N3876

(−)-Nicotine

≥99% (GC), liquid

• Synonym(s): (−)-1-Methyl-2-(3-pyridyl)pyrrolidine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
• Empirical Formula (Hill Notation): C₁₀H₁₄N₂
• CAS Number: 54-11-5
• Molecular Weight: 162.23
• Beilstein/REAXYS Number: 82109
• EC Number: 200-193-3
• MDL number: MFCD00006369
• UNSPSC Code: 12352210
• PubChem Substance ID: 24897663
• NACRES: NA.77

Properties

• assay: ≥99% (GC)
• form: liquid
• optical activity: [α]20/D −169°(lit.)
• color: yellow
• refractive index: n20/D 1.5265 (lit.)
• solubility: ethanol: 50 mg/mL
• density: 1.010 g/mL at 20 °C (lit.)
• SMILES string: CN1CCC[C@H]1c2cccnc2
• 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/t10-/m0/s1
• InChI key: SNICXCGAKADSCV-JTQLQIEISA-N
• Gene Information: human ... CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) , CHRNB2(1141) , CHRNB4(1143) , CYP2A6(1548) , KCNH1(3756) ; mouse ... Chrna7(11441) , Chrnb1(11443) ; rat ... Chrna1(79557) , Chrna2(170945) , Chrna4(25590) , Chrna7(25302) , Chrnb2(54239) , Chrnb4(25103)

Description

General description

Nicotine is the most abundant alkaloid found in the leaves of Nicotiana species. It is a major toxic agent.

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.

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Safety Information

• pictograms: GHS06,GHS05,GHS09
• signalword: Danger
• hcodes: H300 + H310 + H330,H315,H318,H411
• pcodes: P262 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2
• Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 213.8 °F - closed cup
• flash_point_c: 101 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter