rac-Nicotine

• CAT Number: R000840
• CAS Number: 22083-74-5
• Molecular Formula: C10H14N2
• Molecular Weight: 162.236
• Purity: ≥95%
• Synonyms: 3-(1-Methyl-2-pyrrolidinyl)pyridine; (±)-Nicotine; (±)-3-(1-Methyl-2-pyrrolidinyl)pyridine; (R,S)-Nicotine; (±)-Nicotine; 1-Methyl-2-(3-pyridyl)pyrrolidine; DL-Nicotine
• Storage: -20°C
• IUPAC Name: 3-(1-methylpyrrolidin-2-yl)pyridine
• InChI: InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3
• InChIKey: SNICXCGAKADSCV-UHFFFAOYSA-N
• SMILES: CN1CCCC1C2=CN=CC=C2

(±)-Nicotine is the racemic mixture of the dominant alkaloid found in tobacco plants. It acts as an agonist at neuronal nicotinic acetylcholine receptors (nAChRs; Kis = 481 and 11.1 nM for α3β4 and α4β2 subtypes, respectively) and possesses addictive and teratogenic properties. (−)-(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.