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Merck
CN

N3876

(−)-尼古丁

≥99% (GC), Prototype nicotinic acetylcholine receptor agonist, 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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关于此项目

经验公式(希尔记法):
C10H14N2
化学文摘社编号:
分子量:
162.23
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352210
EC Number:
200-193-3
MDL number:
Beilstein/REAXYS Number:
82109
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产品名称

(−)-尼古丁, ≥99% (GC), liquid

InChI key

SNICXCGAKADSCV-JTQLQIEISA-N

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

SMILES string

CN1CCC[C@H]1c2cccnc2

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.)

Quality Level

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Application

(-)-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
  • 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
  • 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

Biochem/physiol Actions

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。它与肺癌的发展有关,并降低化疗药物的效率。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。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。尼古丁用于治疗阿尔茨海默和帕金森病。
烟碱乙酰胆碱受体激动剂原型;自然产生的异构体。

General description

烟碱是烟叶中含量最丰富的生物碱。它是一种主要的毒剂。

Preparation Note

本品应使用200 proof的纯乙醇溶解。

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

存储类别

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

wgk

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

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

    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.

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

    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.

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

    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.

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

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

  7. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

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

    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.

  10. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

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 induces neutrophil extracellular traps
Hosseinzadeh A, et al.
Journal of Leukocyte Biology, 100(5), 1105-1112 (2016)
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)
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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