Psilocaulon absimile N.E.Br. as a stock poison : II. Isolation of the toxic alkaloidal constituent and its identification as piperidine hydrochloride

Abstract

The alkaloid present in Psilocaulon articulatum, N.E.Br. has been isolated and identified as Piperidine. It occurs in plant in part as the hydrochloride and is present to the extent of approximately 4.5 per cent. Of the dry weight. Piperidine picrolonate has been prepared and described. It crystallises in golden-yellow hexagonal tables with M.P. 232-234°. The melting point of piperidine picrate is recorded as 149-149.5° and that of the gold salt as 173-176°. Piperidine has not hitherto been found as a naturally occurring alkaloid in plants, although it is component of certain important alkaloids such as, for example, piperine and coniine. Only one other alkaloid has been reported in the family Aizoaceae, the alkaloid “Mesembrine” which was not definitely characterised as a pure substance. Death due to acute poisoning following the ingestion of Psilocaulon absimile by grazing stock is to be attributed in large measure to the action of the alkaloid. Chronic poisoning is almost certainly due to the effects of the large quantity of oxalic acid which the plant also contains. The toxicological effects upon rabbits and frogs of preparations of piperidine hydrochloride obtained from the plant are briefly described in the present paper. Good quality piperidine is only obtainable commercially at a high price, about £6.8s. per lb., and it is suggested that the plant Psilocaulon absimile, which is widely distributed in the Union and useless as a fodder, might serve as cheap alternative source for the manufacture of this material.