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145904

Sigma-Aldrich

Quinine

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
Beilstein:
91867
EC Number:
205-003-2
MDL number:
MFCD00198096
UNSPSC Code:
12352104
PubChem Substance ID:
24848751
NACRES:
NA.22

Quality Level

200

Assay

90%

optical activity

[α]25/D −165°, c = 2 in ethanol

mp

173-175 °C (lit.)

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

Gene Information

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

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General description

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

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

Other Notes

remainder hydroquinine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)
Chirality, 4, 323-323 (1992)
Tetrahedron, 50, 4775-4775 (1994)
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
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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