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N3876

Sigma-Aldrich

(−)-Nikotin

≥99% (GC), liquid

Synonym(e):

(−)-1-Methyl-2-(3-pyridyl)pyrrolidin, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridin, L-(−)-3-(N-Methyl)-α-pyrrolidyl)-pyridin

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About This Item

Empirische Formel (Hill-System):
C10H14N2
CAS-Nummer:
54-11-5
Molekulargewicht:
162.23
Beilstein:
82109
EG-Nummer:
200-193-3
MDL-Nummer:
MFCD00006369
UNSPSC-Code:
12352210
PubChem Substanz-ID:
24897663
NACRES:
NA.77
Preise und Verfügbarkeit sind derzeit nicht verfügbar.

Qualitätsniveau

200

Assay

≥99% (GC)

Form

liquid

Optische Aktivität

[α]20/D −169°(lit.)

Farbe

yellow

Brechungsindex

n20/D 1.5265 (lit.)

Löslichkeit

ethanol: 50 mg/mL

Dichte

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

InChIKey

SNICXCGAKADSCV-JTQLQIEISA-N

Angaben zum Gen

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)

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Allgemeine Beschreibung

Nikotin ist das in den Blättern der Nicotiana-Spezies am häufigsten vorkommende Alkaloid.[1] Es ist ein wichtiger toxischer Wirkstoff.[2]

Anwendung

(-)-Nikotin wird verwendet:
  • zur Stimulierung von Neutrophilen im extrazellulären DNA-Fluoreszenztest und bei der Immunfärbung von Neutrophilen[2]
  • zur Untersuchung der Auswirkungen der chronischen Nikotinexposition von Neugeborenen auf die Nikotin-Acetylcholinrezeptor(nAChR)-Bindung, den Zelltod und die Morphologie im Hippocampus und Kleinhirn[3]
  • in einer In-vitro-Studie zur Bewertung der Wirkung einer Wurzelexposition gegenüber Nikotin oder Cotinin auf die Morphologie und Dichte von Fibroblasten[4]

Biochem./physiol. Wirkung

Nikotin bindet an nikotinische Acetylcholinrezeptoren und zeigt sowohl neuroprotektive als auch neurotoxische Wirkungen auf das sich entwickelnde Gehirn.[3] Es wird mit der Entwicklung von Lungenkrebs in Verbindung gebracht und verringert die Wirksamkeit von Chemotherapeutika.[5] Darüber hinaus kann Nikotin die phagozytäre Wirtsabwehr beeinträchtigen und zu vermehrten, mit reaktiven Sauerstoffspezies (ROS) verbundenen Verletzungen führen.[2] Es stoppt zudem die Deaktivierung der Akt/Proteinkinase B (PKB) und verringert den spontanen Tod von Neutrophilen.[2] Nikotin wird zur Behandlung von Alzheimer und Parkinson eingesetzt.[6]
Prototyp Nikotin-Acetylcholin-Rezeptor-Agonist; natürlich vorkommendes Isomer.

Angaben zur Herstellung

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

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - 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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCM2475
BCCL8106
BCCK8089
BCCH3247
BCCG8270

Die passende Version wird nicht angezeigt?

Wenn Sie eine bestimmte Version benötigen, können Sie anhand der Lot- oder Chargennummer nach einem spezifischen Zertifikat suchen.

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1 of 1

(±)-Nicotine-d4 solution 100 μg/mL in acetonitrile, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

N-048

(±)-Nicotine-d4 solution

Nicotine alkaloid levels, and nicotine to nornicotine conversion, in Australian Nicotiana species used as chewing tobacco
Moghbel N, et al.
Heliyon, 3(11), e00469-e00469 (2017)
Effects of chronic neonatal nicotine exposure on nicotinic acetylcholine receptor binding, cell death and morphology in hippocampus and cerebellum
Huang LZ, et al.
Neuroscience, 146(4), 1854-1868 (2007)
Root surface conditioning with nicotine or cotinine reduces viability and density of fibroblasts in vitro
Martinez AE, et al.
Clinical Oral Investigations, 9(3), 180-186 (2005)
Nicotine induces neutrophil extracellular traps
Hosseinzadeh A, et al.
Journal of Leukocyte Biology, 100(5), 1105-1112 (2016)
Chronic nicotine exposure differentially affects the function of human alpha3, alpha4, and alpha7 neuronal nicotinic receptor subtypes
Olale F, et al.
Journal of Pharmacology and Experimental Therapeutics, 283(2), 675-683 (1997)
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Questions

