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Substance Name: Quinidine sulfate anhydrous
RN: 50-54-4
UNII: 140CU2322K
InChIKey: RONWGALEIBILOG-VCSAERELSA-N

Note

  • An optical isomer of quinine, extracted from the bark of the Cinchona 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 potential, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.

Molecular Formula

  • C20-H24-N2-O2.1/2H2-O4-S

Molecular Weight

  • 746.921
 

Classification Codes

  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Quinidine sulfate
  • Quinidine sulfate anhydrous

Synonyms

  • (9S)-6'-Methoxycinchonan-9-ol sulfate (2:1) (salt)
  • Auriquin
  • Chinidine sulfate
  • Cin-Quin
  • Cinchonan-9-ol, 6'-methoxy-, (9S)-, sulfate (2:1) (salt)
  • EINECS 200-046-3
  • HSDB 5515
  • Kinichron
  • NSC 10004
  • Quinicardine
  • Quinidate
  • Quinidex
  • Quinidine monosulfate
  • Quinidine sulfate
  • Quinidine sulfate (salt)
  • Quinidine sulfate, (2:1) (salt)
  • Quinidine sulphate
  • Quinitex
  • Quinora
  • sk-Quinidine sulfate
  • Systodin
  • UNII-140CU2322K

Systematic Names

  • Cinchonan-9-ol, 6'-methoxy-, (9S)-, sulfate (2:1)
  • Cinchonan-9-ol, 6'-methoxy-, (9S)-, sulfate (2:1) (salt)
  • Quinidine sulfate (2:1) (salt)
  • Quinidine sulphate

Registry Numbers

CAS Registry Number

  • 50-54-4

FDA UNII

  • 140CU2322K

Other Registry Numbers

  • 11034-22-3
  • 30356-06-0
  • 804-62-6

System Generated Number

  • 0000050544

Molecular Formulas

Molecular Formula

  • C20-H24-N2-O2.1/2H2-O4-S

Molecular Formula Fragments

  • C20-H24-N2-O2
  • COMPONENT
  • H2-O4-S

Structure Descriptors

InChI

1S/2C20H24N2O2.H2O4S/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;1-5(2,3)4/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H2,1,2,3,4)/t2*13-,14-,19+,20-;/m00./s1

InChIKey

RONWGALEIBILOG-VCSAERELSA-N

Smiles

COc1ccc2c(c1)c(ccn2)[C@@H]([C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O.COc1ccc2c(c1)c(ccn2)[C@@H]([C@H]3C[C@@H]4CC[N@]3C[C@@H]4C=C)O.OS(=O)(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 16mg/kg (16mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 833, 1980.
dog LDLo intravenous 19mg/kg (19mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drugs under Experimental and Clinical Research. Vol. 10, Pg. 197, 1984.
guinea pig LD50 oral 362mg/kg (362mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
guinea pig LDLo intravenous 117mg/kg (117mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
human TDLo oral 9600mg/kg/8W (9600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: TREMOR
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 884, 1977.
man LDLo multiple routes 30mg/kg/2D-I (30mg/kg) LUNGS, THORAX, OR RESPIRATION: CYANOSIS

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)
Annals of Internal Medicine. Vol. 16, Pg. 571, 1942.
man TDLo oral 88mg/kg/10D-I (88mg/kg)   Gastroenterology. Vol. 70, Pg. 1136, 1976.
man TDLo oral 88mg/kg/10D-I (88mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" Gastroenterology. Vol. 70, Pg. 1136, 1976.
man TDLo oral 240mg/kg/2W-I (240mg/kg) ENDOCRINE: TUMORS

MUSCULOSKELETAL: JOINTS

SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE
Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 367, 1983.
man TDLo oral 386mg/kg/30D- (386mg/kg)   American Journal of Medicine. Vol. 77, Pg. 345, 1984.
man TDLo oral 386mg/kg/30D- (386mg/kg) BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) American Journal of Medicine. Vol. 77, Pg. 345, 1984.
mouse LD50 intraperitoneal 135mg/kg (135mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 124, Pg. 53, 1958.
mouse LD50 intravenous 54mg/kg (54mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 105, Pg. 221, 1956.
mouse LD50 oral 505mg/kg (505mg/kg)   Farmaco, Edizione Pratica. Vol. 35, Pg. 49, 1980.
rabbit LD50 intravenous 30mg/kg (30mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 32, Pg. 833, 1980.
rat LD50 intravenous 55mg/kg (55mg/kg)   Polish Journal of Pharmacology and Pharmacy. Vol. 44, Pg. 187, 1992.
rat LD50 oral 456mg/kg (456mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1127, 1968.
rat LD50 subcutaneous 610mg/kg (610mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 18, Pg. 1127, 1968.
rat LDLo intraperitoneal 140mg/kg (140mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women TDLo oral 32mg/kg/2D (32mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, IRRITATIVE: AFTER SYSTEMIC EXPOSURE" Drug Intelligence and Clinical Pharmacy. Vol. 16, Pg. 615, 1982.
women TDLo oral 272mg/kg/17D- (272mg/kg) VASCULAR: OTHER CHANGES Archives of Internal Medicine. Vol. 145, Pg. 2051, 1985.
women TDLo oral 409gm/kg/14Y (409000mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" JAMA, Journal of the American Medical Association. Vol. 237, Pg. 2093, 1977.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 4.2 (none)   EXP
log P (octanol-water) 5.400 (none)   EST
Water Solubility 1.05E+04 mg/L 25 EXP
Vapor Pressure 3.55E-28 mm Hg 25 EST
Atmospheric OH Rate Constant 3.70E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.