pilocarpidine Property

Boiling point:

457.0±18.0 °C(Predicted)

Density 

1.186±0.06 g/cm3(Predicted)

pka

14.30±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

pilocarpidine Chemical Properties,Usage,Production

Description

The leaves of Pilocarpus Jaborandi contain this alkaloid but not those of P. microphyllus. The alkaloid is a viscous oil which decomposes on attempted distillation. It has [α]²⁰_D + 81.3° (H20) falling to + 35.2° on the addition of alkali. The salts are well crystallized and include the hydrochloride which has [α]~O + 72° (H20); nitrate, m.p. 137°C; [α]²⁰_D + 73.2° (H20); aurichloride, m.p. 125 C and the platinichloride tetrahydrate, m.p. 187°C (dry, dec.). In contrast to the corresponding salts of pilocarpine and isopilocarpine (q.v.) the picrate is a non-crystallizable oil. When heated with alkalies, the salts evolve dimethylamine and on treatment with alcoholic sodium methoxide, the base gives isopilocarpidine, characterized as the nitrate, m.p. 109-111 °C. The latter, on quaternary methylation furnishes isopilocarpine metho-salts, e.g. the methopicrate, m.p. 119-120°C.

Definition

ChEBI: Pilocarpidine is a gamma-lactone.

References

Harnack., Annalen, 238,230 (1887)
Jowett., J. Chem. Soc., 77,474 (1900)
Burtles, Pyman, Roylance., ibid, 127,581 (1925)
Spath, Kunz., Ber., 58,513 (1925)
Preobrashenski et al., ibid, 69, 1837 (1936)