1–10 of 11 Questions  

  1. Is product N3876 (-)-Nicotine considered freebase nicotine or a nicotine salt dissolved in a carrier liquid

    1 answer

    1. This product is nicotine free base and is provided in the form of a neat or pure liquid.

      Helpful?

  2. Hi , How i want to measure the purity level of nicotine? Can refractive index or polarimeter use to measure level of impurity?

    1 answer

    1. The measurement of purity in nicotine can be assessed using various analytical techniques. Refractive index and polarimetry are among the methods that can provide useful information. However, it's important to note that these techniques may not directly measure specific impurities but can be indicative of changes in the overall composition or characteristics of a substance. The purity of this product is determined by GC. Gas Chromatography (GC) is a widely used and effective method for assessing the purity of nicotine and detecting impurities. GC separates and analyzes components based on their volatility and interaction with a stationary phase.

      Please access a Certificate of Analysis in the DOCUMENTATION section for reference:
      https://www.sigmaaldrich.com/product/sigma/n3876#product-documentation

      Helpful?

  3. Hello, I would like to know the concentration of the nicotine in this liquid solution.

    1 answer

    1. This product is a neat or pure liquid. Based on the density of 1.02 g/mL and the molecular weight of 162.2 g/mole, the calculated molar concentration is 6.3 M.

      Helpful?

  4. How long is the nicotine stable if stored at room temperature? How long is it stable after being dssiolved and how should the solution be stored?

    1 answer

    1. This compound is stored at room temperature, but is extremely sensitive to light, moisture, and oxygen. The product is a neat liquid and packaged in amber glass under argon to preserve stability. In the unopened container, the product is stable at least until the recommended retest date reported on the lot specific Certificate of Analysis. This date is typically 3 years from the quality release date. Factors such as light, humidity, and exposure to air will limit the shelf life after opening, It is recommended to prepare solutions fresh. The vial head space should be cleared with argon or nitrogen prior to closing. Increased darkening of the material is an indication of product degradation. Please see the link below to review a sample Certificate of Analysis:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/N3876-BULKBCCK8089.pdf

      Helpful?

  5. what % of ethanol should be used to be solublized?

    1 answer

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

      Helpful?

  6. Where should Product N3876, (-)-Nicotine, be stored and what sensitivities does it have?

    1 answer

    1. For long-term storage, this product can be stored at room temperature.  This compound is very hygroscopic and can darken in color on exposure to air and light.

      Helpful?

  7. What is the difference between Nicotine, Products N3876 and N0267?

    1 answer

    1. Prod. No. N3876 is the naturally occurring (-) isomer while Prod. No. N0267 is a mixture of the (+) and (-) isomers.

      Helpful?

  8. What is the molarity of Product N3876,  (-)-Nicotine?

    1 answer

    1. The molarity of (-)-Nicotine is 6.23 M based on a 100% pure compound with a density at 20 °C equal to 1.010 g/mL.  If you multiply this density by 1000, you obtain g/L.  If you divide g/L by the molecular weight of (-)-Nicotine which is 162.2 g/mole, you get moles per L which is molarity.  [1.010 x 1000]/162.2 = 6.23 M.

      Helpful?

  9. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

      Helpful?

  10. How can Product N3876, (-)-Nicotine, be solublized?

    1 answer

    1. Product N3876, (-)-Nicotine, is soluble in ethanol.  It is only miscible in water.  We would recommend to solublized the product in ethanol to make a 1000x stock solution.  This can then be diluted 1:1000 into aqueous buffer for use.

      Helpful?

1–10 of 11 Questions  

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