ON THE CHEMISTRY OF SOME OF THE LESSER-KNOWN ALKALOIDS. 107 



OTT 



Cevadine, (C 27 H 4l N0 6 ) _ .CO.C(CH 3 )=C 2 H 4 



= CavH^NO^) _ .C 5 H 7 

 Benzoyl Cevadine, (C 27 H 41 N0 6 ) q ' qX C(CR )=C H 



=(c 27 H 41 No 6 )zg;^; 



Cevine, (C 27 H 41 ]SrO c ) _ qjj' 



Veratrine, (C 28 H 44 N0 7 ) . O . CO . C 6 H 3 (0 . CH 3 ) 2 . 

 Verine, (C 28 H 44 N0 7 ) .OH. 



A large proportion of the alkaloidal mixture obtained from V. Saba- 

 dilla seeds, even with most careful working, so as to avoid as much as 

 possible alteration of alkaloids during extraction, refuses to crystallise 

 either as free base or as a salt. This has been considered by Weigelin and 

 by Schmidt and Koppen to indicate the existence of an isomeric amor- 

 phous modification of Cevadine (the Veratrine of Merck) ; another modi- 

 fication being also considered to exist, soluble in water, and obtainable 

 from this amorphous mixture by treatment with water. We find, however, 

 that the amorphous mass is simply a mixture of Cevadine and Veratrine, 

 the one base preventing the other from crystallising in the free state, and 

 the other preventing the sulphate, or other salt of the first, from crystal- 

 lising readily, and the crystallisability being further hindered by the 

 presence of more or less Cevine, Verine, &c, formed by partial spontaneous 

 saponification. This latter, too, is the cause of the partial solubility of 

 the amorphous mixture in water, the cevadates and veratrates formed by 

 the partial change being readily soluble in water. 



Doubtless the " Sabatrine " of "Weigelin was a mixture of saponification 

 and alteration products. Whether his Sabadilline was a definite precon- 

 tained principle or not we cannot say, not having been able to find it, 

 even in the preparation sold as being the body itself. 



In pursuance of these results, we are investigating the alkaloids of 

 V. album roots. These have been already shown by Pelletier and 

 Caventou, Simon, Mitchell, and others, to contain at least two alkaloids, 

 one being nou-sternutatory, crystallisable from alcohol, and forming very 

 sparingly soluble salts with certain mineral acids, e.g., sulphuric acid ; 

 another being non-crystalline, but powerfully sternutatory. Since both 

 the Cevadine and Veratrine above described are powerfully provocative of 

 sneezing and tickling of the throat when inhaled as dust, it would seem 

 probable that the former alkaloid, Jervine (which has never been found in 

 V. Sabadilla seeds), is utterly distinct in its nature from the latter one. 

 Our experiments, at present far from complete, lead us to believe that 

 " Jervine " is not a single alkaloid, but a mixture of two or more closely 

 alike in many respects, and quite dissimilar from the sternutatory base - r 

 whilst the latter is a mixture of bases, of which one is, if not identical 

 with the Veratrine above described, closely allied to it, as on saponification 

 the mixture forms a small quantity of Veratric acid. 



