1911 Encyclopædia Britannica/Pilocarpine

PILOCARPINE, C₁₁H₁₆N₂O₂, an alkaloid found, together with isopilocarpine and other related compounds, in the leaves of jaborandi (Pilocarpus pennatifolius). It was first isolated by E. Hardy in 1875 (Ber., 8, p. 1594), and is a crystalline, very hygroscopic solid It is a strong poison. It has the properties of a monacid base and contains the methylamino group, ·NCH₃. When heated with hydrochloric acid it gives isopilocarpine Isopilocarpine was isolated in 1900 by H. A. D. Jowett (Journ. Chem. Soc. 77, p. 473), and is a colourless oil which boils at 261° C. (10 mm.). It is a monacid base which is readily soluble in solutions of the caustic alkalis. Jowett is of the opinion that pilocarpine and isopilocarpine are stereo-isomers of the structure:—

N	CH·N·CH3C2H5·CH·CO	O
	| |
	CH : C—CH2—CH·CH2