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N0267

Sigma-Aldrich

(±)-Nicotine

≥99% (TLC), liquid

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About This Item

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

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)

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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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Chronic 2 - Eye Dam. 1 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

213.8 °F

Flash Point(C)

101 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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