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Merck
CN
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安全信息

22620

Sigma-Aldrich

奎宁

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

别名:

6′-甲氧基辛可宁

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About This Item

经验公式（希尔记法）:
C20H24N2O2
CAS号:
130-95-0
分子量:
324.42
Beilstein:
91867
EC 号:
205-003-2
MDL编号:
MFCD00198096
UNSPSC代码:
12171500
PubChem化学物质编号:
57647993
NACRES:
NA.32

质量水平

100

方案

≥98.0% (dried material, NT)

表单

powder

旋光性

[α]20/D −126±5°, c = 1% in chloroform

杂质

≤5% dihydroquinine (HPLC)

缺失

≤1% loss on drying, 110 °C

mp

173-175 °C (lit.)

溶解性

H2O: soluble

荧光

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

适用性

suitable for fluorescence

SMILES字符串

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

基因信息

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

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一般描述

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.

应用

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.

生化/生理作用

钾通道阻断剂。

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H302,H317

危险分类

Acute Tox. 4 Oral - Skin Sens. 1

储存分类代码

11 - Combustible Solids

WGK

WGK 1

个人防护装备

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

法规信息

监管及禁止进口产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
BCCM6685
BCCL0830
BCCK4568
BCCJ1195
BCCF7206

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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
The role of friction in perceived oral texture.
Rene A. de Wijk , Jon F. Prinz.
Food Quality and Preference, 16, 121-129 (2005)
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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