| Identification | Back Directory | [Name]
pilocarpidine | [CAS]
127-67-3 | [Synonyms]
pilocarpidine
Einecs 204-856-8
N-Demethylpilocarpine
2(3H)-Furanone, 3-ethyldihydro-4-(1H-imidazol-4-ylmethyl)-, (3S,4R)-
(3S,4R)-3-Ethyl-4,5-dihydro-4-[(1H-imidazol-5-yl)methyl]furan-2(3H)-one
(3S,4R)-3-Ethyl-4,5-dihydro-4-[(1H-imidazole-5-yl)methyl]-2(3H)-furanone | [EINECS(EC#)]
204-856-8 | [Molecular Formula]
C10H14N2O2 | [MOL File]
127-67-3.mol | [Molecular Weight]
194.23 |
| Hazard Information | Back Directory | [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]20D + 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]20D + 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)
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