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Substance Name: Cinchonine
RN: 118-10-5
UNII: V43X79NZCD
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N

Note

  • Diastereoisomer of cinchonidine with distinct physiochemical properties; occurs in most varieties of cinchona bark.

Molecular Formula

  • C19-H22-N2-O

Molecular Weight

  • 294.3958
 

Classification Codes

  • Anti-Infective Agents
  • Antimalarials
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Cinchonine

Synonyms

  • (+)-Cinconine
  • (8R,9S)-Cinchonine
  • (9S)-Cinchonan-9-ol
  • 2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-
  • 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl-
  • AI3-09058
  • Cinchonine
  • d-Cinchonine
  • EINECS 204-234-6
  • NSC 6176
  • UNII-V43X79NZCD

Systematic Names

  • alpha-(5-Vinyl-2-quinuclidinyl)-4-quinolinemethanol
  • Cinchonan-9-ol, (9S)-
  • Cinchonine

Registry Numbers

CAS Registry Number

  • 118-10-5

FDA UNII

  • V43X79NZCD

Other Registry Numbers

  • 1236363-47-5
  • 185122-83-2
  • 201406-15-7
  • 24831-03-6
  • 887770-70-9
  • 896440-46-3
  • 898337-50-3
  • 898814-05-6
  • 900786-85-8
  • 909881-46-5
  • 910892-13-6

System Generated Number

  • 0000118105

Structure Descriptors

InChI

1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1

InChIKey

KMPWYEUPVWOPIM-QAMTZSDWSA-N

Smiles

O[C@H]([C@H]1C[C@@H]2CCN1C[C@@H]2C=C)c3ccnc4ccccc34

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
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.
mouse LDLo subcutaneous 400mg/kg (400mg/kg) CARDIAC: OTHER CHANGES

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 205, Pg. 129, 1948.
rat LD50 intraperitoneal 152mg/kg (152mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: EXCITEMENT
Acta Pharmacologica et Toxicologica. Vol. 4, Pg. 265, 1948.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 265 deg C   EXP
log P (octanol-water) 2.68 (none)   EXP
Water Solubility 240 mg/L   EXP
Vapor Pressure 9.04E-10 mm Hg 25 EST
Henry's Law Constant 1.45E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.33E-10 cm3/molecule-sec 25 EST

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