Cinchonine
Synonym(s):(+)-Cinchonine;Cinchonine;Cinchonine monohydrochloride dihydrate;NSC 6176
- CAS NO.:118-10-5
- Empirical Formula: C19H22N2O
- Molecular Weight: 294.39
- MDL number: MFCD00064372
- EINECS: 204-234-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-12-18 13:37:16
What is Cinchonine?
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
The Uses of Cinchonine
Cinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent.
The Uses of Cinchonine
cardiotonic
The Uses of Cinchonine
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
Non flammable
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.]
Properties of Cinchonine
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) |
optical activity | [α]23/D +228°, c = 0.5 in ethanol |
Water Solubility | Insoluble |
Sensitive | Light Sensitive |
Merck | 14,2287 |
BRN | 89689 |
Stability: | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
CAS DataBase Reference | 118-10-5(CAS DataBase Reference) |
NIST Chemistry Reference | Cinchonine(118-10-5) |
EPA Substance Registry System | Cinchonan-9-ol, (9S)- (118-10-5) |
Safety information for Cinchonine
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H317:Sensitisation, Skin |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. |
Computed Descriptors for Cinchonine
InChIKey | KMPWYEUPVWOPIM-QHQSXHFQSA-N |
Cinchonine manufacturer
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