COCAINE, kffIca-In, a vegetable allcaloid, with the chemical formula CrrfluNO., obtained from the leaves of the coca shrub (Erythroxy Ion coca) growing on the eastern slo.pes of the Andes and cultivated in Peru, Bolivia, Colom bia and Brazil, and in Java, Ceylon and the Malay States. Cocaine was first isolated by Nicmann in 1860. Its anwstlictic qualities were disc-overed by von Anrep in 1880, but it did not come into use as a surgical adjunct until Koller in 1884 began to employ it to produce local anwsthesia in operations upon the eye.
The leaves of the coca contain alkaloids of four types: (1) Cocaines— alkyl acyl deriva tives of ecgonine; (2) acylecgonmes— acyl de rivatives ecgonme; (3) pseudotropeines — acyl derivatives of pseudotropeine; and (4) hygrines. The first and second types may be used as commercial sources of ecgonine, and thus for thc manufacture of crystalline cocaine — benzomethyl ecgonine. The South American leaves yield about 1 per cent of total allcaloids, mostly cocaine; the Ceylon and Malay leaves contain up to 1.6 per cent of total alkaloids, of which about 65 per cent is cocaine; the Java leaves contain 1.6 per cent of alkaloids, scarcely any of which is cocaine, but from which cocaine is readily obtained.
In Peru the coca leaves are macerated in water containing dilute sulphuric acid in a series of four vessels, in each of which the leaves remain four days, the liquor being changed every day from the oldest tank to the next newer, the leaves from the oldest being thrown away. To this concentrated liquor is added carbonate of soda in a 60° (Be) solution. This precipitates the cocaine in solid form. Petroleum is then introduced and the whole gently agitated. The petroleum takes up the cocaine and is then washed with water to remove "the last trace of acid. It is then treated with water containing dilute sulphuric acid in which the cocaine is redissolved, the whole being violently agitated for 30 to 40 minutes. After standing a short time the cocaine solution is drawn off, leaving the oil to be used again. The acid solution is treated
with sodium carbonate and allowed to stand 12 hours, and then passed through a filter which collects the precipitate. This is washed with distilled water and pressed into a brown paste in a filter press. Another method prac tised with the imported dry coca leaves is to macerate them, adding the sodium carbonate solution and the petroleum and agitating the mixture for some hours. The cocaine with cinnamyl cocaine cetc.) are taken tip by the petroleum, which is then shaken with dilute hydrochloric acid. The resulting hydrochloride of cocaine crystallizes out and is pressed and dried. This crude salt is purified by dissolving in water, liberating the free base by ammonia and redissolving in alcoholic hydrogen chloride. The pure cocaine hydrochloride crystallizes out. The mother liquor contains the other coca al kaloids, and these are converted into cocaine by heating with boiling hydrochloric acid and pouring into water. The truxillic acids sep arate and are filtered off. The filtrate is con centrated until ecgonine hydrochloride crystal lizes out. This is benzoylated and methylated in turn to produce cocaine.
The crude cocaine of commerce is con verted into hydrochloride, in which form it is used as a drug, by first dissolving it in dilute hydrochlonc acid and then treating cold with a •solution of potassium permanganate — which destroys the larger part of the alkaloids accom panying the cocaine before attacking the latter. At that point the action is checked by adding sodium carbonate, and the precipitate is taken up with ether. The ether solution is evaporated to dryness and the residue dissolved in acetone and treated with hydrochloric acid.
Cocaine crystallizes from its alcoholic solu tion in small monoclinic prisms which melt at 208° F. and dissolve sparingly in cold water — though fairly in hot water — and freely in ether and alcohol. The hydrochloride is readily soluble in water.