Jan. 13, 1923 
Poisonous Properties of Bikukulla cucullaria 75 
products were obtained, but from the ether extract a crystalline alkaloid 
was isolated. After the ether was distilled off the residue was triturated 
with dilute hydrochloric acid until all the alkaloid was removed and the 
acid solution was made ammoniacal and shaken out with ether. The 
etherial solution was concentrated to small bulk, the same volume of 
alcohol was added, and on slow evaporation there were deposited warty 
masses of colorless crystals. These were removed and pressed between 
filters and recrystallized from a mixture of alcohol and chloroform. After 
one recrystallization they melted at 168 0 C., which was not changed by a 
further purification of the same kind. It was at once assumed that the 
dicentrine of Asahina (1) had been isolated, but after testing the com¬ 
pound on mice it w^as evident that it was another substance, and one of 
much higher degree of toxicity. By methods already described, it was 
found that 0.04 mgm. of the alkaloid was fatal to a mouse. The animal 
exhibited a period of intense excitement followed by convulsions and 
death, whereas Iwakawa in trying out dicentrine on mice found the fatal 
dose to lie between 5 and 10 mgm., and his animals experienced a pro¬ 
longed period of narcosis before death. These facts would seem sufficient 
to differentiate the two compounds. 
Another alkaloid is known with a melting point of 169° C., namely, 
Y-homochelidonine, found chiefly in Sanguinaria canadensis fi. It has 
always been prepared in conjunction with its physical isomeride B- 
homochelidonine, melting point 159 0 , but no trace of the latter was found 
in our product. Moreover, the physiological action of Y-homochelido¬ 
nine is like morphine, chiefly narcotic. It is therefore reasonable to as¬ 
sume that the alkaloid isolated from Bikukulla cucullaria is new, and we 
propose to name it provisionally cucullarine. Unfortunately, the small 
quantity at our disposal has made it impossible to make a complete 
study of it, but this we intend to do later when larger quantities of 
material are available. We have been able, however, to note the follow¬ 
ing properties: It crystallizes in characteristic warty masses of prisms; 
it is colorless when first prepared but changes to pink in the light; it is 
soluble in ether and chloroform, but not so soluble in alcohol; it is precipi¬ 
tated by the usual alkaloid reagents, Mayer’s, iodin in potassium iodid, 
picric acid (crystalline), and platinum chlorid; with concentrated sul¬ 
phuric acid a small crystal dissolves with difficulty, producing a violet 
coloration turning brown. 
Another portion of Bikukulla cucullaria was exhaustively extracted 
with 95 per cent alcohol containing a little acetic acid, the alcohol was 
removed by vacuum distillation, and the residue was taken up in dilute 
acetic acid and allowed to stand for some time. The small quantity of 
resin which separated was filtered off, and the solution was made alkaline 
with ammonia and shaken out first with ether then with chloroform. 
Very little alkaloid was recovered from the latter extract, the great bulk 
being removed by the ether. The etherial solution was set aside for sev¬ 
eral days with the expectation that protopine would crystallize out. 
This did not occur, however. The ether was then distilled off, and the 
raw alkaloid fractioned in various ways with the production only of 
amorphous products. Our failure to isolate protopine, reported by 
Fischer and Soell in B. cucullaria , may be due to the comparatively 
small quantities of material on which the work was done or to the stage of 
maturity of the plant. Fischer and Soell do not say when their B. 
cucullaria was gathered and are rather obscure in their description of the 
technic they employed. 
