Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

N3876

Sigma-Aldrich

(−)-Nicotine

≥99% (GC), liquid

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H14N2
CAS Number:
54-11-5
Molecular Weight:
162.23
Beilstein:
82109
EC Number:
200-193-3
MDL number:
MFCD00006369
UNSPSC Code:
12352210
PubChem Substance ID:
24897663
NACRES:
NA.77
Pricing and availability is not currently available.

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)

Looking for similar products? Visit Product Comparison Guide

General description

Nicotine is the most abundant alkaloid found in the leaves of Nicotiana species.[1] It is a major toxic agent.[2]

Application

(-)-Nicotine has been used:
  • to stimulate neutrophils in extracellular DNA fluorescence assay and in immunostaining of neutrophils[2]
  • to study the effects of chronic neonatal nicotine exposure on nicotinic acetylcholine receptor (nAChR) binding, cell death and morphology in hippocampus and cerebellum[3]
  • in an in vitro study to evaluate the effect of root exposure to nicotine or cotinine on the morphology and density of fibroblasts[4]

Biochem/physiol Actions

Nicotine binds to nicotinic acetylcholine receptors and exhibit both neuroprotective and neurotoxic effects on the developing brain.[3] It is associated with lung cancer development and reduces the efficiency of chemotherapeutic agents.[5] In addition, nicotine has an ability to impair phagocytic host defense and also increase reactive oxygen species (ROS) associated injury.[2] It also stops Akt/ protein kinase B (PKB) deactivation and decreases spontaneous death of neutrophils.[2] Nicotine is used to treat Alzheimer′s and Parkinson′s disease.[6]
Prototype nicotinic acetylcholine receptor agonist; naturally occurring isomer.

Preparation Note

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

Signal Word

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 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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BCCL8106
BCCM2475
BCCK8089
BCCH3247
BCCG8270

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

(±)-Nicotine-d4 solution 100 μg/mL in acetonitrile, ampule of 1 mL, certified reference material, Cerilliant®

Supelco

N-048

(±)-Nicotine-d4 solution

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 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)
Chronic nicotine exposure differentially affects the function of human alpha3, alpha4, and alpha7 neuronal nicotinic receptor subtypes
Olale F, et al.
Journal of Pharmacology and Experimental Therapeutics, 283(2), 675-683 (1997)
View All Related Papers

Questions

1–10 of 11 Questions  

  1. Is product N3876 (-)-Nicotine considered freebase nicotine or a nicotine salt dissolved in a carrier liquid

    1 answer

    1. This product is nicotine free base and is provided in the form of a neat or pure liquid.

      Helpful?

  2. Hi , How i want to measure the purity level of nicotine? Can refractive index or polarimeter use to measure level of impurity?

    1 answer

    1. The measurement of purity in nicotine can be assessed using various analytical techniques. Refractive index and polarimetry are among the methods that can provide useful information. However, it's important to note that these techniques may not directly measure specific impurities but can be indicative of changes in the overall composition or characteristics of a substance. The purity of this product is determined by GC. Gas Chromatography (GC) is a widely used and effective method for assessing the purity of nicotine and detecting impurities. GC separates and analyzes components based on their volatility and interaction with a stationary phase.

      Please access a Certificate of Analysis in the DOCUMENTATION section for reference:
      https://www.sigmaaldrich.com/product/sigma/n3876#product-documentation

      Helpful?

  3. Hello, I would like to know the concentration of the nicotine in this liquid solution.

    1 answer

    1. This product is a neat or pure liquid. Based on the density of 1.02 g/mL and the molecular weight of 162.2 g/mole, the calculated molar concentration is 6.3 M.

      Helpful?

  4. How long is the nicotine stable if stored at room temperature? How long is it stable after being dssiolved and how should the solution be stored?

    1 answer

    1. This compound is stored at room temperature, but is extremely sensitive to light, moisture, and oxygen. The product is a neat liquid and packaged in amber glass under argon to preserve stability. In the unopened container, the product is stable at least until the recommended retest date reported on the lot specific Certificate of Analysis. This date is typically 3 years from the quality release date. Factors such as light, humidity, and exposure to air will limit the shelf life after opening, It is recommended to prepare solutions fresh. The vial head space should be cleared with argon or nitrogen prior to closing. Increased darkening of the material is an indication of product degradation. Please see the link below to review a sample Certificate of Analysis:
      https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/N3876-BULKBCCK8089.pdf

      Helpful?

  5. what % of ethanol should be used to be solublized?

    1 answer

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

      Helpful?

  6. Where should Product N3876, (-)-Nicotine, be stored and what sensitivities does it have?

    1 answer

    1. 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.

      Helpful?

  7. What is the difference between Nicotine, Products N3876 and N0267?

    1 answer

    1. Prod. No. N3876 is the naturally occurring (-) isomer while Prod. No. N0267 is a mixture of the (+) and (-) isomers.

      Helpful?

  8. What is the molarity of Product N3876,  (-)-Nicotine?

    1 answer

    1. 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.

      Helpful?

  9. What is the Department of Transportation shipping information for this product?

    1 answer

    1. 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.

      Helpful?

  10. How can Product N3876, (-)-Nicotine, be solublized?

    1 answer

    1. 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.

      Helpful?

1–10 of 11 Questions  

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service