Cinchonine CAS 118-10-5

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Cinchonine, molecular formula C19H22N2O, CAS 118-10-5, It is a colorless needle shaped or prismatic crystal. Melting point 265 ℃ (sublimation starts at 220 ℃), optical rotation [α]+229 ° (ethanol); Each gram is soluble in 60 milliliters of ethanol, 25 milliliters of boiling water, 110 milliliters of chloroform, or 500 milliliters of ether, and almost insoluble in cold water; The median lethal dose is 152 milligrams per kilogram. A quinoline alkaloid. The molecular formula is C19H22N2O and the molecular weight is 294.39. In 1820, by P- J. Petier et al. first isolated it. It exists in the family Rubiaceae and is found in the golden chicken tree.

Xinkening hydrochloride decomposes at around 275 ℃, easily soluble in water or ethanol, slightly soluble in chloroform, and difficult to dissolve in ether; Its sulfate melting point is 206-207 ℃, easily soluble in water or ethanol, slightly soluble in chloroform, and difficult to dissolve in ether. Xinkening is a diastereomer of Xinkening, with a melting point of 210 ℃ [α] -109.2 ° (ethanol) and a median lethal dose of 206 mg/kg. Used for the determination of molybdenum and tungsten, photometric determination of bismuth, and calibration of bismuth, antimony, germanium, cadmium, molybdenum, and tungsten. Separation of racemic organic acids. Used as a reagent for the determination of bismuth, silver, mercury, lead, antimony, vanadium, copper, and platinum ions by thin-layer chromatography. It is also used as an indicator for precipitation titration to determine iodide.

Cinchonine is a quinoline alkaloid with a molecular formula of C19H22N2O and a molecular weight of approximately 294.39. It exists in plants of the Rubiaceae family, such as the red cinchona tree and the cinchona tree. Xinkening is a colorless needle shaped or prismatic crystal with a melting point of 265 ° C and a specific optical rotation of+229 ° (in ethanol). The hydrochloride salt of Xinkening is easily soluble in water or ethanol, slightly soluble in chloroform, and difficult to dissolve in ether; Its sulfate has a melting point of 206-207 ° C and is also easily soluble in water or ethanol. The median lethal dose of Xinkening is 152 milligrams per kilogram, indicating its toxicity.

Cinchonine is used for the determination of molybdenum and tungsten, photometric determination of bismuth, and the determination of bismuth, antimony, germanium, cadmium, molybdenum and tungsten. Resolution of racemic organic acids. It is used as a reagent for the determination of bismuth, silver, mercury, lead, antimony, vanadium, copper and platinum ions by thin-layer chromatography. It is also used as an indicator for the determination of iodide by precipitation titration.

1. Pharmaceutical field

 

Xinkening has pharmacological effects such as anti malaria, anti-tumor, anti-inflammatory, and analgesic. It can be used to treat malaria and has inhibitory effects on certain tumor cells, promoting early apoptosis of tumor cells. Research has shown that Xinkening can inhibit tumor cell growth, promote early apoptosis of tumors, and enhance the expression of pro apoptotic factors while inhibiting the expression of anti apoptotic factors. Therefore, Xinkening is expected to have a wider range of applications in anti-tumor fields in the future. In addition, the hydrochloride salt of Xinkening can be used to treat arrhythmias, especially those that develop resistance to known conventional drugs.

2. Chemical industry field

 

Xinkening and its derivatives are widely used in the preparation, separation, and analysis of chiral drugs and chiral intermediates. Chiral drugs refer to drug molecules with specific stereoisomers, whose pharmacological and pharmacokinetic properties often differ from those of enantiomers. Xinkening, as a chiral catalyst or ligand, plays an important role in asymmetric synthesis reactions, helping to synthesize chiral drugs with specific stereoconfigurations. In addition, Xinkening is also an important reagent for determining metals such as molybdenum, tungsten, bismuth, etc.

3. Agricultural field

 

Although there is limited specific information, Xin Kening may have potential applications in the agricultural field. For example, it may be used as an insecticide or fungicide to prevent and control crop pests and diseases. However, further research is needed to confirm the application in this field.

 

 

1. Anti malaria effect
Xinkening has a certain inhibitory effect on malaria parasites and can be used to treat malaria. Although its antimalarial effect is weaker than quinine (another type of cinchona alkaloid), it can still be used as an antimalarial drug in some cases.

2. Antitumor effect
Xinkening has inhibitory effects on certain tumor cells and can promote early apoptosis of tumor cells. Research has shown that Xinkening exerts anti-tumor effects by enhancing the expression of apoptosis promoting factors and inhibiting the expression of apoptosis inhibiting factors. This discovery provides experimental evidence for the application of Xinkening in the field of anti-tumor.

 

3. Antiarrhythmic effect
The hydrochloride salt of Xinkening can be used to treat arrhythmias, especially those that develop resistance to known conventional drugs. However, due to the low solubility of Xinkening hydrochloride in water, its oral administration is limited to some extent. Therefore, developing new administration methods or drug combinations to improve their bioavailability is one of the future research directions.

1. Chiral drug synthesis
Xinkening, as a chiral catalyst or ligand, plays an important role in asymmetric synthesis reactions. For example, using Xin Kening to catalyze asymmetric epoxidation reactions, chiral epoxides with specific stereoisomers can be synthesized, which have important applications in drug synthesis.

2. Metal determination reagents
Xinkening is an important reagent for determining metals such as molybdenum, tungsten, bismuth, etc. Xinkening is an essential analytical reagent in the weight analysis of tungsten ore. In addition, Xinkening can also be used for the determination of bismuth, silver, mercury, lead, antimony, vanadium, copper, platinum ions, etc. by thin-layer chromatography.

Synthetic cinchonine:

1. Plant sources include the bark of Rubiaceae plant red Cinchona, the bark of Cinchona, etc. It can also be synthesized and made into hydrochloride and tartrate. It has antimalarial and antipyretic effects.

2. Cinchona bark can be extracted to obtain alkaloids. The crude product is dissolved in nitric acid, and then precipitated with ammonia. The white precipitate obtained is cinchonin.

3. Chemical preparation:

(1) Preparation of raw material a: mix cinchona bark (30 ~ 60 mesh powder) with toluene, heat it, refluxe it, soak it and concentrate it. The total alkaloid extract obtained is dissolved in dilute sulfuric acid solution. After filtration, heat the filtrate, add sodium hydroxide under stirring to adjust the pH value of the solution, and cool it after standing. Quinine sulfate is separated out, and quinine sulfate solid is filtered out. Then add sodium hydroxide solution to the filtrate, place it, separate out the total solids of the remaining cinchona alkaloids, filter out the solids, and dry under normal pressure to obtain raw material a.

(2) Take raw material a, add ethyl acetate, stir at room temperature, stand still, and filter to obtain filtrate B and insoluble substance C. After concentrating filtrate B, place it at room temperature to crystallize and precipitate completely. After filtration and crystallization, dissolve it in ethanol solution, decolorize and recrystallize it with activated carbon to obtain white solid with a yield of 34%. It is a white amorphous or crystalline powder, which is soluble in ethanol, easily soluble in chloroform, slightly soluble in ether. The content determined by perchloric acid titration is 99.6%; The identification result of the white solid sample by thin-layer chromatography is consistent with that of the standard. The melting point of the sample does not change after mixing with the standard, which confirms that the white solid is quinidine. Dissolve the insoluble substance C with ethanol, add activated carbon, decolorize under stirring, filter and remove the activated carbon to obtain 0.72g white crystalline powder with a yield of 21%. The appearance of this product is white powder, which is dissolved in ethanol and chloroform, slightly soluble in ether, and the content is 98.5% determined by perchloric acid titration. The identification result of the sample by thin layer chromatography is consistent with that of the standard. The melting point of the sample does not change after mixing with the standard. It is identified that the white powder is cinchonin.

The resurgence of interest in natural products has revitalized research on cinchonine. Key areas of exploration include:

Structure-Activity Relationships (SAR): Modifying cinchonine's quinoline and piperidine rings to enhance potency and reduce toxicity.

Nanotechnology: Encapsulating cinchonine in liposomes or polymeric nanoparticles to improve bioavailability and target specific tissues.

Combination Therapies: Pairing cinchonine with chemotherapeutic agents or immunotherapies to overcome resistance mechanisms.

Additionally, sustainable cultivation of Cinchona species and biotechnological approaches (e.g., yeast-based biosynthesis) could address supply chain challenges and reduce environmental impact.

Cinchonine exemplifies the enduring value of natural products in modern medicine. From its origins as a malaria remedy to its emerging roles in oncology, endocrinology, and green chemistry, this alkaloid continues to inspire innovation. Its structural complexity, multifaceted mechanisms, and relatively favorable safety profile position it as a promising candidate for drug repurposing and novel therapeutic development. As research unravels its full potential, cinchonine may well secure its place among the most versatile compounds derived from nature, bridging historical wisdom with cutting-edge science.

Cinchonine's future is being reshaped by convergence of scientific innovation, sustainable practices, and geopolitical shifts. While challenges persist, the compound's versatility-from life-saving drugs to eco-friendly pesticides-ensures its relevance in a post-pandemic world prioritizing health and sustainability. Stakeholders who navigate the complexities of supply chain ethics, regulatory compliance, and technological disruption will define the next chapter of this ancient alkaloid's story.

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