356 poisons : their effects and detection. [§§ 424, 425- 
Cocaine , C 17 tL 21 N0 4 , is the chief coca alkaloid of importance, and the other alkaloids 
are commercially converted into cocaine by first obtaining ecgonine from them, treat¬ 
ing this with benzoic anhydride, which converts it into benzoyl ecgonine, and then 
esterifying the carboxyl groups with methyl alcohol, which converts it into cocaine. 
Thus— 
C 17 H 21 N0 4 +2H 2 0 -> C 9 H 15 N0 3 -f c 7 h 6 o 2 +ch 3 oh 
Cocaine. Ecgonine. Benzoic ^Methyl 
acid. alcohol. 
2 C 9 H 15 NG 3 +(C 6 H 5 C0) 2 0 ->2C 9 H 14 N0 3 (C0C 6 H 5 ) + H 2 0 
Ecgonine. Benzoic Benzoyl ecgonine. 
anhydride. 
C 16 H 19 N0 4 +CH 3 0H -> c 17 h 21 no 4 +h 2 o 
Benzoyl Methyl Cocaine, 
ecgonine. alcohol. 
Cocaine crystallises from alcohol in prisms melting at 98°. Soluble in 10 parts 90 
per cent, alcohol, 4 of ether, 0-5 of chloroform, and almost insoluble in water. Natural 
cocaine is bitter, alkaline to methyl orange, and lsevorotatory ; the specific rotatory 
power of its hydrochloride in water = —71-95°, and it yields l-ecgonine. From d-e ego- 
nine may be prepared d-cocaine, which melts at 46-47° C., and from inactive ecgonine 
may be prepared inactive cocaine, melting at 80° C. ; this variety is soluble in alcohol 
and ether, and is probably a racemic variety of natural cocaine. 
The constitution of ecgonine and a-eegonine may be represented as follows:— 
CH 2 —CH—CH—CO OH 
N—CH 3 >CHOH 
\ / 
CH, ; -CH—CH 2 
Ecgonine. 
CH 2 —CH—CH 2 
/OH 
N-CH 3 >c< 
/ \COOH 
CH 2 CH CH 2 
a-Ecgonine. 
§ 424. Cocaine Hydrochloride (C 17 H 21 N0 4 HC1).—Crystallised from 
alcohol, cocaine hydrochloride appears in prismatic crystals ; these 
crystals, according to Hesse, 1 when perfectly pure, should melt at 
186°, although the melting-point is generally given as 200° or even 202°. 
Cocaine hydrochloride is soluble in 0-5 part of water, 3 parts of 90 per 
cent, alcohol, and insoluble in olive oil. 
§ 425. Pharmaceutical Preparations. —The official preparations are : — 
1. Cocaine hydrochloride. 
2. Hypodermic injection of cocaine. 5 grms. cocaine hydrochloride 
and 0-15 grm. salicylic acid in 100 c.c. of water. 
3. Krameria andcocaine lozenges (syn. Rhatany and cocaine lozenges). 
Each lozenge contains 3 mgrms. of cocaine hydrochloride, with 60 mgrms. 
of krameria extract. 
4. Cocaine ointment. Made with oleic acid and lard. The ointment 
contains 4 per cent, cocaine. 
5. Cocaine discs. The discs are made for ophthalmic use with 
gelatine and glycerine. Each disc should contain 1-3 mgrm. cocaine 
hydrochloride. 
It will be observed that, of the five preparations, one alone—the 
ointment—contains the base ; in the other four the hydrochloride is the 
1 O. Hesse, Annalen, cclxxvi. 342-344. 
