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Merck

N3876

(−)-Nicotine

≥99% (GC), Prototype nicotinic acetylcholine receptor agonist, 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
NACRES:
NA.77
PubChem Substance ID:
24897663
UNSPSC Code:
12352210
EC Number:
200-193-3
MDL number:
MFCD00006369
Beilstein/REAXYS Number:
82109

Key Documents

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Product Name

(−)-Nicotine, ≥99% (GC), liquid

InChI key

SNICXCGAKADSCV-JTQLQIEISA-N

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

SMILES string

CN1CCC[C@H]1c2cccnc2

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.)

Quality Level

200

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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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.

General description

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

Preparation Note

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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG8270
BCCF4765
BCCD0109
BCCB8521
BCCB7027

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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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