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22620

Sigma-Aldrich

Quinine

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

Sinónimos:

6′-Methoxycinchonidine

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About This Item

Fórmula empírica (notación de Hill):
C20H24N2O2
Número de CAS:
130-95-0
Peso molecular:
324.42
Beilstein:
91867
Número CE:
205-003-2
Número MDL:
MFCD00198096
Código UNSPSC:
12171500
ID de la sustancia en PubChem:
57647993
NACRES:
NA.32

Nivel de calidad

100

Ensayo

≥98.0% (dried material, NT)

Formulario

powder

actividad óptica

[α]20/D −126±5°, c = 1% in chloroform

impurezas

≤5% dihydroquinine (HPLC)

pérdida

≤1% loss on drying, 110 °C

mp

173-175 °C (lit.)

solubilidad

H2O: soluble

fluorescencia

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

idoneidad

suitable for fluorescence

cadena 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

Clave InChI

LOUPRKONTZGTKE-WZBLMQSHSA-N

Información sobre el gen

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

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Descripción general

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.

Aplicación

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.

Acciones bioquímicas o fisiológicas

Potassium channel blocker

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302,H317

Clasificaciones de peligro

Acute Tox. 4 Oral - Skin Sens. 1

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 1

Equipo de protección personal

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

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Certificados de análisis (COA)

Lot/Batch Number
BCCF7206
BCCD7819
BCCC9175
BCCB3513
BCBX3884

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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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