Nornicotine is an alkaloid with the formula NC5H4−C4H7NH. A colorless oil, it is a significant alkaloid in Nicotiana, the tobacco plant, although less abundant than nicotine. It is structurally similar to nicotine but does not contain a methyl group.
Biochemical processes In nature, nornicotine is produced by demethylation of nicotine. This process, which requires oxygen, is catalyzed by nicotine N-demethylase, a cytochrome P450. nornicotine 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.
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.
Nornicotine was first synthesized from nicotine-N-oxide.
Pharmacology Nornicotine possess high affinity for alpha-6 and alpha-7 subunits of nAChRs. It also inhibits DAT in striatum via nAChR and releases dopamine in rats.
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