(±)-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<sub>i</sub>s = 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.
| Catalog Number | R000840 |
| CAS Number | 22083-74-5 |
| 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; |
| Molecular Formula | C10H14N2 |
| Purity | 95% |
| 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 |
