(±)-Nicotine-d₃is intended for use as an internal standard for the quantification of (±)-nicotine by GC- or LC-mass spectrometry. (±)-Nicotine is the racemic mixture of the dominant alkaloid found in tobacco plants. It acts as an agonist at neuronal nicotinic acetylcholine receptors (nAChRs; K_is = 481 and 11.1 nM for α3β4 and α4β2 subtypes, respectively) and possesses addictive and teratogenic properties.¹(-)-(S)-Nicotine is significantly more active at binding nAChRs compared to the (+)-(R) antipode, thus nicotine is typically synthesized as (-)-(S)-nicotine with only 0.2-1% of the (+)-(R) isomer present.²

1.Zaveri, N., Jiang, F., Olsen, C., et al.Novel α3β4 nicotinic acetylcholine receptor-selective ligands. Discovery, structure-activity studies, and pharmacological evaluationJ. Med. Chem.53(22)8187-8191(2010) 2.Clayton, P., Lu, A., and Bishop, L.The pyrolysis of (-)-(S)-nicotine: Racemization and decompositionChirality22(4)442-446(2010)