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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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Properties

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)

Description

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

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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)

A.A. Smaardijk et al.

The Journal of Organic Chemistry, 52, 135-135 (1987)

Dimeric Cinchona alkaloids.

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

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Global Trade Item Number

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