A Convenient Method for the Preparation of Racemic Nicotine

Abstract

Early studies, in which the first resolution of racemic nicotine was accomplished showed² that 1-nicotine, the principal alkaloid of tobacco, was acutely less toxic than d-nicotine in limited mammalian tests. Later studies^3,4 have generally confirmed this, and some investigators suggest that the physiological effects of d-nicotine may, to some extent, oppose the effects of 1-nicotine, although this matter has been debated. It has been reported⁵ that racemization of 1-nicotine during the course of tobacco smoking leads to the transfer of significant quantities of d-nicotine into the mainstream of cigarette smoke. Where d,1-nicotine has been employed in insecticidal studies, data indicate⁶ that d-nicotine-has alethality equal to that of the-1-isomer. These species differences in response to nicotine antipodes and recent evidence of a central stereospecific nicotine receptor^7,8 have stimulated inter estin efficient routes to the attainment of large quantities of-d-nicotine.