Nornicotine

Nornicotine is an alkaloid found in various plants including Nicotiana, the tobacco plant.^[1] It is chemically similar to nicotine, but does not contain a methyl group.

Nornicotine

Names
IUPAC name 3-[(2S)-2-Pyrrolidinyl]pyridine
Other names Demethylnicotine
Identifiers
CAS Number	494-97-3 Y
3D model (JSmol)	Interactive image
ChemSpider	82588
ECHA InfoCard	100.165.066
PubChem CID	91462
UNII	83H6L5QD8Z Y
CompTox Dashboard (EPA)	DTXSID50862034
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	148.209 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

It 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]

${\displaystyle \mathrm {\xrightarrow[{H_{2}O}]{Ag_{2}O}} }$

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.

${\displaystyle \mathrm {\xrightarrow[{H_{2}}]{Pd/C}} }$

Pharmacology

Nornicotine possess high affinity for alpha-6 and alpha-7 subunits of nAChRs.^[8] It also inhibits DAT in striatum via nAChR and releases dopamine in rats.^[9][10][11]