1038 MINNESOTA BOTANICAL STUDIES. 



An analysis gave the following: 

 0.1763 grms of the dried sub. gave C.0583 Ag I. 

 Calculated for Found 



C 32 H 49 N0 9 I. 



1-17.68 17.87 



On digesting with strong ammonia for a short time the iodide 

 was completely removed, and a white insoluble gelatinous sub- 

 stance was formed which at first was regarded as the free alka- 

 loid. An examination showed that it differed from veratrine 

 in general appearance and solubility. It melted at 189°. 



Other Compounds. 



Chloralhydroveratrine C Cl 3 GH ~ }J 2 r/ 8 AT/0 S < As stated by 



u {L30 114S lyu s) 



Wright and Luff 24 veratrine heated at 100° with twice its weight 



of benzoic anhydride, is converted into a monobenzoylveratrine 



C32 H 48 (C 7 H 5 O) N0 9 • 

 The formation of this compound proved the presence of one 

 hydroxyl group. The writer repeated the experiment in order 

 to determine whether or not more than one hydroxyl group ex- 

 isted in the alkaloid. The impossibility of making more than the 

 mono derivative was sufficient evidence that but one group ex- 

 isted. It was found, however, that this group was so loosely 

 held that it could be replaced by treating with almost any anhy- 

 dride. Chloral was found to react vigorously on the alkaloid, 

 producing a sort of effervescence. With excess of chloral the al- 

 kaloid dissolves. With a smaller quantity a waxy mass is formed 

 which readily changes to a creamy white granular powder. 

 This powder was washed thoroughly with ether to remove the 

 free chloral. The substance in the pure state was almost white 

 and crystalline. A determination showed the reaction to be 

 quantitative. Five grams of the veratrine gave 6.1 grams of the 

 pure chloral compound. It is insoluble in ether and chloro- 

 form, but very soluble in water and alcohol. It melts at 220°. 

 In its physiological properties it resembles veratrine. It is a 

 most powerful sternutatory, producing the most violent irrita- 

 tion of the nasal mucous membrane. In the most minute quan- 

 tities it effects the eyes, causing intense pain and contracting 

 the pupil. It is a remarkable local irritant. Applied to the 

 moistened skin and rubbed it produces blisters. It is readily 

 decomposed by alkalies. Ammonia decomposes it forming 

 chloral hydrate and veratrine. It is hygroscopic, taking on two 



(34) Journ.Chem. Soc. 32: 351. 



