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C5923

(−)-Cotinine

Name: (&#8722;)-Cotinine
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24278324

UNSPSC Code:

12352200

EC Number:

207-634-9

MDL number:

MFCD00077696

Beilstein/REAXYS Number:

83099

Assay:

≥98%

Form:

crystals

Quality level:

200

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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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

GHS07

signalword

Warning

hcodes

H302,H315,H319,H335

pcodes

P261 - P264 - P270 - P301 + P312 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number

0000526937

0000486017

0000505083

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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)

Cotinine: beyond that expected, more than a biomarker of tobacco consumption

Echeverria Moran V

Frontiers in Pharmacology, 3, 173-173 (2012)

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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Global Trade Item Number

SKU	GTIN
C5923-1G	04061833502679
C5923-250MG	04061833502686

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