Nornicotine
Chemical compound
From Wikipedia, the free encyclopedia
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.[1] It is structurally similar to nicotine but does not contain a methyl group.
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| Names | |
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| IUPAC name
3-[(2S)-2-Pyrrolidinyl]pyridine | |
| Other names
Demethylnicotine | |
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.165.066 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C9H12N2 | |
| Molar mass | 148.209 g·mol−1 |
| Appearance | colorless oil |
| Density | 1.044 g/cm3 |
| Boiling point | 111 °C (232 °F; 384 K) 3 mm Hg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1]
nornicotine is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco.[2] Nornicotine can react in human saliva to form N-nitrosonornicotine,[3] a known type 1 carcinogen.[4]
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.[5]
![{\displaystyle \mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}} }](http://wikimedia.org/api/rest_v1/media/math/render/svg/9e72a53e3814d3819989e4e6930a8e893b9c4225)
Another route is the partial reduction of 3-myosmine, which can be accomplished by standard catalytic hydrogenation conditions using palladium as a catalyst[6] or with sodium borohydride.[7] This reaction gives the racemic product.
![{\displaystyle \mathrm {\xrightarrow[{H_{2}}]{Pd/C}} }](http://wikimedia.org/api/rest_v1/media/math/render/svg/efcf2036dece0161b4b1d5ffa6b0cbb27c449668)
Nornicotine was first synthesized from nicotine-N-oxide.[8]