Hydroquinidine hydrochloride - 1476-98-8
Hydroquinidine hydrochloride
Catalog Number: BT-354222
CAS Number: 1476-98-8
Molecular Formula: C20H27ClN2O2
Molecular Weight: 362.9 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
Product Introduction
Description
Hydroquinidine hydrochloride is a medication used to treat heart rhythm disorders such as atrial fibrillation and ventricular tachycardia. It belongs to the class of antiarrhythmic drugs and is a stereoisomer of quinidine. Hydroquinidine hydrochloride is a white crystalline powder that is soluble in water and ethanol.
Properties
CAS Number
1476-98-8
Product Name
Hydroquinidine hydrochloride
IUPAC Name
(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrochloride
Molecular Formula
C20H27ClN2O2
Molecular Weight
362.9 g/mol
InChI
InChI=1S/C20H26N2O2.ClH/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;/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3;1H/t13-,14-,19+,20-;/m0./s1
InChI Key
MULXTQKDWYBJMO-VJAUXQICSA-N
SMILES
CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O.Cl
Synonyms
dihydroquinidine
dihydroquinine
hydroquinidine
hydroquinidine dihydrochloride, (1beta,4beta,3S)-(+-)-isomer
hydroquinidine dihydrochloride, (3alpha,9S)-(+-)-isomer
hydroquinidine hydrochloride
hydroquinidine monosulfate
hydroquinidine monosulfate, (1beta,3alpha,4beta,8alpha,9R)-isomer
hydroquinidine monosulfate, (1beta,3alpha,4beta,9S)-isomer
hydroquinidine sulfate
hydroquinidine sulfate, (9S)-isomer
hydroquinidine, (+-)-isomer
hydroquinidine, (1beta, 3alpha,4beta,8alpha,9R)-isomer
hydroquinidine, (1beta,3alpha,4beta,9S)-isomer
hydroquinidine, (1beta,4beta,9S)-(+-)-isomer
hydroquinidine, (3alpha,9S)-(+-)-isomer
hydroquinidine, (8alpha,9R)-isomer
hydroquinidine, (8alpha,9S)-isomer
hydroquinidine, (9R)-isomer
hydroquinidine, (9S)-(+-)-isomer
hydroquinine
LCN 834
LCN-834
Lentoquine
Séréco
Canonical SMILES
CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O.Cl
Isomeric SMILES
CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)O.Cl
Method of Synthesis or Extraction
Hydroquinidine hydrochloride can be synthesized by several methods, including the reduction of quinidine with sodium borohydride, the reduction of quinidine with lithium aluminum hydride, and the reduction of quinidine with hydrogen gas over a palladium catalyst. The efficiency and yield of each method vary, with the reduction of quinidine with sodium borohydride being the most efficient and yielding the highest amount of hydroquinidine hydrochloride. However, this method requires the use of a large amount of sodium borohydride, which can be expensive and hazardous to the environment. The reduction of quinidine with lithium aluminum hydride is less efficient but produces a higher yield of hydroquinidine hydrochloride. This method also requires the use of a large amount of lithium aluminum hydride, which can be expensive and hazardous to the environment. The reduction of quinidine with hydrogen gas over a palladium catalyst is the least efficient and yields the lowest amount of hydroquinidine hydrochloride. However, this method is the most environmentally friendly and does not require the use of hazardous reagents.
Chemical Structure and Biological Activity
Hydroquinidine hydrochloride has a chemical formula of C20H26N2O2Cl and a molecular weight of 378.89 g/mol. It is a stereoisomer of quinidine and has a similar chemical structure. Hydroquinidine hydrochloride acts by blocking the potassium channels in the heart, which prolongs the action potential and slows down the heart rate. It also has a weak sodium channel blocking effect. Hydroquinidine hydrochloride has been shown to be effective in treating atrial fibrillation and ventricular tachycardia.
Biological Effects
Hydroquinidine hydrochloride has several biological effects on cell function and signal transduction. It blocks the potassium channels in the heart, which prolongs the action potential and slows down the heart rate. It also has a weak sodium channel blocking effect. Hydroquinidine hydrochloride has potential therapeutic and toxic effects. It can be used to treat heart rhythm disorders such as atrial fibrillation and ventricular tachycardia. However, it can also cause side effects such as nausea, vomiting, diarrhea, and dizziness. In rare cases, it can cause serious side effects such as arrhythmias, seizures, and allergic reactions.
Applications
Hydroquinidine hydrochloride has several applications in medical research, environmental research, and industrial research. In medical research, it is used in drug development to treat heart rhythm disorders such as atrial fibrillation and ventricular tachycardia. It has been tested in clinical trials and has been found to be effective in treating these disorders. However, it also has potential side effects that need to be carefully monitored. In environmental research, hydroquinidine hydrochloride has been studied for its effects on ecosystems and its role in pollution management. It has been found to have a low environmental impact and is not considered to be a major pollutant. In industrial research, hydroquinidine hydrochloride is used in manufacturing processes to improve product quality and efficiency. Health and safety considerations need to be taken into account when using hydroquinidine hydrochloride in industrial settings.
Future Perspectives and Challenges
The current limitations in the use and study of hydroquinidine hydrochloride include its potential side effects and the need for careful monitoring. Possible solutions and improvements include the development of new drugs with fewer side effects and the use of hydroquinidine hydrochloride in combination with other drugs to reduce its potential side effects. Future trends and prospects in the application of hydroquinidine hydrochloride in scientific research include the development of new drugs that target specific ion channels in the heart and the use of hydroquinidine hydrochloride in combination with other drugs to treat heart rhythm disorders. The challenges in the use and study of hydroquinidine hydrochloride include the need for more research on its potential side effects and the need for careful monitoring in clinical trials and industrial settings.
Conclusion:
Hydroquinidine hydrochloride is a medication used to treat heart rhythm disorders such as atrial fibrillation and ventricular tachycardia. It is synthesized by several methods, including the reduction of quinidine with sodium borohydride, the reduction of quinidine with lithium aluminum hydride, and the reduction of quinidine with hydrogen gas over a palladium catalyst. Hydroquinidine hydrochloride acts by blocking the potassium channels in the heart, which prolongs the action potential and slows down the heart rate. It has potential therapeutic and toxic effects and has several applications in medical research, environmental research, and industrial research. The current limitations in the use and study of hydroquinidine hydrochloride include its potential side effects and the need for careful monitoring. Possible solutions and improvements include the development of new drugs with fewer side effects and the use of hydroquinidine hydrochloride in combination with other drugs to reduce its potential side effects. Future trends and prospects in the application of hydroquinidine hydrochloride in scientific research include the development of new drugs that target specific ion channels in the heart and the use of hydroquinidine hydrochloride in combination with other drugs to treat heart rhythm disorders.
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