Skip to Content
Merck
All Photos(3)

Documents

C5923

Sigma-Aldrich

(−)-Cotinine

≥98% (TLC), crystals, nicotine metabolite

Synonym(s):

(S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone, S(−)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C10H12N2O
CAS Number:
486-56-6
Molecular Weight:
176.22
Beilstein:
83099
EC Number:
207-634-9
MDL number:
MFCD00077696
UNSPSC Code:
12352200
PubChem Substance ID:
24278324
NACRES:
NA.77

product name

(−)-Cotinine, ≥98%

Quality Level

200

Assay

≥98%

form

crystals

bp

250 °C/150 mmHg (lit.)

mp

40-42 °C (lit.)

storage temp.

2-8°C

SMILES string

CN1[C@@H](CCC1=O)c2cccnc2

InChI

1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1

InChI key

UIKROCXWUNQSPJ-VIFPVBQESA-N

Gene Information

human ... CYP1A2(1544) , CYP2A6(1548)
mouse ... Cyp2a5(13087)

Looking for similar products? Visit Product Comparison Guide

General description

Cotinine is an alkaloid extracted from tobacco leaves. It can cross the blood-brain barrier. Cotinine is used to treat Alzheimer′s disease (AD), schizophrenia and post-traumatic stress disorder (PTSD).

Application

Cotinine has been used:
  • for oxygen-glucose deprivation (OGD) studies to model ischemic stroke
  • as a standard to determine serum cotinine measurements using liquid chromatography with tandem mass spectrometry (LC-MS/MS)
  • to evaluate the adverse developmental potential of cotinine
  • to assess cognitive behavior in mice

Biochem/physiol Actions

Major metabolite of nicotine in humans.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

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

Visit the Document Library

Nicotine and electronic cigarette (E-Cig) exposure decreases brain glucose utilization in ischemic stroke
Sifat AE, et al.
Journal of Neurochemistry, 147(2), 204-221 (2018)
Evaluation of serum cotinine cut-off to distinguish smokers from nonsmokers in the Korean population
Ko K, et al.
Annals of Laboratory Medicine, 36(5), 427-433 (2016)
Cotinine administration improves impaired cognition in the mouse model of Fragile X syndrome
Pardo M, et al.
The European Journal of Neuroscience, 45(4), 490-498 (2017)
Cotinine: beyond that expected, more than a biomarker of tobacco consumption
Echeverria Moran V
Frontiers in Pharmacology, 3, 173-173 (2012)
Long-term cardiovascular reprogramming by short-term perinatal exposure to nicotine's main metabolite cotinine
Bastianini S, et al.
Acta Paediatrica (Oslo, Norway : 1992), 107(4), 638-646 (2018)
View All Related Papers

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