Nornicotine

Nornicotine

Names
IUPAC name 3-[(2S)-2-Pyrrolidinyl]pyridine
Other names Demethylnicotine
Identifiers
CAS Number	494-97-3
3D model (JSmol)	Interactive image
ChemSpider	82588
ECHA InfoCard	100.165.066
PubChem CID	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.

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.