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Key Documents

N3876

Sigma-Aldrich

(−)-Nicotine

≥99% (GC), liquid

Sinônimo(s):

(−)-1-Methyl-2-(3-pyridyl)pyrrolidine, (S)-3-(1-Methyl-2-pyrrolidinyl)pyridine

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About This Item

Fórmula empírica (Notação de Hill):
C10H14N2
Número CAS:
Peso molecular:
162.23
Beilstein:
82109
Número CE:
Número MDL:
Código UNSPSC:
12352210
ID de substância PubChem:
NACRES:
NA.77

Nível de qualidade

Ensaio

≥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.)

cadeia de caracteres 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

chave InChI

SNICXCGAKADSCV-JTQLQIEISA-N

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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.

Nota de preparo

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

Palavra indicadora

Danger

Classificações de perigo

Acute Tox. 1 Oral - Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - 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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

213.8 °F - closed cup

Ponto de fulgor (°C)

101 °C - closed cup

Equipamento de proteção individual

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


Certificados de análise (COA)

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Encontre a documentação dos produtos que você adquiriu recentemente na biblioteca de documentos.

Visite a Biblioteca 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)

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