Nornicotine

It is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. Nornicotine can react in human saliva to form N-nitrosonornicotine, a known type 1 carcinogen.

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.

${\displaystyle \underset{{\mathrm{H}}_2\mathrm{O}}{\overset{\mathrm{A}{\mathrm{g}}_2\mathrm{O}}{\to }}}$

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.

${\displaystyle \underset{{\mathrm{H}}_2}{\overset{\mathrm{P}\mathrm{d}/\mathrm{C}}{\to }}}$