N0267

(±)-Nicotine

≥99% (TLC), liquid

• Empirical Formula (Hill Notation): C₁₀H₁₄N₂
• CAS Number: 22083-74-5
• Molecular Weight: 162.23
• Beilstein: 82108
• MDL number: MFCD00065370
• UNSPSC Code: 12352210
• eCl@ss: 39151701
• PubChem Substance ID: 24897418
• NACRES: NA.77

Properties

• Quality Level: 200
• Assay: ≥99% (TLC)
• form: liquid
• optical activity: [α]25/D 0°(lit.)
• color: yellow
• solubility: ethanol: 50 mg/mL
• density: 1.02 g/mL at 25 °C (lit.)
• SMILES string: CN1CCCC1c2cccnc2
• 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
• InChI key: SNICXCGAKADSCV-UHFFFAOYSA-N
• Gene Information: human ... CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) ; rat ... Chrna3(25101) , Chrna4(25590) , Chrna7(25302)

Description

Application

(±)-Nicotine has been used:

• as a supplement of high-glucose Dulbecco′s modified Eagle′s medium, to test its effect on mesenchymal stem cells
• as a standard for the determination of nicotine concentration using phase high-pressure liquid chromatography
• as a test compound to study its effects on fibril formation

Biochem/physiol Actions

(±)-Nicotine is a tertiary amine compound that is predominantly present in tobacco. It binds to the nicotinic cholinergic receptors of the brain, autonomic ganglia and neuromuscular junction. Nicotine allosterically regulates a number of biological events such as production of growth hormone, dopamine, adrenocorticotropic hormone and prolactin. Nicotine absorption across biological membranes is pH sensitive, which alters its ionization state. Absorption of nicotine is shown to be higher at alkaline pH, when it remains unionized. Nicotine metabolism occurs extensively in the liver and it can cross placenta.

Prototype nicotinic acetylcholine receptor agonist.

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. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - 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