(R,S)-Nornicotine

• CAT Number: R000337
• CAS Number: 5746-86-1
• Molecular Formula: C9H12N2
• Molecular Weight: 148.209
• Purity: ≥95%
• Synonyms: 3-(2-Pyrrolidinyl)pyridine; (±)-1’-Demethylnicotine; (±)-3-(2-Pyrrolidinyl)pyridine; (±)-1’-Demethylnicotine; (±)-Nornicotine; 2-(3-Pyridinyl)pyrrolidine; 3-(Pyrrolidin-2-yl)pyridine; ?
• Storage: -20°C
• IUPAC Name: 3-pyrrolidin-2-ylpyridine
• 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
• InChIKey: MYKUKUCHPMASKF-UHFFFAOYSA-N
• SMILES: C1CC(NC1)C2=CN=CC=C2

(±)-Nornicotine is a metabolite of nicotine (Item No. 16535) that acts as a neuronal nicotinic acetylcholine receptor (nAChR) agonist. The α6 and α7 subunit-containing neuronal nAChRs are particularly responsive to nornicotine with EC50 values of approximately 4 and 17 µM, respectively, when expressed in Xenopus oocytes. Nornicotine promotes cell migration and destabilizes cell-cell junctions in an endothelial cell line. It is generally thought to be free from abuse potential, but it has been self-administered by rats. It can be detected in urine.