VII.—The alkaloids of corydalis cava. Conversion of corybulbine into corydaline

James J. Dobbie, Alexander Lauder, Photios G. Paliatseas
1901 Journal of the Chemical Society Transactions  
IT has been shown in a previous paper (Trans., 1894, 65, 25) that the formula of corybulbine differs from that of corydaline by CH" and that the former alkaloid contains only three methoxyl groups, whilst the latter contains four. Having regard to this relation between the formuls of the two substances, and to the fact that corybulbine is readily soluble in caustic alkalis, in which corydaline is insoluble, and, as shown in this paper, forms an acetyl derivative, the two alkaloids would appear
more » ... loids would appear to be related to one another in the same manner as morphine, C"H"ON(OH)" and codeine, C"H"ON(OH)*OCH" corydaline being the higher homologue of corybulbine. The present paper contains a n account of the experiments by which this supposed relation was established and the one alkaloid converted into the other. When corydaline and corybulbine are treated with hydrogen iodide, the methoxyl groups which they contain are replaced by hydroxyl radicles. If corybulbine and corydaline are related to one another in the manner above suggested, the phenolic derivatives yielded by the two alkaloids should be identical. The relation of the two alkaloids to one another having been thus established, the conversion of corybulbine into corydaline by the methods formerly employed in similar cases was next successfully attempted. I n 1881, Grimaux converted morphine, C"H"ON(OH), into codeine, C1,H"ON(OH)*OCH" by treating it with methyl iodide This was found to be the case.
doi:10.1039/ct9017900087 fatcat:m3dtct4qfneste32z7f75kufu4