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N3876

Sigma-Aldrich

(−)-Nicotine

≥99% (GC), liquid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H14N2
CAS Number:
54-11-5
Molecular Weight:
162.23
Beilstein/REAXYS Number:
82109
EC Number:
200-193-3
MDL number:
MFCD00006369
UNSPSC Code:
12352210
PubChem Substance ID:
24897663
NACRES:
NA.77

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

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

Application

(-)-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

Biochem/physiol Actions

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.

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

Certificates of Analysis (COA)

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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)
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)
Melissa M Martin et al.
Cerebral cortex (New York, N.Y. : 1991), 30(3), 1830-1842 (2019-10-11)
Cigarette smoking during pregnancy is a major public health concern, resulting in detrimental health effects in the mother and her offspring. The adverse behavioral consequences for children include increased risk for attention deficit hyperactivity disorder, working memory deficits, epilepsy, novelty-seeking
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