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22620

Sigma-Aldrich

Quinine

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

Synonym(s):
6′-Methoxycinchonidine
Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
Molecular Weight:
324.42
Beilstein:
91867
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

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

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This Item
PHL8096222600145904
Quinine suitable for fluorescence, anhydrous, ≥98.0% (dried material, NT)

Sigma-Aldrich

22620

Quinine

(-)-Quinine phyproof® Reference Substance

PHL80962

(-)-Quinine

Quinidine crystallized, ≥98.0% (dried material, NT)

Sigma-Aldrich

22600

Quinidine

Quinine 90%

Sigma-Aldrich

145904

Quinine

form

powder

form

-

form

solid

form

-

optical activity

[α]20/D −126±5°, c = 1% in chloroform

optical activity

-

optical activity

[α]20/D +265±5°, c = 0.8% in ethanol (dry matter)

optical activity

[α]25/D −165°, c = 2 in ethanol

mp

173-175 °C (lit.)

mp

173-175 °C (lit.)

mp

168-172 °C (lit.)

mp

173-175 °C (lit.)

impurities

≤5% dihydroquinine (HPLC)

impurities

-

impurities

≤2% water, ~10% hydroquinidine (HPLC)

impurities

-

loss

≤1% loss on drying, 110 °C

loss

-

loss

-

loss

-

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

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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