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N3876

Sigma-Aldrich

(−)-Nicotina

≥99% (GC), liquid

Sinónimos:

(−)-1-Metil-2-(3-piridil)pirrolidina, (S)-3-(1-Metil-2-pirrolidinil)piridina

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About This Item

Fórmula empírica (notación de Hill):
C10H14N2
Número de CAS:
54-11-5
Peso molecular:
162.23
Beilstein:
82109
Número CE:
200-193-3
Número MDL:
MFCD00006369
Código UNSPSC:
12352210
ID de la sustancia en PubChem:
24897663
NACRES:
NA.77
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Ensayo

≥99% (GC)

Formulario

liquid

actividad óptica

[α]20/D −169°(lit.)

color

yellow

índice de refracción

n20/D 1.5265 (lit.)

solubilidad

ethanol: 50 mg/mL

densidad

1.010 g/mL at 20 °C (lit.)

cadena SMILES

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

Clave InChI

SNICXCGAKADSCV-JTQLQIEISA-N

Información sobre el 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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Descripción general

La nicotina es el alcaloide más abundante encontrado en las hojas de las especies del género Nicotiana.[1] Es un agente tóxico importante.[2]

Aplicación

La (-)-nicotina se ha utilizado:
  • para estimular los neutrófilos en ensayos de fluorescencia de ADN extracelular y en inmunotinción de neutrófilos[2]
  • para estudiar los efectos de la exposición crónica neonatal a la nicotina en la unión al receptor nicotínico de la acetilcolina (nAChR), la muerte celular y la morfología del hipocampo y el cerebelo[3]
  • en un estudio in vitro para evaluar el efecto de la exposición radicular a la nicotina o la cotinina en la morfología y densidad de los fibroblastos[4]

Acciones bioquímicas o fisiológicas

La nicotina se une a los receptores nicotínicos de acetilcolina y exhibe efectos a la vez neuroprotectores y neurotóxicos en el cerebro en desarrollo.[3] Se asocia con el desarrollo de cáncer de pulmón y reduce la eficiencia de los quimioterápicos.[5] Además, la nicotina tiene capacidad para deteriorar la defensa fagocítica del huésped y también aumenta la lesión asociada a las especies de oxígeno reactivo (ROS).[2] También detiene la desactivación de la Akt/ proteincinasa B (PKB) y reduce la muerte espontánea de los neutrófilos.[2] La nicotina se utiliza para el tratamiento de las enfermedades de Alzheimer y de Parkinson.[6]
Receptor prototipo agonista nicotínico de la acetilcolina; isómero que se encuentra en estado natural.

Nota de preparación

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

Palabra de señalización

Danger

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

213.8 °F - closed cup

Punto de inflamabilidad (°C)

101 °C - closed cup

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCM2475
BCCL8106
BCCK8089
BCCH3247
BCCG8270

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Los clientes también vieron

Slide 1 of 1

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

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)
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)
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)
Nicotine inactivation of the proapoptotic function of Bax through phosphorylation
Xin M and Deng X
The Journal of Biological Chemistry, 280(11), 10781-10789 (2005)
Ver todos los artículos relacionados

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

    1 answer

    1. This product is not a solution.  It is a liquid.  The physical state of (-)-Nicotine is a liquid at room temperature.  It has not been dissolved in any solvent at a specific concentration to prepare a solution.  The density of (-)-Nicotine as a liquid at 20 °C is 1.010 g/mL.

      Helpful?

  7. 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?

  8. 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?

  9. 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?

  10. 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?

1–10 of 11 Questions  

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