| Identification | More | [Name]
Cinchonine | [CAS]
118-10-5 | [Synonyms]
4-QUINOLYL(5-VINYL-1-AZABICYCLO[2.2.2]OCT-2-YL)METHANOL
CINCHONAN-9-OL,(9S)-
(+)-CINCHONINE
CINCHONINE
D-CINCHONINE
(+)-cinconine
(8r,9s)-cinchonine
(9s)-cinchonan-9-o
(9S)-Cinchonan-9-ol
alpha-(5-vinyl-2-quinolyl)-2-quinuclidinemethano
alpha-4-quinolyl-5-vinyl-2-quinuclidinemethano
Cinchonine monohydrochloride dihydrate
CINCHONINE FREE BASE
CINCHONINE, CRYSTALLIZED
CINCHONINE PURE
CINCHONINE(P)
CINCHONINE(RG)
homocinchonidine
homoquinidine
Cinchonine (base and/or unspecified salts) | [EINECS(EC#)]
204-234-6 | [Molecular Formula]
C19H22N2O | [MDL Number]
MFCD00064372 | [Molecular Weight]
294.39 | [MOL File]
118-10-5.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
260-263 °C
| [alpha ]
224 º (c=0.5, alcohol) | [Boiling point ]
436.16°C (rough estimate) | [density ]
1.0863 (rough estimate) | [vapor pressure ]
0Pa at 25℃ | [refractive index ]
223 ° (C=0.5, EtOH) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
0.25g/l | [form ]
Micro-Crystalline Powder | [pka]
5.85, 9.92(at 25℃) | [color ]
White to light beige | [PH]
9.0 (0.25g/l, H2O, 20℃)(as aqueous solution) | [Stability:]
Stable, but may be light sensitive. Incompatible with strong oxidizing agents. | [optical activity]
[α]23/D +228°, c = 0.5 in ethanol | [Water Solubility ]
Insoluble | [Sensitive ]
Light Sensitive | [Merck ]
14,2287 | [BRN ]
89689 | [InChIKey]
KMPWYEUPVWOPIM-QHQSXHFQSA-N | [LogP]
2.82 at 25℃ | [CAS DataBase Reference]
118-10-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Cinchonine(118-10-5) | [EPA Substance Registry System]
118-10-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
1544 | [WGK Germany ]
3
| [RTECS ]
GD3500000
| [F ]
8-34 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29339900 | [Toxicity]
LD50 i.p. in rats: 152 mg/kg (Johnson, Poe) |
| Hazard Information | Back Directory | [Description]
Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions. It is a stereoisomer and pseudo-enantiomer of cinchonidine. It is structurally similar to quinine, an antimalarial drug. | [Chemical Properties]
white to light yellow crystal powde | [Uses]
cardiotonic | [Uses]
Cinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent. | [Uses]
Stereomeric with Cinchonidine (C441925). Antimalarial. | [Definition]
ChEBI: Cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis. | [Health Hazard]
The toxic effects from high doses of cinchonineinclude tinnitus, vomiting, diarrhea, andfever. The toxic effects noted in rats were excitement, change in motor activity, andconvulsions. An intraperitoneal LD50 valuein rats is 152 mg/kg. | [Flammability and Explosibility]
Nonflammable | [storage]
4°C, protect from light, stored under nitrogen | [Purification Methods]
Crystallise cinchonine from EtOH or diethyl ether. For the N-benzylcinchoninium chloride see above entry in this section. [Rabe Justus Liebigs Ann Chem 365 366, 371 1909, Beilstein 23 III/IV 2819, 2832.] |
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