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Quinine sulfate dihydrate is a quinine alkaloid, also known as cinchona alkaloid, chemical name: (8s, 9R) -6 '- methoxy-cinchona-9-alcohol sulfate dihydrate, pure white needle-like crystal, generally dull. Soluble in hot water (i:35) and alcohol (i:125), insoluble in chloroform and ether. Darken brown when exposed to light. It is odorless and has a strong, lasting bitter taste. It is a quinoline derivative, which can combine with the DNA of Plasmodium to form a complex to inhibit DNA replication and RNA transcription, thus inhibiting the protein synthesis of Plasmodium. Its effect is weaker than that of chloroquine. This product's terminal drug applies to chloroquine and falciparum malaria caused by multi-drug resistant strains. It can also be used to treat vivax malaria. It should be used with caution in patients with asthma, atrial fibrillation, severe other heart diseases, glucose-6-phosphate dehydrogenase deficiency, and women during their menstrual period. This product is for laboratory use only.
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Chemical Formula |
C20H30N2O8S |
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Exact Mass |
458 |
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Molecular Weight |
459 |
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m/z |
458 (100.0%), 459 (21.6%), 460 (4.5%), 460 (2.2%), 460 (1.6%) |
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Elemental Analysis |
C, 52.39; H, 6.60; N, 6.11; O, 27.91; S, 6.99 |
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The most effective form of quinine for malaria treatment was discovered in 1737. In 1820, two French chemists Pelletier and cavernous, separated from the bark of quia and called it quinine or quinine. The name comes from the tree name Quina Quina in Inca. It began to be used on a large scale around 1850. Quinine sulfate and quinine hydrochloride are white crystals with an extremely bitter taste. The former is slightly soluble in water for oral use, while the latter is easily soluble in water for injection.
There are many methods for synthesizing Quinine Sulfate Dihydrate, among which the following are several common synthesis methods:
1. Tollard synthesis
This is a classic synthesis method, mainly achieved through the following steps:
-Firstly, it will have α- Ketone compounds with naphthoquinone structure (such as 1-hydroxy-2- Methoxy group naphthalene) and α- Ethyl formate reaction, forming α- Carbamate.
-Will α- Carbamate reacts with amine compounds (such as thioacetamide) with sulfhydryl group to generate α- Carbamate thiol ester.
- α- Quinine is formed by hydrolysis, ammonolysis, and bromination reactions of thiol carbamate ester.
2 Stork synthesis
This is another commonly used synthesis method, with the following steps:
-Using Guanine as the starting material, valeric acid is formed through a series of chemical reactions.
-Valeric acid is gradually converted into hydroxyquinoline through several steps, including acyl chlorination reaction, Substitution reaction, etc.
-Hydroxyquinoline undergoes multiple steps, including acylation, reduction, etc., to ultimately obtain Quinine.
3 Cinchonitine method
This method starts with cinchona alkaloid and undergoes a series of chemical reactions to ultimately synthesize Quinine.
-Firstly, the hydrogenation reaction of cinchona alkaloids is carried out to obtain cinchona alkaloids.
-Quinine is gradually converted into quinine through multiple reactions, including rearrangement, oxidation, etc
Melting point ~225 ° C (Dec.) (lit.), Specific rotation -245 º (c=2, 0.1M HCl), FEMA 2977 | QUININE SULFATE, Keep in a dark place, sealed in dry, 2-8 ° C, Solubility in a mixture of chloroform and absolute alcohol (2:1), Morphology crystal powder, Color light yellow or beige to brown, Water solubility 0.12 g/100 ml (20 º C), Light sensitive, Merck 14,8061, BRN 6113937, Stable Incompatible with potent oxidizing agents, alkalies, ammonia, strong bases, iodine.
