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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)

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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Biochem/physiol Actions

Potassium channel blocker

Other Notes

Chiral catalyst, used e.g. in highly enantioselective [2+2] cycloadditions; In additions of diethylzinc to aldehydes.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

The role of friction in perceived oral texture.
Rene A. de Wijk , Jon F. Prinz.
Food Quality and Preference, 16, 121-129 (2005)
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...
The Journal of Organic Chemistry, 50, 1977-1977 (1985)

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