336 TIIK ACTIVE PRINCIPLE OF ERYTIIROPULOEUM LABOrCHERII, 



Power and Salway (19) iu 1912, from bark collected iii tlie Hclgiau CougO) 

 isolated an alkaloid which iigrced in its properties and composition with that of 

 Harnack. These two authors worked also on a commercial specimen obtained 

 from Merck. Merck prepared the hydrochloride salt with dry gas: the salt was 

 obtained in the form of a viscid oil and not as before in the amorphous solid 

 state (18). This hydrochloride gave the formula ('-sllisOTN.HCl with ((.9 

 % CI (19). 



The free alkaloid erythrophleine was obtained by i)recipitating the aqueous 

 solutions of its salts by alkalies. The lirst flocculent precipitate soon collected 

 into a resinous mass, and finally changed to a thick yellow syrup. It was very 

 soluble in alcohol, ether, ethyl acetate and dilute acids, Ijut insoluble in petroleum 

 spirit or benzene. The substance was very easily decomposed, evaporation in 

 a solution which was not quite neutral being sulTicient to change it partly. When 

 heated with acids or alkalies, the solution became yellow, then a brown resinous 

 substance separated, which cooled to a hard brittle solid. This was erythrophleie 

 acid, C'27 H40 08. It was nitrogen-iree, and nearly insoluble in water and acids. 

 It was soluble in alcohol, ether and alkalies. When erythrophleine was heated 

 in this way for a short time only, the nitrogen-free acid which was obtained re- 

 duced Fehling's solution, but when the heating was continued to complete des- 

 truction of the alkaloid there was no reduction. The reducing was, therefore, 

 due to some intermediate product, which was gradually destroyed. This decom- 

 position was also accompanied by the evolution of a volatile base, which, in the 

 case of material from certain sources, was a nicotine-like base called mauconine, 

 and with that obtained from other sources was shown to be methylamine. 



Experimental. 



The problem presented is to detemiine by practical experim<'nt whether the 

 Australian tree, ErythrophJoeum Laboucherii, owes its poisonous properties to 

 the presence in it of some definite chemical compound like the alkaloid of E. 

 gidneense, and whether such an alkaloid, if present, is identical with tlic erythro- 

 phleine isolated from that plant. 



The material for this investigation was kindly offered by Mr. J. H. Maiden, 

 Director of the Sydney Botanic Gardens. The plant was collected at the be- 

 ginning of 1920 by Mr. Allen, Curator of the Botanic Gardens of Dai-win, in 

 the Northern Territory. To both, the writer takes this opportunity of express- 

 ing his indebtedness and thanks. 



The sample consisted of a small anuniiit of air-<lried leaves and a few 

 beans. 



Preliminarji Tests. — An extract was prepared by macerating a small amount 

 of the leaves, and also of the beans, in alcohol. When the solvent was distilled 

 and the solid extract treated with slightly acidulated water, a solution was ob- 

 tained which gave very strong indication of the presence of an alkaloid in con- 

 siderable amount. 



The alkaloid was contained in the leaves and, in relatively greater quantity, 

 in the beans. 



The characteristic tests for other active plant-principles gave negative re- 

 sults: cyanogenetic glucosides and saponins were proved to be absent. 



The amounts of ash and water contained in the leaves and beans were 

 estimated. 



Leaves. Beans. 



The air-dried powder contained water 8.73 % 10.1 % 



ash 2.45 2.5 



f 