The pharmacological effect of Quinine Sulfate Dihydrate is that quinine is a quinoline derivative, which can combine with the DNA of Plasmodium to form a complex to inhibit DNA replication and RNA transcription, thus inhibiting the protein synthesis of Plasmodium. Its effect is weaker than that of chloroquine. In addition, quinine can reduce the oxygen consumption of Plasmodium, resist the phosphorylase in Plasmodium and interfere with its glucose metabolism. Quinine also causes malarial pigment aggregation, but the development of chemicalbook is slow, rarely forming large clumps, and often accompanied by cell death. Electron microscope observation showed that the nucleus and outer membrane of the protozoa were swollen, and there were small vacuoles. The blood cell particles aggregated in the small vacuoles, different from the pigment agglutination of chloroquine. In the blood, a particular concentration of quinine can lead to premature rupture of parasitized red blood cells, thus preventing the maturation of schizonts.
The discovery history of Quinine Sulfate Dihydrate can be traced back to the 17th century. Here are some key historical milestones:
Early use: This substance was used as a component of the bark of the cinchona tree and was first used to treat malaria in the 1600s. At that time, it was called "Jesuit bark", "Cardinal bark" or "Holy bark". This name originated from Jesuit missionaries using it in South America in 1630, although there are legends indicating that the locals had already used it earlier.
Legend: There is a legend about an Indian who got lost in the Andes jungle due to a high fever. After drinking a pool of bitter stagnant water, he found that the water was contaminated by the surrounding cinchona trees and thought he was poisoned. But surprisingly, his fever quickly subsided, and he shared this accidental discovery with the villagers. Afterwards, they used extracts from the bark of cinchona trees to treat the fever.
Introduced to Europe: Another widely accepted legend about the discovery of quinine involves Countess Chinjo of Spain, who contracted a fever in Peru and was cured by the bark of a tree. When she returned to Spain, she brought the substance to Europe. In 1742, botanist Carl Linnaeus named this tree "cinchona" in her honor.
Extraction and Naming：Naming: In 1742, Carl Linnaeus officially named this tree "Cinchona" in honor of Count Chinchon and his wife Ana. The name Quinine comes from the Peruvian word Kina, meaning "bark"; Extraction: In 1817, French pharmacists Caventou and Pelletier collaborated to isolate quinine monomers from the bark of cinchona, confirming that quinine is an effective anti malarial ingredient in cinchona bark.
Chemical structure research: With the deepening of research, scientists have successively determined its stereochemical structure, molecular formula C20H24N2O2, as well as its complex stereosynthesis and biological activity studies. This structural analysis reveals the presence of a quinoline core, one terminal alkene double bond, one methoxy group, one hydroxyl group, and a bridged nitrogen-containing bicyclic ring with four chiral centers. These data provide strong evidence for its structure.
adverse reaction
Quinine Sulfate Dihydrate is an alkaloid extracted from the bark of cinchona chinensis, which has various pharmacological effects such as anti malaria, antipyretic, analgesic, and anti arrhythmic. As a classic antimalarial drug, it was once the first choice for treating malaria, especially in areas where chloroquine resistant malaria is prevalent, it still holds an important position. However, its use is accompanied by a series of adverse reactions involving multiple systems, and in severe cases, it can be life-threatening.
Adverse reactions in the blood system
Mechanism: Quinine can induce immune-mediated platelet destruction, leading to a decrease in platelet count.
Clinical manifestations: Skin bruising, nosebleeds, gum bleeding, and in severe cases, intracranial hemorrhage may occur.
Clinical data:
A prospective study showed that in patients with malaria treated with quinine sulfate dihydrate, the incidence of thrombocytopenia (platelets<100 × 10 ⁹/L) was 8%, of which 2% were severe thrombocytopenia (<50 × 10 ⁹/L).
Case report: A 28 year old female patient received treatment with quinine sulfate dihydrate for malaria. On the 5th day, her platelet count decreased from 150 × 10 ⁹/L to 30 × 10 ⁹/L. After discontinuing the medication and administering glucocorticoids, her platelet count gradually recovered.
Hemolytic anemia
Mechanism: Quinine can induce oxidative hemolysis in patients with glucose-6-phosphate dehydrogenase (G6PD) deficiency.
Clinical manifestations: jaundice, anemia, hemoglobinuria, and in severe cases, acute kidney failure may occur.
Clinical data: The incidence of hemolytic anemia in G6PD deficiency patients can reach 10% -20%.
