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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

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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)

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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’.

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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)
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)
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