Akuammicine-obtained from the plant substance of Catharanthus roseus

B. Akuammicine


Biological Source It is obtained from the plant substance of Catharanthus roseus (L.) G. Don (Apocyanaceae) (Periwinkle, Madagascar or Cape Periwinkle, Old Maid); and also from the seeds of Picralima klaineana, Pierre, belonging to the natural order (Apocyanaceae).
Chemical Structure

Akuammicine
2, 16, 19-20-Tetradehydrocuran-17-oic acid methyl ster; (C20H22N2O2).
Characteristic Features
1. It is obtained as plates from a mixture of ethanol and water having mp 182°C.
2. Its physical parameters are: [α]16D – 745° (C = 0.994 in ethanol); pKa 7.45; and uvmax (ethanol): 227, 330 and 330 nm (log ε 4.09, 4.07, 4.24).
Identification Tests It forms the following derivatives:
1. Akuaminicine Hydrochloride Dihydrate (C20H22N2O2.HCl.2H2O): It is obtained as leaflets from ethanol or water having mp 171°C; and has [α]21D – 610° (C = 1.430 in ethanol).
2. Akuaminicine Perchlorate Monohydrate (C20H22N2O2.HClO4.H2O): It is obtained as needles from a mixture of ethanol and water having mp 134-136°C.
3. Akuammicine Hydroiodide Monohydrate (C20H22N2O2.HI,H2O): It is obtained as square plates from water having mp 128°C.
4. Akuammicine Methiodide: It is obtained as crystals from water with mp 252°C.
5. Akuammicine Nitrate: It is obtained as needles from hot water having mp 182.5°C.
Uses The drug exhibits a slight digitalis-like reaction; and is, therefore, believed to act as a heart poison.

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