Nornicotine

Nornicotine

Names
IUPAC name 3-[(2S)-2-Pyrrolidinyl]pyridine
Other names Demethylnicotine
Identifiers
CAS Number	494-97-3
3D model (Jmol)	Interactive image
ChemSpider	82588
ECHA InfoCard	100.150.375
PubChem	91462
InChI InChI=1S/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1 Key: MYKUKUCHPMASKF-VIFPVBQESA-N InChI=1/C9H12N2/c1-3-8(7-10-5-1)9-4-2-6-11-9/h1,3,5,7,9,11H,2,4,6H2/t9-/m0/s1 Key: MYKUKUCHPMASKF-VIFPVBQEBM
SMILES n1cccc(c1)[C@H]2NCCC2
Properties
Chemical formula	C9H12N2
Molar mass	148.21 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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]

${\displaystyle \mathrm {\xrightarrow[{H2O}]{Ag2O}} }$

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.

${\displaystyle \mathrm {\xrightarrow[{H2}]{Pd/C}} }$

References

1. Siminszky, B. (2005). "Conversion of nicotine to nornicotine in Nicotiana tabacum is mediated by CYP82E4, a cytochrome P450 monooxygenase". Proceedings of the National Academy of Sciences. 102 (41): 14919–24. doi:10.1073/pnas.0506581102. PMC 1253577. PMID 16192354.
2. Spaeth, Chem. Ber. 1936, 69, 250–251.
3. Haines, J. Am. Chem. Soc. 1945, 67, 1258–1260.
4. T. J. Dickerson, K. D. Janda; J. Am. Chem. Soc. 2002, 124, 13, 3220–3221; PMID 11916401.