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22620

Sigma-Aldrich

Quinine

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

Synonyme(s) :

6′-Methoxycinchonidine

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About This Item

Formule empirique (notation de Hill):
C20H24N2O2
Numéro CAS:
130-95-0
Poids moléculaire :
324.42
Numéro Beilstein :
91867
Numéro CE :
205-003-2
Numéro MDL:
MFCD00198096
Code UNSPSC :
12171500
ID de substance PubChem :
57647993
Nomenclature NACRES :
NA.32

Pureté

≥98.0% (dried material, NT)

Forme

powder

Activité optique

[α]20/D −126±5°, c = 1% in chloroform

Impuretés

≤5% dihydroquinine (HPLC)

Perte

≤1% loss on drying, 110 °C

Pf

173-175 °C (lit.)

Solubilité

H2O: soluble

Fluorescence

λex 347 nm; λem 448 nm in 0.5 M sulfuric acid

Adéquation

suitable for fluorescence

Chaîne SMILES 

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

Clé InChI

LOUPRKONTZGTKE-WZBLMQSHSA-N

Informations sur le gène

human ... ABCB1(5243) , CYP2C9(1559) , CYP2D6(1565)
rat ... Cyp2d1(266684) , Cyp2d2(25053) , Cyp2d3(24303) , Cyp2d4v1(171522)

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Description générale

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.
  • To analyze its effect on viscosity and friction of saliva.
  • 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.
  • To study its influence on the pyramidal cell intrinsic properties, extracellular potassium transients, and epileptiform activity in vitro.
  • As a reference compound to identify alkaloids by phytochemical screening of Deianira erubescens, Strychnos pseudoquina and Remijia ferruginea plants.

Actions biochimiques/physiologiques

Potassium channel blocker

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302,H317

Classification des risques

Acute Tox. 4 Oral - Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificats d'analyse (COA)

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Przemysław J Boratyński
Molecular diversity, 19(2), 385-422 (2015-01-15)
Nature is full of dimeric alkaloids of various types from many plant families, some of them with interesting biological properties. However, dimeric Cinchona alkaloids were not isolated from any species but were products of designed partial chemical synthesis. Although the
A.A. Smaardijk et al.
The Journal of Organic Chemistry, 52, 135-135 (1987)
The role of friction in perceived oral texture.
Rene A. de Wijk , Jon F. Prinz.
Food Quality and Preference, 16, 121-129 (2005)
T Skinner-Adams et al.
Antimicrobial agents and chemotherapy, 43(5), 1304-1306 (1999-05-01)
Previous studies have shown that the proton pump inhibitor omeprazole has antimalarial activity in vitro. The interactions of omeprazole with commonly used antimalarial drugs were assessed in vitro. Omeprazole and quinine combinations were synergistic; however, chloroquine and omeprazole combinations were
M Bikson et al.
Neuroscience, 115(1), 251-261 (2002-10-29)
The effect of quinine on pyramidal cell intrinsic properties, extracellular potassium transients, and epileptiform activity was studied in vitro using the rat hippocampal slice preparation. Quinine enhanced excitatory post-synaptic potentials and decreased fast- and slow-inhibitory post-synaptic potentials. Quinine reduced the
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