Key Documents

View All Documentation

N3876

(−)-Nicotine

Name: (&#8722;)-Nicotine
Brand: SIGMA

≥99% (GC), Prototype nicotinic acetylcholine receptor agonist, liquid

Synonym(s):

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

Select a Size

Change View

About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₄N₂

CAS Number:

54-11-5

Molecular Weight:

162.23

NACRES:

NA.77

PubChem Substance ID:

24897663

UNSPSC Code:

12352210

EC Number:

200-193-3

MDL number:

MFCD00006369

Beilstein/REAXYS Number:

82109

Assay:

≥99% (GC)

Form:

liquid

Quality level:

200

Technical Service

Need help? Our team of experienced scientists is here for you.

Let Us Assist

Properties

Product Name

(−)-Nicotine, ≥99% (GC), liquid

Quality Level

200

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)

Description

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

Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

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.