Quinine

Name: Quinine
Brand: ALDRICH

90%

Synonym(s):

6′-Methoxycinchonidine

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₄N₂O₂

CAS Number:

130-95-0

Molecular Weight:

324.42

UNSPSC Code:

12352104

NACRES:

NA.22

PubChem Substance ID:

24848751

EC Number:

205-003-2

Beilstein/REAXYS Number:

91867

MDL number:

MFCD00198096

Product Name

Quinine, 90%

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

90%

optical activity

[α]25/D −165°, c = 2 in ethanol

mp

173-175 °C (lit.)

functional group

hydroxyl

Quality Level

200

Gene Information

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

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Catalysts

Chiral Catalysts & Ligands

Application

Quinine has been used as a standard during the chemical evaluation of alkaloids in the hydroethanolic extracts of endophytic fungi obtained from the leaves of Costus spiralis by TLC.

Resolving agent for carboxylic acids. Catalyzes the kinetic resolution of furanones.

Biochem/physiol Actions

Potassium channel blocker

General description

Quinine, a cinchona alkaloid found in the bark of the cinchona tree, is known for its anti-malarial property.

Other Notes

remainder hydroquinine

pictograms

GHS07

signalword

Warning

hcodes

H302,H317

pcodes

P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

ppe

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

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Chemical assessment and antimicrobial and antioxidant activities of endophytic fungi extracts isolated from Costus spiralis (Jacq.) Roscoe (Costaceae)

Marson Ascencio PG, et al

Evidence-Based Complementary and Alternative Medicine : ECAM, 2014 (2014)

Tetrahedron, 50, 4775-4775 (1994)

Chirality, 4, 323-323 (1992)

In vitro antimalarial activity of azithromycin, artesunate, and quinine in combination and correlation with clinical outcome.

Harald Noedl et al.

Antimicrobial agents and chemotherapy, 51(2), 651-656 (2006-11-23)

Azithromycin when used in combination with faster-acting antimalarials has proven efficacious in treating Plasmodium falciparum malaria in phase 2 clinical trials. The aim of this study was to establish optimal combination ratios for azithromycin in combination with either dihydroartemisinin or

Catalytic site prediction and virtual screening of cytochrome P450 2D6 substrates by consideration of water and rescoring in automated docking.

Chris de Graaf et al.

Journal of medicinal chemistry, 49(8), 2417-2430 (2006-04-14)

Automated docking strategies successfully applied to binding mode predictions of ligands in Cyt P450 crystal structures in an earlier study (de Graaf et al. J. Med. Chem. 2005, 7, 2308-2318) were used for the catalytic site prediction (CSP) of 65

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