Quinina
Descripción general
Descripción
La quinina es un alcaloide natural que se deriva de la corteza del árbol de quina, originario de las regiones andinas de América del Sur. Históricamente, se ha utilizado como un fármaco antimalárico y es conocido por su sabor amargo, que también se utiliza en el agua tónica. La this compound se aisló por primera vez en 1820 y ha desempeñado un papel crucial en el tratamiento de la malaria, especialmente antes de la llegada de los fármacos antimaláricos sintéticos .
Mecanismo De Acción
La quinina ejerce sus efectos antimaláricos interfiriendo con la capacidad del parásito para digerir la hemoglobina. Inhibe la formación de hemozoína, un subproducto tóxico de la digestión de la hemoglobina, lo que lleva a la acumulación de hemo libre, que es tóxico para el parásito. Esto resulta en la muerte del parásito de la malaria . Además, la this compound afecta la membrana muscular y los canales de sodio, lo que explica su uso en el tratamiento de trastornos musculares .
Compuestos similares:
Cloroquina: Otro fármaco antimalárico que es más eficaz en suprimir el crecimiento de las formas sanguíneas del parásito de la malaria.
Artemeter y lumefantrina: Estos se utilizan en terapias combinadas para la malaria y tienen diferentes mecanismos de acción en comparación con la this compound.
Singularidad de la this compound: El mecanismo de acción único de la this compound, el desarrollo lento de la resistencia y su importancia histórica como uno de los primeros compuestos químicos utilizados para tratar una enfermedad infecciosa destacan su importancia. A diferencia de los antimaláricos sintéticos, la this compound se deriva de una fuente natural y tiene una gama más amplia de aplicaciones .
Aplicaciones Científicas De Investigación
La quinina tiene una amplia gama de aplicaciones en la investigación científica:
Química: Sirve como un catalizador quiral en la síntesis asimétrica.
Biología: La this compound se utiliza para estudiar los efectos de los alcaloides en los sistemas biológicos.
Análisis Bioquímico
Biochemical Properties
Quinine plays a role in biochemical reactions as an electron carrier . It has the potential to bind to thiol, amine, and hydroxyl groups . These properties make quinine a biologically active compound .
Cellular Effects
Quinine is used to treat life-threatening infections caused by chloroquine-resistant Plasmodium falciparum malaria . It acts as a blood schizonticide and also has gametocytocidal activity against P. vivax and P. malariae . As a weak base, it is concentrated in the food vacuoles of P. falciparum .
Molecular Mechanism
It is known that quinine interferes with the parasite’s ability to break down and digest hemoglobin . Consequently, the parasite is poisoned by its own waste product (hemozoin) .
Temporal Effects in Laboratory Settings
It is known that quinine is a stable compound and can be used for quantitative analysis in liquids .
Dosage Effects in Animal Models
It is known that quinine has a narrow therapeutic index, with a large number of side effects at higher doses .
Metabolic Pathways
Quinine is metabolized in the liver by the cytochrome P450 system into several metabolites that are excreted in the urine
Transport and Distribution
Quinine is rapidly absorbed from the gastrointestinal tract and distributed throughout the body tissues . It is also known to cross the placenta and can be found in the fetus .
Subcellular Localization
Due to its weak base properties, it is known to accumulate in acidic compartments of the cell, such as food vacuoles of the malaria parasite .
Métodos De Preparación
Rutas sintéticas y condiciones de reacción: La síntesis total de la quinina ha sido un hito significativo en la química orgánica. La primera síntesis total estereoespecífica la logró Gilbert Stork en 2001. La ruta sintética implica múltiples pasos, incluida la formación de quinotoxina, que luego se convierte en this compound a través de una serie de reacciones .
Métodos de producción industrial: La producción industrial de this compound implica principalmente la extracción de la corteza del árbol de quina. La corteza se cosecha, se seca y luego se somete a una serie de procesos de extracción y purificación para aislar la this compound. La this compound extraída se convierte luego en varias sales, como sulfato de this compound o clorhidrato de this compound, para su uso medicinal .
Análisis De Reacciones Químicas
Tipos de reacciones: La quinina sufre varias reacciones químicas, incluyendo oxidación, reducción y sustitución. Por ejemplo, puede oxidarse para formar quinotoxina, que puede someterse a una reducción adicional para regenerar la this compound .
Reactivos y condiciones comunes:
Oxidación: Reactivos como el hipobromito de sodio se utilizan para la oxidación de la this compound a quinotoxina.
Principales productos: Los principales productos formados a partir de estas reacciones incluyen la quinotoxina y otros derivados, dependiendo de las condiciones de reacción y los reactivos específicos utilizados .
Comparación Con Compuestos Similares
Chloroquine: Another antimalarial drug that is more effective in suppressing the growth of blood forms of the malaria parasite.