Suggestion for treatment: Screen for G6PD deficiency before treatment and avoid using it for individuals with known G6PD deficiency; Immediate discontinuation of medication and supportive treatment (such as blood transfusion or alkalinization of urine) is required when hemolysis occurs.
Mechanism: Quinine may induce DIC by activating the coagulation system or damaging endothelial cells.
Clinical manifestations: bleeding and thrombosis coexist, laboratory tests show thrombocytopenia, prolonged prothrombin time, and decreased fibrinogen.
Case report: A 65 year old male patient received treatment with quinine sulfate dihydrate for malaria. On the 7th day, he developed extensive skin bruising and hematuria. The coagulation test confirmed the diagnosis of DIC. After discontinuing the medication and administering heparin and fresh frozen plasma, his condition improved.
Cardiovascular system adverse reactions
Arrhythmia
Mechanism: Quinine can inhibit the myocardial conduction system, prolong the QT interval, and induce apical torsion type ventricular tachycardia (TdP).
Clinical manifestations: palpitations, dizziness, fainting, and in severe cases, cardiac arrest may occur.
Clinical data: A study involving 100 malaria patients showed that the incidence of QT interval prolongation (>450ms) during treatment with quinine sulfate dihydrate was 15%, with 3% developing into TdP.
Hypotension
Mechanism: Quinine can dilate peripheral blood vessels, reduce peripheral resistance, and lead to a decrease in blood pressure.
Clinical manifestations: Dizziness, fatigue, cold sweat, and in severe cases, shock may occur.
Suggestion for treatment: Monitor blood pressure during treatment and avoid rapid intravenous administration; When hypotension occurs, fluid replacement and the use of vasoactive drugs are necessary.
Frequently Asked Questions
Why is its most revered role in the field of analytical chemistry unrelated to anti malaria?
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It is the world's first fluorescent standard reference material (SRM). In 1980, NBS (now NIST) in the United States certified it as a first-class standard for fluorescence quantum yield, used to calibrate fluorescence spectrometers worldwide. Its corrected emission spectrum in 0.1 mol/L HClO ₄ is still a classic reference in fluorescence determination.
Why is the crystal water content of its "dihydrate" a mandatory standard in the USP Pharmacopoeia?
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USP stipulates that its moisture content must be between 4.0% and 5.5% (theoretical value is about 4.6%). Excessive moisture can cause clumping and accelerate oxidation discoloration; If it is too low, the lattice will collapse, leading to abnormal dissolution rate and deviation in specific rotation. The pharmacopoeia ensures consistency and bioequivalence between batches by strictly controlling weight loss.
The "bitterness" of quinine not only comes from the tongue, but what other "non taste" niche receptor targets does it have in the human body?
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It is an agonist of the T2R4 bitter taste receptor. This receptor is not only present in taste buds, but also widely distributed in airway smooth muscle, testes, brain, and intestines. Activating airway T2R4 can dilate the bronchi (a completely different mechanism than conventional beta agonists), while activating macrophage T2R4 can inhibit Rac1 GTPase activity, regulate cytoskeleton and immune migration.
Why does the pharmacopoeia specifically set a limit test for "dihydroquinine sulfate"? Where does this impurity come from?
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Dihydroquinine is a natural associated alkaloid of quinine (derived from the bark of cinchona bark), with very similar chemical properties, and is difficult to remove through conventional isolation. It has pharmacological activity but weak antimalarial potency. USP stipulates that its peak response value should not exceed 1/9 (≤ 10.0%) of the main peak of quinine to ensure the uniformity of the potency of the active pharmaceutical ingredient.
What is the mechanism behind the gradual brown color change of its powder when exposed to light?
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This is the photooxidation reaction of quinine ring. Under ultraviolet or strong sunlight, the nitrogen atom of the quinoline ring is oxidized to form nitrogen oxides and polymers, and the solution changes from colorless fluorescent blue to yellow or brown, while the fluorescence quantum yield significantly decreases. This means that if a standard curve is prepared under light, it will lead to systematic underestimation of fluorescence intensity and quantitative deviation. This is a "stability black hole" that beginners are prone to fall into and is rarely emphasized in literature.
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