Q3625

Quinidine

sodium channel blocker

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

Properties

• Product Name: Quinidine, anhydrous
• 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)

Description

Application

Quinidine has been used:

• as an inhibitor of cytochrome P450 enzyme isoform CYP2D6[1]
• as a potassium (K⁺) channel blocker in microglia[2]
• to test its effect on electrophysiological behaviour of human induced pluripotent stem cells (hiPSC) cardiomyocytes[3]

Biochem/physiol Actions

Class IA antiarrhythmic; potassium channel blocker.

Quinidine, an isomer of quinine has potential side effects like proarrhythmia on usage. It prolongs cardiac potential and is sodium channel blocker.[4] It is a potential antagonist for α1-adrenoceptors and contributes to hypotension.[5] It inhibits cytochrome P450 2D6 and improves circulation and brain penetration of dementia drug, dextromethorphan.[6] Quinidine-dextromethorphan combination may be useful in treating pseudobulbar affect (PBA).[7]

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.

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301,H317
• Precautionary Statements: P261 - P264 - P272 - P280 - P301 + P310 - P302 + P352
• Hazard Classifications: Acute Tox. 3 Oral - Skin Sens. 1
• Storage Class Code: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 1
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves