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Q3625

Sigma-Aldrich

Quinidine

anhydrous

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
56-54-2
Molecular Weight:
324.42
Beilstein/REAXYS Number:
91866
EC Number:
200-279-0
MDL number:
MFCD00135581
UNSPSC Code:
12352200
PubChem Substance ID:
24899331
NACRES:
NA.77

grade

anhydrous

Quality Level

200

impurities

≤20% Dihydroquinidine (according to USP specifications., actual content given on label)

mp

168-172 °C (lit.)

originator

Bayer

SMILES string

COc1ccc2nccc([C@H](O)C3CC4CCN3C[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-LHHVKLHASA-N

Gene Information

human ... ABCB1(5243) , CYP2D6(1565) , CYP3A4(1576) , KCNH1(3756) , SCN10A(6336) , SCN11A(11280) , SCN1A(6323) , SCN2A(6326) , SCN3A(6328) , SCN4A(6329) , SCN5A(6331) , SCN7A(6332) , SCN8A(6334) , SCN9A(6335)
mouse ... Abcb1a(18671) , Abcb1b(18669)
rat ... Cyp2d1(266684) , Cyp2d2(25053) , Cyp2d3(24303) , Cyp2d4v1(171522)

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Application

Quinidine has been used:
  • as an inhibitor of cytochrome P450 enzyme isoform CYP2D6
  • as a potassium (K+) channel blocker in microglia
  • to test its effect on electrophysiological behaviour of human induced pluripotent stem cells (hiPSC) cardiomyocytes

Biochem/physiol Actions

Quinidine, an isomer of quinine has potential side effects like proarrhythmia on usage. It prolongs cardiac potential and is sodium channel blocker. It is a potential antagonist for α1-adrenoceptors and contributes to hypotension. It inhibits cytochrome P450 2D6 and improves circulation and brain penetration of dementia drug, dextromethorphan. Quinidine-dextromethorphan combination may be useful in treating pseudobulbar affect (PBA).
Class IA antiarrhythmic; potassium channel blocker.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Bayer. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Skin Sens. 1

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Quinidine sulfate European Pharmacopoeia (EP) Reference Standard

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Sigma-Aldrich

337714

Hydroquinine

Danny Jans et al.
Journal of pharmacological and toxicological methods, 87, 48-52 (2017-05-28)
Drug-induced cardiotoxicity poses a negative impact on public health and drug development. Cardiac safety pharmacology issues urged for the preclinical assessment of drug-induced ventricular arrhythmia leading to the design of several in vitro electrophysiological screening assays. In general, patch clamp
Pharmacological treatments for alleviating agitation in dementia: a systematic review and network meta-analysis
Kongpakwattana K, et al.
British Journal of Clinical Pharmacology, 84(7), 1445-1456 (2018)
Pharmacological evaluation of C-3 modified Betulinic acid derivatives with potent anticancer activity
Rajendran P, et al.
Investigational New Drugs, 26(1), 25-34 (2008)
Effects of quinidine and verapamil on human cardiovascular alpha1-adrenoceptors
Shibata K, et al.
Circulation, 97(13), 1227-1230 (1998)
Cardiac Sodium Channel Disorders An Issue of Cardiac Electrophysiology Clinics E-Book, 6(4) (2015)
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LC/MS/MS Analysis of Interacting Cardiac Drugs Digoxin, Quinidine, Amiodarone and Verapamil on Titan™ C18

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