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22620

Quinine

Name: Quinine
Brand: SIGMA

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

Synonym(s):

6′-Methoxycinchonidine

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₄N₂O₂

CAS Number:

130-95-0

Molecular Weight:

324.42

UNSPSC Code:

12171500

NACRES:

NA.32

PubChem Substance ID:

57647993

EC Number:

205-003-2

Beilstein/REAXYS Number:

91867

MDL number:

MFCD00198096

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Quality Level

100

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

fluorescence

λ_ex 347 nm; λ_em 448 nm in 0.5 M sulfuric acid

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

Gene Information

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

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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.
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.

Biochem/physiol Actions

Potassium channel blocker

pictograms

GHS07

signalword

Warning

hcodes

H302,H317

pcodes

P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

ppe

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

Regulatory Information

涉药品监管产品

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The role of friction in perceived oral texture.

Rene A. de Wijk , Jon F. Prinz.

Food Quality and Preference, 16, 121-129 (2005)

Microplate screening of the differential effects of test agents on Hoechst 33342, rhodamine 123, and rhodamine 6G accumulation in breast cancer cells that overexpress P-glycoprotein.

Jeffrey G Sarver et al.

Journal of biomolecular screening, 7(1), 29-34 (2002-03-19)

A microplate screening method has been developed to evaluate the effects of test agents on the accumulation of the fluorescent P-glycoprotein (Pgp) substrates Hoechst 33342, rhodamine 123, and rhodamine 6G in multidrug-resistant (MDR) breast cancer cells that overexpress Pgp. All

Antimalarial activity of Cinchona-like plants used to treat fever and malaria in Brazil.

V F Andrade-Neto et al.

Journal of ethnopharmacology, 87(2-3), 253-256 (2003-07-16)

For centuries, malaria was treated with the bark of Cinchona calisaya and Cinchona succirubra plants named "quinas" in Brazil, from which the quinine molecule was isolated. Other plant species known also as "quinas" are used to treat fever and malaria

The Journal of Organic Chemistry, 50, 1977-1977 (1985)

Catalytic site prediction and virtual screening of cytochrome P450 2D6 substrates by consideration of water and rescoring in automated docking.

Chris de Graaf et al.

Journal of medicinal chemistry, 49(8), 2417-2430 (2006-04-14)

Automated docking strategies successfully applied to binding mode predictions of ligands in Cyt P450 crystal structures in an earlier study (de Graaf et al. J. Med. Chem. 2005, 7, 2308-2318) were used for the catalytic site prediction (CSP) of 65

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Global Trade Item Number

SKU	GTIN
22620-25G	04061838780119
22620-100G	04061833379431
22620-5G	04061838780126

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