The action of diazomethane on some picrotoxin derivatives

Abstract

Picrotoxinin C15H16O6, a nitrogen-free, physiologically active body, together with the physiologically inactive Picrotin C15H18O7 form a "molecular" compound Picrotoxin which is easily decomposed into its constituents. Picrotoxin, which was first isolated by Boullay in 1812 from the fruit of the Anamirta Cocculus, has for many years been used as a fish poison and in the treatment of barbituric poisoning. The early workers concerned themselves with the production of the pure material and the establishing of empirical formulae. It was not until after 1863 that the actual chemistry of picrotoxin was more vigorously studied. The investigators fall mainly into five groups:- Barth 1863-84 Paterno 1877-91 Angelico 1907-23 Horrmann 1910-35 Robertson 1935-39. Besides their papers there are a large number of separate publications but although Picrotoxin and both its constituents have been so intensively investigated it is only this year, 1951, that any reasonably satisfactory formulation of the structure of picrotoxinin has been put forward.