Pure quinine powder, the core component of quinine, also known as cinchona cream and cinchona alkali, is the main alkaloid in the bark of the Rubiaceae plant cinchona tree and its congeners. Cinchona bark contains more than 20 alkaloids. In addition to quinine, quinidine, cinchonine, and cinchonidine have antimalarial effects. All alkaloids from cinchona bark are used as antimalarial and antipyretic drugs, which are called cinchona total alkali or total quinine. Quinine exists in the form of white crystals, presenting a colorless or slightly yellow appearance. Molecular formula C20H24N2O2, CAS 130-95-0. Its crystals are columnar or needle shaped. The solubility in water is relatively low, approximately 0.16 g/100 mL (20 ° C). But it can dissolve better under acidic conditions. It can dissolve in many organic solvents, such as alcohols, ethers, ketones, and esters. It has optical activity and belongs to chiral molecules. Its optical rotation is[ α]_ D ^ 25=+219 ° (concentration: 1 g/100 mL methanol). The optical activity is due to the chiral center of Quinine molecules. The structure of the crystal can be analyzed using X-ray diffraction technology. It belongs to the Monoclinic crystal system, and the cell parameters can be obtained in the relevant literature. The pKa value (acidity constant) is approximately 8.4, and within this pH range, it exists in the form of positively charged ions. It is a fluorescent compound with luminescent properties. Under UV excitation, Quinine solution exhibits blue fluorescence. This characteristic makes it widely used as a fluorescent probe and dye in many applications.
Quinine belongs to quinoline and is an isomer with quinidine. White amorphous powder or crystal, odorless, and extremely bitter. It has left-handed optical property[ α] D20-168 ° (ethanol). Soluble in ethanol, chloroform, benzene, and ether, slightly soluble in water. The dilute sulfuric acid solution has blue fluorescence. When bromine water and excess ammonia are added dropwise, it shows emerald green. Cinchona bark powder is treated with lime and sodium hydroxide, extracted with kerosene, neutralized with dilute sulfuric acid, and the precipitated quinine sulfate is obtained by reacting with ammonia. It can also be mixed with m-Hydroxybenzaldehyde α- Aminoacetaldehyde as raw material. It is used to treat and prevent all kinds of malaria, and its medicine is sulfate or hydrochloride.
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Chemical Formula |
C20H24N2O2 |
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Exact Mass |
324 |
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Molecular Weight |
324 |
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m/z |
324 (100.0%), 325 (21.6%), 326 (2.2%) |
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Elemental Analysis |
C, 74.05; H, 7.46; N, 8.63; O, 9.86 |
Pure Quinine Powder is a multifunctional substance that has been widely used in many fields.
1. Antimalarial drugs:
As the earliest discovered and widely used use, Quinine is a powerful antimalarial drug. It is used to treat malaria, especially malaria caused by Plasmodium, such as vivax malaria and falciparum malaria. Quinine achieves therapeutic effects by disrupting the metabolic process of malaria parasites, especially by interfering with the parasite's heme degradation pathway.
2. Antipyretic and analgesic effects:
Quinine also has a certain antipyretic and analgesic effect. It can alleviate fever and pain symptoms caused by infection, fever, or other inflammations. However, due to the existence of more effective and safe antipyretic and analgesic drugs, there are relatively few clinical applications of quinine for antipyretic and analgesic.
3. Muscle relaxant:
Quinine has a muscle relaxation effect and can alleviate some symptoms related to muscle tension and spasms. Therefore, it is widely used to treat symptoms such as muscle spasms and tics. However, when using Quinine as a Muscle relaxant, it needs to be used carefully and follow the doctor's advice, because it has some toxic and side effects.
4. Antiarrhythmic drugs:
Quinine is also used as an antiarrhythmic drug due to its ability to affect heart rhythm. It has shown certain effects in the treatment of certain types of arrhythmia, such as Atrial fibrillation and ventricular tachycardia. However, due to the existence of safer and more effective alternative drugs, Quinine has relatively few clinical applications in this area.
5. Cocktail additives:
Quinine is used as a cocktail additive in the beverage industry, especially in classic Tony water. Quinine endows Tony's water with a bitter taste and unique flavor, making it one of the important ingredients in many classic cocktails.
