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Merck

N3876

Sigma-Aldrich

(−)-尼古丁

≥99% (GC), liquid

别名:

(−)-1-甲基-2-(3-吡啶基)四氢吡咯, (S)-3-(1-甲基-2-吡咯烷基)吡啶

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About This Item

经验公式(希尔记法):
C10H14N2
CAS号:
分子量:
162.23
Beilstein:
82109
EC 号:
MDL编号:
UNSPSC代码:
12352210
PubChem化学物质编号:
NACRES:
NA.77
价格与库存信息目前不能提供

方案

≥99% (GC)

表单

liquid

旋光性

[α]20/D −169°(lit.)

颜色

yellow

折射率

n20/D 1.5265 (lit.)

溶解性

ethanol: 50 mg/mL

密度

1.010 g/mL at 20 °C (lit.)

SMILES字符串

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

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一般描述

烟碱是烟叶中含量最丰富的生物碱。[1]它是一种主要的毒剂。[2]

应用

(-)-尼古丁已被用于:
  • 在细胞外DNA荧光实验和中性粒细胞免疫染色中刺激中性粒细胞[2]
  • 通过细胞外DNA荧光检测和中性粒细胞免疫染色来研究新生儿慢性尼古丁暴露对尼古丁乙酰胆碱受体(nAChR)结合、细胞死亡和海马和小脑形态的影响[3]
  • 在体外研究中评估尼古丁或可替宁的根暴露对成纤维细胞形态和密度的影响[4]

生化/生理作用

尼古丁与尼古丁乙酰胆碱受体结合,对发育中的大脑既有神经保护作用又有神经毒性作用。[3]它与肺癌的发展有关,并降低化疗药物的效率。[5]此外,尼古丁还具有损害吞噬细胞宿主防御的能力,并增加活性氧(ROS)相关损伤。[2]它还能阻止Akt/蛋白激酶B (PKB)的失活,减少中性粒细胞的自发死亡。[2]尼古丁用于治疗阿尔茨海默和帕金森病。[6]
烟碱乙酰胆碱受体激动剂原型;自然产生的异构体。

制备说明

本品应使用200 proof的纯乙醇溶解。

警示用语:

Danger

危险分类

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

储存分类代码

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

WGK

WGK 3

闪点(°F)

213.8 °F - closed cup

闪点(°C)

101 °C - closed cup

个人防护装备

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


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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其他客户在看

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)
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)

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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