Frankforter : the alkaloids of veratrum. 1043 



Veratrine allyliodide C32 H^ NO<>- C 3 H& I. By digesting vera- 

 trine with allyliodide on a water bath for several hours, a solid 

 but slightly waxy looking substance was formed. The excess 

 of allyliodide was removed and the veratrine compound washed 

 thoroughly with ether. The substance thus purified appeared 

 partially crystalline but changed on standing in the air to a 

 semi-waxy mass. Exposed for some time to the air or by 

 treating with a small quantity of water and stirring, the sub- 

 si a nee again becomes granular. The substance was finally 

 purified by dissolving in a small quantity of alcohol and pre- 

 cipitating with ether. The pure iodide is an almost white 

 crystalline powder. It is soluble in ethyl and methyl alcohols 

 and acetone. It melts at 235°-236°. It contains one molecule 

 of water which can be removed by drying at 100°. 



I. .1990 grms of the dried sub. gave 0.4000 COo and .1202 H.> O 

 II. .3022 " " " " " 0.0954 Ag I. 



Calculated for Found 



C32 H 49 N0 9 • Cj H 5 1 I II 



C=55.29 54.81 



H= 7.1 6.71 



1=16.73 17.01 



An attempt to obtain the free base by shaking with silver 

 oxide was unsuccessful. The solution turned brown at the 

 ordinary temperature giving off the order of allylalcohol. 



The structural formula for veratrine is still a mystery. From 

 the odor of picoline by a destructive distillation and isolation 

 of B picoline by Ahrens 35 it is evident that veratrine is a pyri- 

 dine derivative, resembling in many respects nicotine. Whether 

 both cevadic and tig-lie acids are present remains for future 

 experiments to determine. The work of Schmidt and Koppen 

 indicates the presence of both acids while the careful researches 

 of Wright and Luff would indicate that these isomeric acids 

 were converted into each other by special reagents. Assuming 

 that but one acid is present the following formula may be as- 

 signed to veratrine: 



I O CH 3 



I o H 



c 21 h 3j o, -; OOCCH (CH;j ) CH;i 

 In h 7 c g 



Experiments are being conducted at present along this line 

 with the hope of throwing more light on the structure of this 

 important compound. 



(25) Her. 23:2700. 



