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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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5 ML
MXP 2,877.00
25 ML
MXP 6,407.00
100 ML
MXP 10,507.00

MXP 2,877.00

Fecha estimada de envío02 de abril de 2025

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5 ML
MXP 2,877.00
25 ML
MXP 6,407.00
100 ML
MXP 10,507.00

About This Item

Fórmula empírica (notación de Hill):
C10H14N2
Número de CAS:
54-11-5
Peso molecular:
162.23
Beilstein/REAXYS Number:
82109
EC Number:
200-193-3
MDL number:
MFCD00006369
UNSPSC Code:
12352210
PubChem Substance ID:
24897663
NACRES:
NA.77

MXP 2,877.00

Fecha estimada de envío02 de abril de 2025

Solicitar un pedido a granel

Quality Level

200

assay

≥99% (GC)

form

liquid

optical activity

[α]20/D −169°(lit.)

color

yellow

refractive index

n20/D 1.5265 (lit.)

solubility

ethanol: 50 mg/mL

density

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

InChI key

SNICXCGAKADSCV-JTQLQIEISA-N

Gene Information

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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General description

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

Application

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]

Biochem/physiol Actions

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.

Preparation Note

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

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk_germany

WGK 3

flash_point_f

213.8 °F - closed cup

flash_point_c

101 °C - closed cup

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCL8106
BCCM2475
BCCK8089
BCCH3247
BCCG8270

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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)
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. 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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