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22620

Sigma-Aldrich

Quinine

suitable for fluorescence, anhydrous, ≥98.0% (dried material, NT)

Synonym(s):
6′-Methoxycinchonidine
Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
Molecular Weight:
324.42
Beilstein:
91867
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

assay

≥98.0% (dried material, NT)

form

powder

optical activity

[α]20/D −126±5°, c = 1% in chloroform

impurities

≤5% dihydroquinine (HPLC)

loss

≤1% loss on drying, 110 °C

mp

173-175 °C (lit.)

solubility

H2O: soluble

suitability

suitable for fluorescence

SMILES string

COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1

InChI

1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

InChI key

LOUPRKONTZGTKE-WZBLMQSHSA-N

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General description

Quinine, also known as 6′-Methoxycinchonidine is a fluorescent reagent. The quantum yield of Quinine is 23% higher at 390 mµ excitation wavelength than at 313 mµ. The fluorescence polarization in the emission band of quinine in a rigid medium arises from two singlet states simultaneously. The emission spectra of quinine or 6-methoxyquinoline shifts towards the red zone when excited at 390 mµ.

Application

Quinine was used in the following processes:

  • To study its in vitro antimalarial activity in combination with omeprazole.[1]
  • To analyze its effect on viscosity and friction of saliva.[2]
  • As a test agent to study its impact on the accumulation of the fluorescent P-glycoprotein (Pgp) substrates in P-glycoprotein overexpressing breast cancer cells.[3]
  • To study its influence on the pyramidal cell intrinsic properties, extracellular potassium transients, and epileptiform activity in vitro.[4]
  • As a reference compound to identify alkaloids by phytochemical screening of Deianira erubescens, Strychnos pseudoquina and Remijia ferruginea plants.[5]

Biochem/physiol Actions

Potassium channel blocker

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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