Artemether and Lumefantrine: These are used in combination therapies for malaria and have different mechanisms of action compared to quinine.
Uniqueness of Quinine: Quinine’s unique mechanism of action, slow development of resistance, and its historical significance as one of the first chemical compounds used to treat an infectious disease highlight its importance. Unlike synthetic antimalarials, quinine is derived from a natural source and has a broader range of applications .
Propiedades
IUPAC Name |
(R)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/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/t13-,14-,19-,20+/m0/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
LOUPRKONTZGTKE-WZBLMQSHSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
COC1=CC2=C(C=CN=C2C=C1)C(C3CC4CCN3CC4C=C)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
COC1=CC2=C(C=CN=C2C=C1)[C@H]([C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C20H24N2O2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID0044280 |
Source
|
| Record name | Quinine | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID0044280 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
324.4 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Physical Description |
Solid |
Source
|
| Record name | Quinine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014611 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Solubility |
In water, 500 mg/L at 15 °C, 1 g dissolves in: 1900 mL water, 760 mL boiling water, 1 g dissolves in: 80 mL benzene (18 mL at 50 °C), 1.2 mL chloroform, 250 mL dry ether, 20 mL glycerol, 0.8 mL alcohol, 1900 mL of 10% ammonia water; almost insoluble in petroleum ether, Soluble in ether, chloroform, carbon disulfide, glycerol, alkalies, and acids (with formation of salts), Sol in pyrimidine, 3.34e-01 g/L |
Source
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| Record name | Quinine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00468 | |
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| Record name | QUININE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2501 | |
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| Record name | Quinine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014611 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Mechanism of Action |
The theorized mechanism of action for quinine and related anti-malarial drugs is that these drugs are toxic to the malaria parasite. Specifically, the drugs interfere with the parasite's ability to break down and digest hemoglobin. Consequently, the parasite starves and/or builds up toxic levels of partially degraded hemoglobin in itself., Quinine has a local anesthetic action and analgesic, antipyretic, and oxytocic effects. Quinine also has cardiovascular effects similar to those of quinidine. |
Source
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| Record name | Quinine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00468 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
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| Record name | QUININE | |
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Color/Form |
Triboluminescent, orthorhombic needles from absolute alcohol, Bulky, white, amorphous powder or crystalline alkaloid, CRYSTALS TURN BROWN ON EXPOSURE TO AIR | |
CAS No. |
72402-53-0, 130-95-0, 1407-83-6 |
Source
|
| Record name | (8α,9R)-(±)-6′-Methoxycinchonan-9-ol | |
| Source | CAS Common Chemistry | |
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| Record name | Quinine | |
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| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
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| Record name | Quinine [BAN:NF] | |
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| Record name | Quinine tannate [USP] | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0001407836 | |
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| Record name | Quinine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00468 | |
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| Record name | Cinchonan-9-ol, 6'-methoxy-, (8.alpha.,9R)- | |
| Source | EPA Chemicals under the TSCA | |
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| Record name | Quinine | |
| Source | EPA DSSTox | |
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| Record name | Quinine | |
| Source | European Chemicals Agency (ECHA) | |
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| Record name | QUININE | |
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| Record name | QUININE | |
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| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2501 | |
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| Record name | Quinine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014611 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Melting Point |
177 °C (some decomposition), Microcrystalline powder; mp: 57 °C; efflorescent; loses one water molecule in air, two water molecules over sulfuric acid; anhydrous at 125 °C /Quinine trihydrate/, 57 °C |
Source
|
| Record name | Quinine | |
| Source | DrugBank | |
| URL | https://www.drugbank.ca/drugs/DB00468 | |
| Description | The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information. | |
| Explanation | Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode) | |
| Record name | QUININE | |
| Source | Hazardous Substances Data Bank (HSDB) | |
| URL | https://pubchem.ncbi.nlm.nih.gov/source/hsdb/2501 | |
| Description | The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel. | |
| Record name | Quinine | |
| Source | Human Metabolome Database (HMDB) | |
| URL | http://www.hmdb.ca/metabolites/HMDB0014611 | |
| Description | The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body. | |
| Explanation | HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications. | |
Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
Q1: What is the primary mechanism of action of quinine against malaria?
A1: While the precise mechanism remains incompletely understood, quinine is known to exert its antimalarial effects by interfering with the parasite's ability to metabolize and detoxify heme. [] During its lifecycle within red blood cells, Plasmodium falciparum degrades hemoglobin, releasing toxic heme. Quinine accumulates in the parasite's digestive vacuole, forming complexes with heme and preventing its detoxification into hemozoin. This leads to a buildup of toxic heme, ultimately killing the parasite. []
Q2: How does quinine affect muscle cramps?
