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Merck

N0267

Sigma-Aldrich

(±)-Nikotin

≥99% (TLC), liquid

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About This Item

Empirische Formel (Hill-System):
C10H14N2
CAS-Nummer:
Molekulargewicht:
162.23
Beilstein:
82108
MDL-Nummer:
UNSPSC-Code:
12352210
eCl@ss:
39151701
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥99% (TLC)

Form

liquid

Optische Aktivität

[α]25/D 0°(lit.)

Farbe

yellow

Löslichkeit

ethanol: 50 mg/mL

Dichte

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

InChIKey

SNICXCGAKADSCV-UHFFFAOYSA-N

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Anwendung

(±)-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. Wirkung

(±)-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.

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

213.8 °F - closed cup

Flammpunkt (°C)

101 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Analysenzertifikate (COA)

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Alterations in the production and concentration of selected alkaloids as a function of rising atmospheric carbon dioxide and air temperature: implications for ethno-pharmacology
Ziska LH, et al.
Global Change Biology, 11(10), 1798-1807 (2005)
Neal L Benowitz
Nicotine Safety and Toxicity, 3-7 (1998)
The effect of nicotine on the mechanical properties of mesenchymal stem cells
Ruiz JP, et al.
Cell health and cytoskeleton, 4, 29-29 (2012)
W Sihver et al.
Neuroscience, 94(3), 685-696 (1999-12-01)
The laminar binding distribution of three nicotinic receptor agonists, [3H](-)nicotine, [3H]cytisine, and [3H]epibatidine, and their relation to the [3H]vesamicol binding, which is known to represent the vesicular acetylcholine transport sites, was performed employing in vitro autoradiography on the medial temporal
Monica E Cornelius et al.
Tobacco control, 24 Suppl 3, iii4-iii10 (2014-06-12)
This paper examines trends in cigarette prices and corresponding purchasing patterns over a 9-year period and explores characteristics associated with the quantity and location of cigarettes purchased by adult smokers in the USA. The data for this paper come from

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