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: 82109
• EC Number: 200-193-3
• MDL number: MFCD00006369
• UNSPSC Code: 12352210
• PubChem Substance ID: 24897663
• NACRES: NA.77

Properties

• Quality Level: 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.[1] It is a major toxic agent.[2]

Application

(-)-Nicotine has been used:

• to stimulate neutrophils in extracellular DNA fluorescence assay and in immunostaining of neutrophils[2]
• to study the effects of chronic neonatal nicotine exposure on nicotinic acetylcholine receptor (nAChR) binding, cell death and morphology in hippocampus and cerebellum[3]
• in an in vitro study to evaluate the effect of root exposure to nicotine or cotinine on the morphology and density of fibroblasts[4]

Biochem/physiol Actions

Nicotine binds to nicotinic acetylcholine receptors and exhibit both neuroprotective and neurotoxic effects on the developing brain.[3] It is associated with lung cancer development and reduces the efficiency of chemotherapeutic agents.[5] In addition, nicotine has an ability to impair phagocytic host defense and also increase reactive oxygen species (ROS) associated injury.[2] It also stops Akt/ protein kinase B (PKB) deactivation and decreases spontaneous death of neutrophils.[2] Nicotine is used to treat Alzheimer′s and Parkinson′s disease.[6]

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Preparation Note

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

Safety Information

• Pictograms: GHS06,GHS05,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 Classifications: Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2
• Storage Class Code: 6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
• WGK: WGK 3
• Flash Point(F): 213.8 °F - closed cup
• Flash Point(C): 101 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves