Nornicotine


Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant. It is chemically similar to nicotine, but does not contain a methyl group.
It is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco.

Synthesis

There are several routes for the synthesis of nornicotine. One route is the demethylation of nicotine, which can be accomplished by reaction with silver oxide.

Another route is the partial reduction of 3-myosmine, which can be accomplished by standard catalytic hydrogenation conditions using palladium as a catalyst or with sodium borohydride. This reaction gives the racemic product.