N3876

(−)-Nicotine

≥99% (GC), Prototype nicotinic acetylcholine receptor agonist, liquid

• Synonyme(s) : (−)-1-Methyl-2-(3-pyridyl)pyrrolidine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
• Formule empirique (notation de Hill) : C₁₀H₁₄N₂
• Numéro CAS: 54-11-5
• Poids moléculaire : 162.23
• NACRES: NA.77
• PubChem Substance ID: 24897663
• UNSPSC Code: 12352210
• EC Number: 200-193-3
• MDL number: MFCD00006369
• Beilstein/REAXYS Number: 82109
• Assay: ≥99% (GC)
• Form: liquid

Propriétés

• Nom du produit: (−)-Nicotine, ≥99% (GC), liquid
• Quality Segment: 200
• 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

Agonist prototype nicotinique du récepteur de l′acétylcholine; isomère naturel

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.

Preparation Note

This product should be dissolved in 200 proof, pure ethanol.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS05,GHS09
• Mot-clé: Danger
• Codes de danger: H300 + H310 + H330,H315,H318,H411
• Mentions de précaution: 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
• Classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Point d'éclair (°F): 213.8 °F - closed cup
• Point d'éclair (°C): 101 °C - closed cup
• EPI (équipement de protection individuelle): Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter