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)