A2: The mechanism by which quinine relieves muscle cramps is not fully elucidated. Research suggests that it might interfere with the excitability of muscle fibers, reducing their tendency to contract involuntarily and cause cramps. [] Studies have shown that quinine can block acetylcholine-evoked responses in human muscle nicotinic acetylcholine receptors (nAChRs), suggesting a potential mechanism for its anti-cramping effects. []
Q3: Does quinine affect tryptophan levels in cells?
A3: Yes, research indicates that quinine can disrupt tryptophan transport within cells. It inhibits the uptake of tryptophan by associating with the high-affinity tryptophan/tyrosine permease, Tat2p. This association is suppressible by tryptophan, indicating a competitive interaction. The inhibition of tryptophan uptake by quinine can lead to tryptophan starvation in cells. []
Q4: What is the molecular formula and weight of quinine?
A4: The molecular formula of quinine is C20H24N2O2, and its molecular weight is 324.42 g/mol. []
Q5: Are there any spectroscopic techniques used to characterize quinine?
A5: Yes, various spectroscopic techniques, including Fourier transform infrared (FTIR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS), have been employed to characterize quinine and its derivatives. FTIR helps identify functional groups, while NMR provides insights into the molecule's structure and connectivity. MS confirms the molecular weight and fragmentation patterns, aiding in structural elucidation. [, , ]
Q6: Does quinine possess any catalytic properties?
A6: While not traditionally considered a catalyst, quinine and its derivatives have found applications in asymmetric synthesis as chiral ligands or organocatalysts. Their unique structural features, characterized by multiple chiral centers and a tertiary amine, enable them to influence the stereochemical outcome of reactions. [, ]
Q7: Have there been any computational studies conducted on quinine?
A7: Yes, computational chemistry approaches have been employed to study quinine's interactions with biological targets and to develop quantitative structure-activity relationship (QSAR) models. Molecular docking studies have provided insights into the binding modes of quinine with enzymes and receptors, while QSAR models have helped predict the antimalarial activity of quinine analogs based on their structural features. []
Q8: How do modifications to the quinine structure impact its activity?
A8: SAR studies have revealed that specific structural features are crucial for quinine's activity. The stereochemistry at the C-9 position significantly influences antimalarial potency, with quinine and quinidine exhibiting higher activity than their 9-epi counterparts. Modifications to the quinoline and quinuclidine rings, as well as the hydroxyl group, have also been explored to understand their impact on antimalarial activity, toxicity, and physicochemical properties. [, ]
Q9: How is quinine metabolized in the body?
A9: Quinine is primarily metabolized in the liver via oxidative pathways, involving cytochrome P450 enzymes. Major metabolites include 3-hydroxyquinine and 10,11-dihydroxydihydroquinine. The metabolic profile of quinine can be influenced by factors like genetic polymorphisms in drug-metabolizing enzymes, co-administration of other drugs, and liver function. [, ]
Q10: How does renal function affect quinine elimination?
A10: Renal impairment can significantly impact the elimination of quinine, as it is primarily excreted in the urine. In patients with chronic renal failure, particularly those on hemodialysis, the clearance of free (unbound) quinine is increased, leading to lower plasma concentrations. This altered pharmacokinetic profile necessitates careful dose adjustments to avoid toxicity. []
Q11: What types of in vitro and in vivo models are used to study quinine's activity?
A11: In vitro studies often utilize cultures of Plasmodium falciparum to determine the drug's efficacy in inhibiting parasite growth. Animal models, such as mice infected with malaria, are used to evaluate in vivo efficacy, pharmacokinetic properties, and potential toxicity. Clinical trials in humans are essential for assessing the drug's safety and efficacy in treating malaria. [, ]
Q12: What are the mechanisms of resistance to quinine in malaria parasites?
A12: Resistance to quinine in Plasmodium falciparum is a complex phenomenon, often involving mutations in genes encoding proteins involved in drug transport or drug targets. Mutations in the Pfmdr1 gene, encoding a transmembrane protein involved in drug efflux, have been associated with decreased susceptibility to quinine. []
Q13: What are the potential adverse effects of quinine?
A13: While generally well-tolerated at therapeutic doses, quinine can cause a range of adverse effects, including gastrointestinal disturbances, tinnitus, headache, and visual disturbances. In rare cases, it can lead to serious complications such as hemolytic anemia, thrombocytopenia, and hypoglycemia. Careful monitoring for adverse events is essential, especially in patients with underlying medical conditions. [, , , , ]
Q14: Are there strategies to improve the delivery of quinine to specific targets?
A14: Researchers are exploring various drug delivery approaches to enhance the targeting and efficacy of antimalarial drugs like quinine. Nanoparticle-based delivery systems, for example, hold promise in improving drug solubility, bioavailability, and targeted delivery to infected red blood cells, potentially reducing toxicity and improving therapeutic outcomes. []
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