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Merck
CN

22620

奎宁

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

别名:

6′-甲氧基辛可宁

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经验公式（希尔记法）:
C20H24N2O2
化学文摘社编号:
130-95-0
分子量:
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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产品名称

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

InChI key

LOUPRKONTZGTKE-WZBLMQSHSA-N

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

SMILES string

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

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

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

suitability

suitable for fluorescence

Quality Level

100

Gene Information

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

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Biochem/physiol Actions

钾通道阻断剂。

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.

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.

wgk

WGK 1

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

存储类别

11 - Combustible Solids

ppe

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

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCCN9535
BCCM6685
BCCL0830
BCCK4568
BCCJ1195

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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)
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
Some characteristics of the fluorescence of quinine.
R F Chen
Analytical biochemistry, 19(2), 374-387 (1967-05-01)
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
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