H_{52}N_{2}O_{3}.  It melts at 114 deg. to 115 deg.  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.