Merck
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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
Empirical Formula (Hill Notation):
C10H14N2
CAS Number:
Molecular Weight:
162.23
Beilstein:
82109
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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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.

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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