The Aconite Alkaloids Ix. the Isolation of Two New Alkaloids from Aconitum Heterophyllum, Heteratisine and Hetisine by Walter A. Jacobs and Lyman C. Craig

In the course of the isolation of atisine from the roots of Aconitum heterophyllum of commercial origin, as presented in Paper VIII (I), it was noted that further concentration of the final mother liquors from atisine hydrochloride yielded a thick solution which on longer standing gave an additional crystalline fraction. It was then found that this fraction (10 gm. from 24 kilos of root) consisted essentially of a mixture of the hydrochlorides of two additional alkaloids. As far as it has been possible to ascertain, it appears that these alkaloids have not been previously described.l One of these formed the major portion of the above mixture and most of it was readily separated from its companion alkaloid by virtue of its sparing solubility in benzene. It crystallized very readily from alcohol as stout prisms which melted at 262-267” with decomposition and was optically active, [01]~ = f40” in methanol. The trivial name heteratisine is suggested for this alkaloid. The analytical data all conformed to the formulation C&H3,06N. The alkaloid contains one methoxyl group and an N-methyl group. No unsaturated linkage could be detected by hydrogenation. The presence of a lactone group was shown by its behavior towards alkali. On reacidification relactonization occurred. Aside from saponification of the lactone group the alkaloid did not appear to be affected by alkali. The presence of two hydroxyl groups was indicated by the Tschugaeff-Zerewitinoff determination. The hydrochloride of heteratisine was also prepared. From the above data heteratisine, like atisine, appears to be pentacyclic and this fact along with the apparent occurrence of these alkaloids in the same plant makes it probable that they are derivatives of a common pentacyclic ring system. The formulation of heteratisine and its possession of a lactone group recall in some respects observations which have been recorded with alkaloids obtained from Xtemona species; viz., the