SOLANOCAPSINE

Description

A hex acyclic steroidal alkaloid first obtained from the berries of Solanum pseudo_x0002_capsicum L., and later from other Solanum species. The base crystallizes from 50% EtOH in flat prisms and has [α]_D + 25.5° or + 24° (MeOH). The dihydrochloride monohydrate forms needles, m.p. > 280°C; the sulphate, flat colourless prisms, m.p. 324°C; the oxalate, m.p. 288-9°C; picrate, m.p. 194°C; diacetyl derivative, an amorphous powder, m.p. 193-6°C and the trimethyl compound, m.p. 209°C. The nitro so derivative has been prepared with m.p. 194°C. In contrast to most of the Solanum alkaloids, this base does not give a sparingly soluble digitonide.
Watt and his colleagues have stated that the alkaloid induces marked local irritation when injected intravenously. The systematic action is entirely intracardiac, the effects being mainly on the sinus. Large doses disturb conduction and disorganize the action of the heart.

References

Breyer-Brandwyk., Bull. Sci. Pharmacol., 36,541 (1929)
Barger, Fraenkel-Conrat., 1. Chem. Soc., 1537 (1936)
Rochelmeyer, Stiitzel., Arch. Pharm., 282,92 (1944)
Schlittler, Uehlinger., Helv. Chim. Acta, 35,2034 (1952)
Schreiber, Ripperger., Z. Naturforsch., 17b, 217 (1962)
Schreiber, Ripperger., Annalen, 655, 114 (1962)
Budzikiewicz., Tetrahedron, 20,2267 (1964)
Nagai, Sato., Tetrahedron Lett., 2911 (1970)

Raw materials

Preparation Products