Nornicotine
From Infogalactic: the planetary knowledge core
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Names | |
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IUPAC name
3-[(2S)-2-Pyrrolidinyl]pyridine
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Other names
Demethylnicotine
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Identifiers | |
494-97-3 | |
ChemSpider | 82588 |
Jmol 3D model | Interactive image |
PubChem | 91462 |
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Properties | |
C9H12N2 | |
Molar mass | 148.21 g·mol−1 |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
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.[1]
Synthesis
For the synthesis of nornicotine several paths can be taken. This includes the demethylation of nicotine. The removal of the methyl group can be accomplished for example by reaction with silver oxide.[2]
![\mathrm{ \xrightarrow[H2O]{Ag2O} }](/w/images/math/1/f/4/1f4ef0ec4a8b7f870f5699906877e4b7.png)
The reduction of 3-myosmine for example with molecular hydrogen on palladium-carbon catalyst[3] or with sodium borohydride[4] provides (±) -Nornicotin in moderate to good yields.
![\mathrm{ \xrightarrow[H2]{Pd/C} }](/w/images/math/b/0/d/b0dfc80246ca40471e78a1eeb11b877a.png)
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Spaeth, Chem. Ber. 1936, 69, 250–251.
- ↑ Haines, J. Am. Chem. Soc. 1945, 67, 1258–1260.
- ↑ T. J. Dickerson, K. D. Janda; J. Am. Chem. Soc. 2002, 124, 13, 3220–3221; PMID 11916401.
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- Alkaloids
- Pyridines
- Pyrrolidines
- Alkaloids found in Nicotiana
- Heterocyclic compound stubs