Merck
Todas as fotos(1)

N3876

Sigma-Aldrich

(−)-Nicotine

≥99% (GC), liquid

Todas as fotos(1)
Sinônimo(s):
(−)-1-Methyl-2-(3-pyridyl)pyrrolidine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine
Empirical Formula (Hill Notation):
C10H14N2
Número CAS:
54-11-5
Peso molecular:
162.23
Beilstein:
82109
Número EC:
200-193-3
Número MDL:
MFCD00006369
ID de substância PubChem:
24897663
NACRES:
NA.77

Nível de qualidade

200

teor

≥99% (GC)

forma

liquid

atividade óptica

[α]20/D −169°(lit.)

cor

yellow

índice de refração

n20/D 1.5265 (lit.)

solubilidade

ethanol: 50 mg/mL

densidade

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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Descrição geral

Nicotine is the most abundant alkaloid found in the leaves of Nicotiana species. It is a major toxic agent.

Aplicação

(-)-Nicotine has been used:
  • to stimulate neutrophils in extracellular DNA fluorescence assay and in immunostaining of neutrophils
  • to study the effects of chronic neonatal nicotine exposure on nicotinic acetylcholine receptor (nAChR) binding, cell death and morphology in hippocampus and cerebellum
  • in an in vitro study to evaluate the effect of root exposure to nicotine or cotinine on the morphology and density of fibroblasts

Ações bioquímicas/fisiológicas

Nicotine binds to nicotinic acetylcholine receptors and exhibit both neuroprotective and neurotoxic effects on the developing brain. It is associated with lung cancer development and reduces the efficiency of chemotherapeutic agents. In addition, nicotine has an ability to impair phagocytic host defense and also increase reactive oxygen species (ROS) associated injury. It also stops Akt/ protein kinase B (PKB) deactivation and decreases spontaneous death of neutrophils. Nicotine is used to treat Alzheimer′s and Parkinson′s disease.
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Palavra indicadora

Danger

Classificações de perigo

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

Código de classe de armazenamento

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

WGK

WGK 3

Ponto de fulgor (ºF)

231.8 °F

Ponto de fulgor (ºC)

111 °C

Equipamento de proteção individual

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

Certificado de análise

Insira o número de lote para pesquisar o Certificado de análise (COA).

Certificado de origem

Insira o número de lote para pesquisar o Certificado de origem (COO).

Mais documentos

FT-IR Condensed Phase
FT-NMR Spectra
Novel neuronal nicotinic acetylcholine receptor agonist
Spectra - ATR-IR
Spectra for FT-IR Raman
Structure Search

Quotes and Ordering

Bulk Quote-Order Product

  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.

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 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)
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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