(-)-Cotinine

(-)-Cotinine is an alkaloid that has been found in tobacco plants and an active metabolite of the neuronal nicotinic acetylcholine receptor (nAChR) agonists (±)-nicotine (Cay-16535) and (-)-nicotine (Cay-29138, Cay-20887). It is formed from nicotine by the cytochrome P450 (CYP) isoforms CYP2A6 or CYP2A13 via a 5'-hydroxy nicotine intermediate. (-)-Cotinine (1 and 10 µM) reduces the number of dsDNA breaks induced by the tobacco-specific nitrosamine carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK, Cay-16414) in a comet assay using HepaRG hepatocellular carcinoma cells. In vivo, (-)-cotinine (0.09 µg/kg) increases nicotine self-administration in rats.Formal Name: 1-methyl-5S-(3-pyridinyl)-2-pyrrolidinone. CAS Number: 486-56-6. Synonyms: NIH 10498. Molecular Formula: C10H12N2O. Formula Weight: 176.2. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, Ethanol: 30 mg/ml, PBS (pH 7.2): 10 mg/ml. lambdamax: 262 nm. SMILES: O=C1CC[C@@H](C2=CN=CC=C2)N1C. InChi Code: InChI=1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1. InChi Key: UIKROCXWUNQSPJ-VIFPVBQESA-N. Origin: Synthetic.