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Substance Name: Quinine [BAN:NF]
RN: 130-95-0
UNII: A7V27PHC7A
InChIKey: LOUPRKONTZGTKE-WZBLMQSHSA-N

Note

  • An alkaloid derived from the bark of the cinchona tree. It is used as an antimalarial drug, and is the active ingredient in extracts of the cinchona that have been used for that purpose since before 1633. Quinine is also a mild antipyretic and analgesic and has been used in common cold preparations for that purpose. It was used commonly and as a bitter and flavoring agent, and is still useful for the treatment of babesiosis. Quinine is also useful in some muscular disorders, especially nocturnal leg cramps and myotonia congenita, because of its direct effects on muscle membrane and sodium channels. The mechanisms of its antimalarial effects are not well understood.

Molecular Formula

  • C20-H24-N2-O2

Molecular Weight

  • 324.4216
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Central Nervous System Agents
  • Human Data
  • Muscle Relaxants, Central
  • Mutation Data
  • Neuromuscular Agents
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • 6'-Methoxycinchonan-9-ol
  • Cinchonan-9-ol, 6'-methoxy-
  • Quinine
  • Quinine [BAN:NF]

MeSH Heading

  • Quinine

Synonyms

  • (-)-Quinine
  • (8-alpha,9R)-6'-Methoxycinchonan-9-ol
  • (8S,9R)-Quinine
  • (R)-(-)-Quinine, 6-methoxycinchonidine
  • 2-Quinuclidinemethanol, alpha-(6-methoxy-4-quinolyl)-5-vinyl-
  • 6-Methoxycinchonine
  • CCRIS 5755
  • Chinin
  • Chinin [German]
  • Chinine
  • Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-
  • EC 205-003-2
  • EINECS 205-003-2
  • HSDB 2501
  • NSC 192949
  • NSC 5362
  • Quinine
  • Quinine anhydrous
  • UNII-A7V27PHC7A

Systematic Names

  • (8S,9R)-6'-Methoxycinchonan-9-ol
  • Cinchonan-9-ol, 6'-methoxy-, (8-alpha,9R)-
  • Cinchonan-9-ol, 6'-methoxy-, (8alpha,9R)-
  • Quinine

Superlist Name

  • Quinine

Registry Numbers

CAS Registry Number

  • 130-95-0

FDA UNII

  • A7V27PHC7A

Other Registry Numbers

  • 1071756-51-8
  • 12239-42-8
  • 128544-03-6
  • 21480-31-9
  • 55980-20-6
  • 6912-57-8
  • 72646-90-3
  • 767303-40-2
  • 840482-04-4
  • 857212-53-4
  • 864908-93-0
  • 875538-34-4
  • 888714-03-2
  • 890027-24-4
  • 894767-09-0
  • 898813-59-7
  • 898814-28-3
  • 899813-83-3
  • 900786-66-5
  • 900789-95-9
  • 906550-97-8
  • 909263-47-4
  • 909767-48-2
  • 909882-78-6
  • 910878-25-0
  • 910880-97-6
  • 911445-75-5
  • 918778-04-8
  • 95650-40-1

System Generated Number

  • 0000130950

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-WZBLMQSHSA-N

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 100mg/kg (100mg/kg)   Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
cat LDLo subcutaneous 100mg/kg (100mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
dog LDLo subcutaneous 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog LDLo intramuscular 400mg/kg (400mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog LDLo oral 1500mg/kg (1500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
frog LDLo subcutaneous 200mg/kg (200mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
guinea pig LD50 oral 1800mg/kg (1800mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 84, Pg. 351, 1954.
man LDLo unreported 294mg/kg (294mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LD50 intraperitoneal 115mg/kg (115mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 35, Pg. 1760, 1985.
mouse LD50 intravenous 68mg/kg (68mg/kg)   Japanese Journal of Toxicology. Vol. 4, Pg. 105, 1991.
mouse LDLo subcutaneous 200mg/kg (200mg/kg) CARDIAC: OTHER CHANGES

BLOOD: OTHER CHANGES

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
pigeon LDLo intramuscular 500mg/kg (500mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rabbit LDLo intravenous 70mg/kg (70mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rabbit LDLo oral 500mg/kg (500mg/kg)   Rivista di Malariologia. Vol. 11, Pg. 3, 1932.
rabbit LDLo subcutaneous 231mg/kg (231mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1320, 1935.
rat LD intraperitoneal > 100mg/kg (100mg/kg)   Cancer Research. Vol. 52, Pg. 2797, 1992.
rat LDLo oral 800mg/kg (800mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 100, Pg. 408, 1950.
rat LDLo subcutaneous 200mg/kg (200mg/kg) BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA

BLOOD: OTHER CHANGES

CARDIAC: OTHER CHANGES
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
women TDLo oral 74mg/kg (74mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: TINNITUS: EAR

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Ophthalmology. Vol. 90, Pg. 403, 1980.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 57 deg C   EXP
log P (octanol-water) 3.44 (none)   EXP
Water Solubility 500 mg/L 15 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.