Name | Quinine |
Synonyms | Quinine Quinine free base Quinine anhydrous (8R,9S)-Quinidine-d3 6'-methoxycinchonan-9-ol (9S)-6'-Methoxycinchonan-9-ol-d3 Quinine Anhydrous, for Fluorescene (4beta,9R)-6'-methoxycinchonan-9-ol (8alpha,9R)-6'-methoxycinchonan-9-ol (-)-QUININE FOR RESOLUTION OF RACEMATES (3alpha,4beta,9S)-6'-methoxycinchonan-9-ol (3alpha,9S)-6'-methoxycinchonan-1-ium-9-ol (9R)-6'-methoxycinchonan-9-ol sulfate (salt) (8alpha,9R)-9-hydroxy-6'-methoxycinchonan-1-ium (4beta,8alpha,9R)-6'-methoxycinchonan-1-ium-9-ol (1R)-(6-Methoxyquinolin-4-yl)(5-vinylquinuclidin-2-yl)Methanol (6-Methoxy-4-quinolyl)(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol (R)-(6-Methoxyquinolin-4-yl)((1R,2R,4R,5S)-5-vinylquinuclidin-2-yl)Methanol (R)-[(2S,4S,5R)-1-Aza-5-vinylbicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol Quinine, (R)-[(2S,4S,5R)-1-Aza-5-ethenylbicyclo[2.2.2]oct-2-yl](6-methoxyquinolin-4-yl)methanol |
CAS | 130-95-0 |
EINECS | 205-003-2 |
InChI | InChI=1/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/p+1/t13-,14-,19-,20+/m0/s1 |
Molecular Formula | C20H24N2O2 |
Molar Mass | 324.42 |
Density | 1.1294 (rough estimate) |
Melting Point | 173-175°C(lit.) |
Boling Point | 462.75°C (rough estimate) |
Specific Rotation(α) | -172 º (c=1, EtOH) |
Flash Point | >110°C (>230°F) |
Water Solubility | slightly soluble |
Solubility | Soluble in ethanol, chloroform and ether. Slightly soluble in water and glycerin. |
Vapor Presure | 0Pa at 25℃ |
Appearance | White powder |
Color | White |
Merck | 14,8061 |
BRN | 91867 |
pKa | 8.52(at 25℃) |
PH | 9.0 (0.5g/l, H2O, 20℃) |
Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
Sensitive | 2: reacts with aqueous acid |
Refractive Index | 1.6250 (estimate) |
MDL | MFCD00198096 |
Physical and Chemical Properties | Quinine, also known as cinchona Frost and cinchona alkaloid, is the main alkaloid in the bark of cinchona tree and its genus. Cinchona bark contains more than 20 kinds of alkaloids. In addition to quinine, Quinidine has anti-malaria effect, cinchonidine and cinchonidine. All alkaloids from cinchona bark are used as antimalarial and antipyretic drugs, called cinchona total alkaloids or quinine. Quinine belongs to quinolines chemically and is an isomer of quinidine. White amorphous powder or crystal, odorless, bitter taste. Melting point 172.8 ° C, there is a left optical rotation, [alpha] D20-168 (ethanol). Soluble in ethanol, chloroform, benzene, ether, water-soluble. The dilute sulfuric acid solution has blue fluorescence, drop of bromine water and excess ammonia, that is, a green. Cinchona bark powder with lime and sodium hydroxide treatment, kerosene extraction, dilute sulfuric acid neutralization, precipitation of quinine sulfate and ammonia will be obtained. It can also be synthesized from M-hydroxybenzaldehyde and α-aminoacetaldehyde. For the treatment and prevention of various malaria, medicinal for its sulfate or hydrochloride. quinine sulfate: it is white fine needle-like crystal, soft, easy to compress, odorless, bitter in taste, gradually Brown in sunlight, and its saturated aqueous solution is levorotatory, and neutral reaction, slightly soluble in water and ethanol. quinine hydrochloride: colorless or white mercerized needle-like crystals, odorless, bitter taste, gradual discoloration in the sun, weathering, soluble in water, easily soluble in boiling water, soluble in ethanol or chloroform. quinine dihydrochloride: white powder, odorless, extremely bitter in taste, gradually discolored in sunlight, acidic in aqueous solution, Very soluble in water, soluble in ethanol, chloroform-soluble, insoluble in ether. Important derivatives of quinine such as ethyl carbonate (superior quinine), because of no bitter taste, also known as "tasteless quinine", for oral use in children. The above information was compiled by Tong Tong. |
Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R42/43 - May cause sensitization by inhalation and skin contact. R22 - Harmful if swallowed R20/22 - Harmful by inhalation and if swallowed. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R36/38 - Irritating to eyes and skin. |
Safety Description | S22 - Do not breathe dust. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37/39 - Wear suitable gloves and eye/face protection S36 - Wear suitable protective clothing. S7 - Keep container tightly closed. |
UN IDs | 1544 |
WGK Germany | 3 |
RTECS | VA6020000 |
FLUKA BRAND F CODES | 8 |
HS Code | 29392110 |
Hazard Class | 6.1(b) |
Packing Group | III |
Toxicity | Antimalarial still used primarily for treatment of plasmodium resistant to synthetic antimalarials. Also used as antipyretic for colds, influenza, and cramp; quinine may have toxic effects on the eye, apparently due to an immune reaction, and may also affect male reproductive capacity. |
Reference Show more | 1. Wu Haibo, Ren Guifeng, Liu Songyong, et al. Study on the Effect of Demulsification Method on the Quality of Oil Recovered from Emulsion and the Flavor of Hydrolyzed Protein in the Process of Aqueous Enzymatic Extraction of Soybean Oil [J]. Food Industry Science and Technology, 2020, 041(004):133-138,145. 2. Jiang Lianzhou, Tong Xiaohong, Liu Baohua, etc. Effects of Enzyme Types on Functionality and Bitterness of Biodissociated Soybean Protease Hydrolysates [J]. Journal of Agricultural Machinery, 2018, v.49(08):368-374. |
It is mainly found in the bark or root bark of the red cinchona tree or the cinchona tree. The quinine crystallized in benzene is a needle-like crystal containing a solvent, which slowly loses the solvent in the air and becomes a tiny crystalline anhydrous. Insoluble in water, soluble in ethanol, chloroform and boiling benzene, soluble in anhydrous ether (1:250). There are two nitrogen atoms in the quinine molecule, in which the nitrogen atom of the quinine nucleus is in the state of tertiary amine, and the alkali is strong, and the salt can be formed with the acid, which has a strong bitter taste. Quine sulfate is a white fine needle-like crystal, gentle, easy to compress, odorless, extremely bitter, light-colored, soluble in chloroform-anhydrous ethanol (2:1) mixture, slightly soluble in water, ethanol, chloroform and ether.
The bark or root bark of cinchona was removed, dried, and mixed with soda lime after crushing. After repeated extraction with petroleum ether, the extracts were combined and clarified, diluted sulfuric acid was added for extraction. After the acid layer was concentrated and crystallized, quinine sulfate was obtained. The finished product is present in two forms, acidic quinine sulfate and neutral quinine sulfate. Acidic quinine sulfate is a salt formed by a molecule of sulfuric acid and a molecule of quinine, which is water-soluble and acidic in aqueous solution. Neutral quinine sulfate is a salt formed by two molecules of quinine and one sulfuric acid, and its aqueous solution is neutral but water-soluble. Acidic quinine sulfate is commonly used in medicine.
quinine is an important antimalarial drug because it can inhibit the reproduction or kill the erythrocytic protozoan of p. Falciparum. Quinine also inhibits myocardial contractility and increases the rhythmic contraction of the uterus.