Cinchonidine
Cinchonidine
CAS: 485-71-2
Molecular Formula: C19H22N2O
Cinchonidine - Names and Identifiers
| Name | Cinchonidine |
| Synonyms | Cinchonidine Cinchovatine L-Cinchonidine Cinchonan-9-ol alpha-Quinidine (9R)-cinchonan-9-ol (8s,9r)-cinchonidine (9R)-cinchonan-1-ium-9-ol (8alpha,9R)-Cinchonan-9-ol (8-alpha,9r)-cinchonan-9-o Cinchonidinederivedcatalyst Cinchonan-9-ol, (8alpha,9R)- (8alpha,9theta)-cinchonan-9-o (8alpha,9R)-9-hydroxycinchonan-1-ium (3alpha,9R)-9-hydroxycinchonan-1-ium (4beta,8alpha,9R)-cinchonan-1-ium-9-ol (3alpha,4beta,8alpha,9S)-cinchonan-9-ol 2-Quinuclidinemethanol, alpha-4-quinolyl-5-vinyl- |
| CAS | 485-71-2 |
| EINECS | 207-622-3 |
| InChI | InChI=1/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/p+1/t13-,14+,18-,19-/m1/s1 |
| InChIKey | KMPWYEUPVWOPIM-NAHPKXJFSA-N |
Cinchonidine - Physico-chemical Properties
| Molecular Formula | C19H22N2O |
| Molar Mass | 294.39 |
| Density | 1.0863 (rough estimate) |
| Melting Point | 204-206°C(lit.) |
| Boling Point | 436.16°C (rough estimate) |
| Specific Rotation(α) | -115 º (c=1, EtOH) |
| Flash Point | 234.723°C |
| Water Solubility | Insoluble |
| Solubility | 0.25g/l |
| Vapor Presure | 0Pa at 25℃ |
| Appearance | Bright yellow crystal |
| Color | White to cream |
| Merck | 14,2286 |
| BRN | 89690 |
| pKa | 5.80, 10.03(at 25℃) |
| PH | 9 (0.2g/l, H2O, 20℃) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Stable, but light-sensitive. Incompatible with strong oxidizing agents. |
| Sensitive | Light Sensitive |
| Refractive Index | -107.5 ° (C=1, EtOH) |
| MDL | MFCD00006783 |
| In vitro study | Cinchonidine (α-Quinidine) is a cinchona alkaloid found in Cinchona officinalis and Gongronema latifolium. A building block used in asymmetric synthesis in organic chemistry. Weak inhibitor of serotonin transporter (SERT) with K i s of 330, 4.2, 36, 196, 15 μM for dSERT, hSERT, hSERT I172M, hSERT S438T, hSERT Y95F, respectively. |
Cinchonidine - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R42/43 - May cause sensitization by inhalation and skin contact. R36/37/38 - Irritating to eyes, respiratory system and skin. R20/22 - Harmful by inhalation and if swallowed. R48/22 - Harmful danger of serious damage to health by prolonged exposure if swallowed. R43 - May cause sensitization by skin contact R22 - Harmful if swallowed R63 - Possible risk of harm to the unborn child |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36/37 - Wear suitable protective clothing and gloves. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 1544 |
| WGK Germany | 3 |
| RTECS | GD2975000 |
| TSCA | Yes |
| HS Code | 29392900 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 i.p. in rats: 206 mg/kg (Johnson, Poe); LD50 orally in quail: >316 mg/kg (Schafer) |
Cinchonidine - Introduction
Insoluble in water, soluble in alcohol and chloroform.
Last Update：2022-10-16 17:25:24
Cinchonidine - Reference Information
| LogP | 2.68 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Introduction | Cinconidine is a quinoline alkaloid, a kind of cinchona alkaloid, also known as cinchona nidin, which is the stereoisomer of cinchonine. White needle-like or prismatic crystals obtained from ether. Melting point 204~206 ℃, specific rotation -115 (ethanol, C = 1), refractive index -107.5 (ethanol, C = 1). Soluble in alcohol, ether, acetone, benzene and chloroform, almost insoluble in cold water. |
| application | cinkonidine is an organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory organic synthesis process and chemical medicine research and development process. |
| Effect | Like quinine, it has antimalarial effect. After quinine can be separated from cinchona bark extract, the mother liquor is treated with alkali to precipitate alkaloids, and tartaric acid is added to make it insoluble tartrate separated. |
| Structural characteristics | Cinchona (such as quinine, quinidine, cinkonine, cinkonidine, etc.) is a kind of natural product of great significance found in cinchona bark about two centuries ago. In the early years, it was a specific drug for the treatment of malaria. In recent years, it has been used as the dominant framework of catalysts in asymmetric synthesis. From the perspective of biosynthesis, cinchona alkaloids are derived from monoterpene indole alkaloids. |
| Biological activity | Cinchonidine is an alkaloid used in asymmetric synthesis in organic chemistry. |
| target | ki: 330 μ m (dSERT), 4.2 μ m (hSERT), 36 μ m (hSERT i172m), 196 μ m (hSERT s438t), 15 μ m (hSERT y95f) |
Last Update：2024-04-09 20:52:54
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View History
Cinchonidine
3-Amino-2-phenylimidazo(1,2-a)pyridine
Formic acid, azodi-, diethyl ester
Ethanol, 2-ethoxy-
339-17-3
DIPHENYLTHIOMETHANE
1-amino-2-[2-(2-methoxyethoxy)ethoxy]-4-(2,4,6-trimethylanilino)anthracene-9,10-dione
methylbensulfuron
4,4-Dimethoxy-4-silavaleronitrile
Benzenamine, N,4-dihexyl-
3-Amino-2-phenylimidazo(1,2-a)pyridine
Formic acid, azodi-, diethyl ester
Ethanol, 2-ethoxy-
339-17-3
DIPHENYLTHIOMETHANE
1-amino-2-[2-(2-methoxyethoxy)ethoxy]-4-(2,4,6-trimethylanilino)anthracene-9,10-dione
methylbensulfuron
4,4-Dimethoxy-4-silavaleronitrile
Benzenamine, N,4-dihexyl-