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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
 

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
  • Muscarinic Antagonists
  • Neurotransmitter Agents
  • Skin / Eye Irritant
  • Sodium Channel Blockers
  • Voltage-Gated Sodium Channel Blockers

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
  • 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

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

InChIKey

LOUPRKONTZGTKE-LHHVKLHASA-N

Smiles

COc1ccc2nccc([C@H](O)[C@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1

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.