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Substance Name: Quinidine [BAN:NF]
RN: 56-54-2
UNII: ITX08688JL
InChIKey: LOUPRKONTZGTKE-LHHVKLHASA-N
Note
- An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.
Molecular Formula
- C20-H24-N2-O2
Molecular Weight
- 324.4216
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
- Adrenergic Agents
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Anti-Arrhythmia Agents
- Anti-Infective Agents
- Antimalarials
- Antiparasitic Agents
- Antiprotozoal Agents
- Cardiovascular Agents
- Cholinergic Agents
- Cholinergic Antagonists
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 Enzyme Inhibitors
- Drug / Therapeutic Agent
- Enzyme Inhibitors
- Membrane Transport Modulators
- Metabolic Side Effects of Drugs and Substances
- Muscarinic Antagonists
- Neurotransmitter Agents
- Skin / Eye Irritant
- Sodium Channel Blockers
- Voltage-Gated Sodium Channel Blockers
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Names and Synonyms
Name of Substance
- Quinidine
- Quinidine [BAN:NF]
MeSH Heading
- Quinidine
Synonyms
- (+)-Quinidine
- (8R,9S)-Quinidine
- (9S)-6'-Methoxycinchonan-9-ol
- (9S)-6-Methoxy-alpha-(5-vinyl-2-quinuclidinyl)-4-quinolinemethanol
- alpha-(6-Methoxy-4-quinolyl)-5-vinyl-2-quinuclidinemethanol (9S)-
- beta-Quinidine
- beta-Quinine
- CCRIS 672
- Chinidin
- Chinidin [German]
- Cinchonan-9-ol, 6'-methoxy-, (9S)-
- Conchinin
- Conquinine
- EINECS 200-279-0
- HSDB 225
- NCI-C56246
- Pitayine
- Quinidex
- Quinidine
- UNII-ITX08688JL
Systematic Names
- (8R,9S)-6'-Methoxycinchonan-9-ol
- Cinchonan-9-ol, 6'-methoxy-, (9S)-
- Quinidine
Registry Numbers
CAS Registry Number
- 56-54-2
FDA UNII
- ITX08688JL
Other Registry Numbers
- 11010-73-4
- 1528764-92-2
- 2393956-08-4
- 500225-45-6
- 845886-64-8
- 882741-47-1
- 883881-01-4
- 898814-00-1
- 910899-51-3
System Generated Number
- 0000056542
Structure Descriptors
InChI
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/s1InChIKey
LOUPRKONTZGTKE-LHHVKLHASA-NSmiles
COc1ccc2nccc([C@H](O)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
cat | LD50 | intravenous | 30mg/kg (30mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 226, Pg. 286, 1977. | |
mammal (species unspecified) | LD50 | unreported | 67mg/kg (67mg/kg) | Farmakologiya i Toksikologiya Vol. 48(5), Pg. 43, 1985. | |
mouse | LD50 | intramuscular | 200mg/kg (200mg/kg) | "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 232, 1973. | |
mouse | LD50 | intraperitoneal | 135mg/kg (135mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 137, Pg. 410, 1962. | |
mouse | LD50 | intravenous | 53600ug/kg (53.6mg/kg) | Journal of Medicinal Chemistry. Vol. 27, Pg. 1142, 1984. | |
mouse | LD50 | oral | 535mg/kg (535mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 105, Pg. 291, 1952. | |
mouse | LDLo | subcutaneous | 400mg/kg (400mg/kg) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948. | |
rat | LD50 | intravenous | 23mg/kg (23mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 22, 1960. | |
rat | LD50 | oral | 263mg/kg (263mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 589, 1977. | |
rat | LD50 | unreported | 60mg/kg (60mg/kg) | Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 174 | deg C | EXP | |
pKa Dissociation Constant | 8.56 | (none) | 25 | EXP |
log P (octanol-water) | 3.44 | (none) | EXP | |
Water Solubility | 140 | mg/L | 25 | EXP |
Vapor Pressure | 1.10E-10 | mm Hg | 25 | EST |
Henry's Law Constant | 8.58E-16 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.75E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.