6. Optical materials:
Due to its fluorescent properties and the ability to emit blue fluorescence, Quinine has certain applications in the field of optical materials. Quinine is used as a fluorescent probe and labeling molecule, playing a role in biological imaging, fluorescence sensors, and fluorescence microscopy.
7. Cosmetics:
Quinine is also used as an ingredient in cosmetics to provide the aroma and fluorescence effects of certain products. It can be used in perfume, shampoo, skin care products and other products.
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Quinine's laboratory synthesis method is complex and typically requires multiple steps and multiple raw materials. The following is a general strategy for synthesizing Quinine:
Quinine typically starts with carbon tetrachloride and isopropylamine as starting materials. The reaction of these raw materials will produce dichloroisopropylamine.
React dichloroisopropylamine with formaldehyde to form a five membered ring intermediate. Subsequently, after multiple reactions, the five membered ring intermediate is converted into a seven membered ring intermediate.
The construction of seven membered ring intermediates involves multiple steps, such as aromatization, oxidation, and cyclization. One of the Committed step is to dechlorine one carbon atom in the ring with Sodium cyanide, and then further react with other reactants.
After the formation of the seven membered ring intermediate, a series of modification reactions are required. These modification reactions include the introduction of substituents, Redox, carbonyl protection and deprotection to gradually build the structure of target molecules.
After the formation of Quinine's structure, additional reactions are required to generate the target product. These reactions include the introduction of substituents, the oxidation and reduction of hydrocarbons, and the protection and deprotection of hydroxyl groups.
Overall, Quinine's laboratory synthesis is a challenging task that requires experienced organic chemists and advanced synthesis techniques. I hope this brief overview is helpful to you. For more detailed information, please refer to relevant scientific literature.
Melting point 173-175 ° C (lit.), Specific rotation - 172 º (C = 1, EtOH), Boiling point 462.75 ° C (rough estimate), Density 1.1294 (rough estimate), Refractive index 1.6250 (estimated), Flash point > 110 ° C (> 230 ° f), Keep in dark place, insert atmosphere, room temperature, Solubility H2O: solid, Acidity coefficient (PKA) 8.52 (at 25 ℃), Morphology crystal powder, Color white, PH value 9.0 (0.5g/l, H2O, 20 ℃), PH value range of acid-base indicator discoloration blue I uorescence (3.0) to weak violet I uorescence (5.0); Weak violet I uorescence (9.5) to nonI uorescence (10.0), Optical activity[ α] 25/D 165°, c = 2 in ethanol, Water solubility, Light sensitive, Hydrolysis sensitivity 2: reactions with acute acid, BRN 91867, It mainly applies bird representatives, sunscreen, antimalarial agent, antiviral agent, antitumor agent, drug coated coronaryagent, antiparasitic agent, treatment of epilepsy, skeletal muscle spam, drug coated coronary stent system.
The pharmacological action of pure quinine powder is one of the oldest antimalarial drugs. As early as the 15th century, cinchona bark containing quinine has become a specific drug widely used to treat malaria. Its antimalarial effect is similar to chloroquine and works by interfering with DNA synthesis. It can inhibit the erythrocytic phase of various malaria parasites and control the onset of malaria symptoms. It can also kill the gametophytes of vivax malaria and Plasmodium vivax. But it has no effect on the extraerythrocytic phase. Its main advantage is that it is not easy to develop drug resistance. The DNA binding mode between quinine and Plasmodium may be different from that of chloroquine, so it has no cross-resistance and can be used to resist the infection of chloroquine strains (especially Plasmodium falciparum). In addition, quinine can also stimulate the uterus, inhibit the myocardium, and relieve fever and pain. The physical and chemical properties of quinine powder can be used as the detection agent of bismuth, platinum, and other metal ions in analytical chemistry. It can also be used as the separation agent of racemic organic acids.
Quinine was also the first drug used to treat malaria. Quinine is used as a muscle relaxant by the indigenous Quechua people of Peru, Bolivia, and Ecuador to treat tremors caused by low temperatures. The Quechua people mix the bark of the cinchona tree with sweet water to counteract the bitterness of the bark and make tonic water.
