PILOCARPINE. 
423 
§§ 508-510.] 
sensitive to physostigmine than dogs or cats ; and 3 mgrms. per kilo— 
that is, about 205 mgrms. (3 grains)—would be much beyond the least 
fatal dose. 
IX. - Pilocarpine. 
§ 508. From the leaves of the jaborandi there have been separated 
pilocarpine and its stereo-isomeride isopilocarpine, pilocarpidine, and pilo- 
sine ; the latter, on boiling several hours with 20 per cent, alkali, splits up 
into benzaldehyde and a new base, pilosinine. The relationship of these 
bases one to another is as follows :— 
ch 2 - 
-CH—CH 2 - 
—CNMe 
II 
00 
\ 
ch 2 
/ 
II 
CH—N 
CoFL—CH—CH—CH 9 —C.NMe 
CH 
CO CH, 
CH—N 
\CH 
0 
Pilosinine. 
0 
Pilocarpine. 
C 6 H 5 —CH(OH)—CH—CH—CH 2 —C—NMe v 
CO CH, 
CH—N 
CH 
0 
Pilosine. 
In other words, if a hydrogen in a position in pilosinine is displaced by 
C 2 H 5 , the result is pilocarpine, if by C 6 H 5 CH(OH) the result is pilosine. 
§ 509. Pilocarpine, C 11 H 16 N 2 0 2 , 1 is a soft gelatinous mass, but it 
forms with the mineral acids crystallisable salts. The solutions are 
dextro-rotatory, a D = +100*5°. 
Pharmaceutical Preparations. —Pilocarpine nitrate, C n H 16 N 2 0 2 HN0 3 , 
is official and isthus described in the B.P.:—“A white crystalline powder. 
Soluble in 8 parts of water. Melting-point about 176°. Yields with 
sulphuric acid a colourless solution, slowly becoming green on the 
addition of potassium bichromate. When a solution of 0*01 gramme 
in 5 millilitres of water is mixed with 2 drops of diluted sulphuric acid 
and then with 1 millilitre of solution of hydrogen peroxide, 1 millilitre 
of benzene, and 1 drop of solution of potassium chromate, and the mixture 
well shaken and allowed to separate, the benzene is coloured bluish 
violet. No appreciable ash.” 
§ 510. Tests. —Pilocarpine, either solid or in solution, treated with a 
crystal of potassium bichromate and 1 or 2 c.c. of chloroform, and then 
shaken for a few minutes with 1 c.c. of hydrogen peroxide, imparts 
1 “ Pilocarpine and the Alkaloids of Jaborandi Leaves,” H. A. D. Jowett, Journ. 
Chem. Soc.y T., 1900. 
