N3876

(−)-Nicotine

≥99% (GC), 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
• Numéro Beilstein : 82109
• Numéro CE : 200-193-3
• Numéro MDL: MFCD00006369
• Code UNSPSC : 12352210
• ID de substance PubChem : 24897663
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥99% (GC)
• Forme: liquid
• Activité optique: [α]20/D −169°(lit.)
• Couleur: yellow
• Indice de réfraction: n20/D 1.5265 (lit.)
• Solubilité: ethanol: 50 mg/mL
• Densité: 1.010 g/mL at 20 °C (lit.)
• Chaîne SMILES: 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
• Clé InChI: SNICXCGAKADSCV-JTQLQIEISA-N
• Informations sur le gène: 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

Description générale

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

Actions biochimiques/physiologiques

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.

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

Informations sur la sécurité

• Pictogrammes: GHS06,GHS05,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H300 + H310 + H330,H315,H318,H411
• Conseils de prudence: P262 - P273 - P280 - P302 + P352 + P310 - P304 + P340 + P310 - P305 + P351 + P338
• Classification des risques: Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2
• Code de la classe de stockage: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): 213.8 °F - closed cup
• Point d'éclair (°C): 101 °C - closed cup
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter