(−)-Nicotine
SIGMA/N3876 - ≥99% (GC), liquid
Synonym: (−)-1-Methyl-2-(3-pyridyl)pyrrolidine; (S)
CAS Number: 54-11-5
Empirical Formula (Hill Notation): C10H14N2
Molecular Weight: 162.23
EC Number: 200-193-3
MDL Number: MFCD00006369
Linear Formula: C10H14N2
Product Type: Chemical
| assay | ≥99% (GC) |
| color | yellow |
| density | 1.010 g/mL at 20 °C (lit.) |
| form | liquid |
| InChI | 1S/C10H14N2/c1-12-7-3-5-1 |
| InChI key | SNICXCGAKADSCV-JTQLQIEISA |
| optical activity | [α]20/D −169°(lit.) |
| Quality Level | 200  |
| refractive index | n |
| SMILES string | CN1CCC[C@H]1c2cccnc2 |
| solubility | ethanol: 50 mg/mL |
| Application: | (-)-Nicotine has been used: • to stimulate neutrophils in extracellular DNA fluorescence assay and in immunostaining of neutrophils • to study the effects of chronic neonatal nicotine exposure on nicotinic acetylcholine receptor (nAChR) binding, cell death and morphology in hippocampus and cerebellum • in an in vitro study to evaluate the effect of root exposure to nicotine or cotinine on the morphology and density of fibroblasts |
| Biochem/physiol Actions: | Nicotine binds to nicotinic acetylcholine receptors and exhibit both neuroprotective and neurotoxic effects on the developing brain. It is associated with lung cancer development and reduces the efficiency of chemotherapeutic agents. In addition, nicotine has an ability to impair phagocytic host defense and also increase reactive oxygen species (ROS) associated injury. It also stops Akt/ protein kinase B (PKB) deactivation and decreases spontaneous death of neutrophils. Nicotine is used to treat Alzheimer′s and Parkinson′s disease. |
| Biochem/physiol Actions: | Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer. |
| General description: | Nicotine is the most abundant alkaloid found in the leaves of Nicotiana species. It is a major toxic agent. |
| Preparation Note: | This product should be dissolved in 200 proof, pure ethanol. |
| Symbol |    GHS05,GHS06,GHS09 |
| Signal word | Danger |
| Hazard statements | H300 + H310 + H330 - H315 - H318 - H411 |
| Precautionary statements | P262 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310 - P305 + P351 + P338 |
| Hazard Codes | T+,N |
| Risk Statements | 25-27-51/53 |
| Safety Statements | 36/37-45-61 |
| RIDADR | UN 1654 6.1 / PGII |
| WGK Germany | WGK 3 |
| Flash Point(F) | 231.8 °F |
| Flash Point(C) | 111 °C |
| Purity | ≥99% (GC) |
| Density | 1.010 g/mL at 20 °C (lit.) |
| Refractive Index | n |
| UNSPSC | 12352210 |