The Jesuits were the first to bring the Golden Rooster to Europe. Spaniards were aware of the medicinal value of cinchona bark in the 1770s or earlier: Nicolas Monades (1571) and Juan Fragoso (1572) both described a tree later identified as cinchona, whose bark was used to produce beverages for treating diarrhea. Quinine has been used by Europeans in its unpurified form since at least the early 17th century.
In 1631, it was first used in Rome to treat malaria. In the 17th century, malaria was an endemic disease in the swamps and wetlands surrounding the city of Rome. Malaria has caused the deaths of several popes, many cardinals, and countless ordinary Roman citizens. Most priests trained in Rome have seen malaria patients and are familiar with the symptoms of tremors during the fever phase of the disease. A pharmacist trained in Lima, Jesuit monk Agostino Salebino (1564-1642), observed that the Quechua people used the bark of the cinchona tree to treat malaria. Although its effectiveness in treating malaria (and tremors caused by malaria) is not related to its effectiveness in treating chills, it is a successful anti malaria drug. Soon, Salenbino sent a small number of personnel to Rome for malaria treatment trials. In the following years, cinchona bark, also known as Jesuit bark or Peruvian bark, became one of the most valuable commodities shipped from Peru to Europe. When King Charles II used quinine to cure malaria in the late 17th century, it became popular in London. It was the preferred antimalarial drug until it was replaced by other drugs in the 1940s.
Charlie Marie de la Condomin discovered quinine, the most effective treatment for malaria, in 1737. In 1820, French researchers Pierre Joseph Pertier and Joseph Benem Cavantou first isolated quinine from the bark of the genus Aquinas and subsequently named the substance Aquinas. This name comes from the original Inca word for cinchona bark, quina or quinaquina, meaning "bark of the bark" or "sacred bark". Before 1820, tree bark was first dried, ground into fine powder, mixed into a liquid (usually wine), and then consumed. The large-scale use of quinine as a malaria preventive drug began around 1850. In 1853, Paul Bullitt published a brief history and literary discussion of Quina.
Quinine played an important role in European colonial rule over Africa. Quinine is considered the main reason why Africa is no longer referred to as a 'white tomb'. A historian once said, 'The efficacy of quinine gave colonizers new opportunities to flood into the Gold Coast, Nigeria, and other regions of West Africa.'.
In order to maintain its monopoly on cinchona bark, Peru and its neighboring countries began banning the export of cinchona seeds and saplings in the early 19th century. The Dutch government continued to smuggle quinine seeds, and in the late 19th century, the Dutch planted this plant in Indonesian plantations. They quickly became the main supplier of the factory and established Kina Bureau in 1913, a monopoly group responsible for controlling prices and production. By the 1930s, Dutch plantations in Java had produced 22 million pounds of cinchona bark, accounting for 97% of the world's quinine production. The United States attempted to sue Kina Bureau, but was unsuccessful. During World War II, Germany occupied the Netherlands, while Japan cut off the supply of quinine to the Allied powers while controlling the Philippines and Indonesia. The United States obtained 4 million cinchona seeds from the Philippines and began operating cinchona plantations in Costa Rica. But these supplies arrived too late, and thousands of American troops stationed in Africa and the South Pacific died due to a lack of quinine. Despite controlling the supply of quinine, the Japanese did not effectively utilize it, resulting in thousands of Japanese troops being killed in the Southwest Pacific. Quinine has always been the preferred drug for anti malaria until after World War II, when other drugs with fewer side effects, such as chloroquine, basically replaced quinine.
What are the side effects of this compound?
Eye toxicity
It may have toxic effects on the eyes, usually caused by immune reactions. Therefore, when using it, special attention should be paid to its possible impact on the eyes.
Reproductive impact
It may also affect male reproductive ability, which is an important consideration for men with fertility needs.
Drug resistance
mainly used to treat malaria parasite infections that develop resistance to synthetic antimalarial drugs. However, long-term use of quinine may lead to malaria parasites developing resistance to it, thereby reducing the effectiveness of treatment.
Other side effects
It may also cause a series of other side effects, including but not limited to nausea, vomiting, headache, dizziness, tinnitus, rash, etc. In addition, quinine may also affect heart function, leading to problems such as arrhythmia.
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