N3876 Sigma-Aldrich


≥99% (GC), liquid

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

  • CAS Number 54-11-5

  • Empirical Formula (Hill Notation) C10H14N2

  • Molecular Weight 162.23

  •  Beilstein/REAXYS Number 82109

  •  EC Number 200-193-3

  •  MDL number MFCD00006369

  •  PubChem Substance ID 24897663

  •  NACRES NA.77



Related Categories Agonists, Alkaloid, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology,
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.)
Gene Information   human ... CHRNA2(1135), CHRNA3(1136), 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)


General description

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


(-)-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.

Safety & Documentation

Safety Information

Signal word 
Hazard statements 
UN 1654 6.1 / PGII
WGK Germany 
Flash Point(F) 
213.8 °F
Flash Point(C) 
101 °C


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is the concentration of Product N3876,(-)-Nicotine?
This product is not a solution.It is a liquid.The physical state of (-)-Nicotine is a liquid at room temperature.It has not been dissolved in any solvent at a specific concentration to prepare a solution.The density of (-)-Nicotine as a liquid at 20 °C is 1.010 g/mL.
What is the molarity of Product N3876,(-)-Nicotine?
The molarity of (-)-Nicotine is 6.23 M based on a 100% pure compound with a density at 20 °C equal to 1.010 g/mL.If you multiply this density by 1000, you obtain g/L.If you divide g/L by the molecular weight of (-)-Nicotine which is 162.2 g/mole, you get moles per L which is molarity.[1.010 x 1000]/162.2 = 6.23 M.
Where should Product N3876,(-)-Nicotine, be stored and what sensitivities does it have?
For long-term storage, this product can be stored at room temperature.This compound is very hygroscopic and can darken in color on exposure to air and light.
What is the difference between Nicotine, ProductsN3876 and N0267?
Prod. No. N3876 is the naturally occurring (-) isomer while Prod. No. N0267 is a mixture of the (+) and (-) isomers.
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
How can Product N3876, (-)-Nicotine, be solublized?
Product N3876, (-)-Nicotine, is soluble in ethanol.It is only miscible in water.We would recommend to solublized the product in ethanol to make a 1000x stock solution.This can then be diluted 1:1000 into aqueous buffer for use.
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Protocols & Articles


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