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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號碼:
205-003-2
MDL號碼:
MFCD00198096
分類程式碼代碼:
12171500
PubChem物質ID:
57647993
NACRES:
NA.32

化驗

≥98.0% (dried material, NT)

形狀

powder

光學活性

[α]20/D −126±5°, c = 1% in chloroform

雜質

≤5% dihydroquinine (HPLC)

損耗

≤1% loss on drying, 110 °C

mp

173-175 °C (lit.)

溶解度

H2O: soluble

螢光

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

適合性

suitable for fluorescence

SMILES 字串

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 密鑰

LOUPRKONTZGTKE-WZBLMQSHSA-N

基因資訊

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

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一般說明

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.

應用

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。

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險聲明

H302,H317

危險分類

Acute Tox. 4 Oral - Skin Sens. 1

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 1

個人防護裝備

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

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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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