{"title":"Hydrogen-deuterium (H/D) exchange reaction of acebutolol hydrochloride in D₂O and CD₃OD solution.","authors":"H Guesmi, J Ben Kraim, A Alatrache, U Holzgrabe","doi":"10.1691/ph.2022.2419","DOIUrl":null,"url":null,"abstract":"<p><p>H/D exchange reactions can be observed by NMR spectroscopy of acebutolol (ACE). The results obtained showed deuterium incorporation at α-posi t ion of the carbonyl group of acebutolol, when using deuterium oxide or deuterated methanol as deuterium source and solvent. The spontaneous deuteration is proceeded by the following pathway CH₃→CH₂D→CHD→CD₃, through a keto-enol tautomerization reaction. Furthermore, LC-MS / QTOF analyses have confirmed the proposed H/D exchange. In order to reduce the time of total deuteration observed at the acetyl group alkaline catalysts were employed.</p>","PeriodicalId":20145,"journal":{"name":"Pharmazie","volume":"77 7","pages":"217-223"},"PeriodicalIF":1.5000,"publicationDate":"2022-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Pharmazie","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1691/ph.2022.2419","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 1
Abstract
H/D exchange reactions can be observed by NMR spectroscopy of acebutolol (ACE). The results obtained showed deuterium incorporation at α-posi t ion of the carbonyl group of acebutolol, when using deuterium oxide or deuterated methanol as deuterium source and solvent. The spontaneous deuteration is proceeded by the following pathway CH₃→CH₂D→CHD→CD₃, through a keto-enol tautomerization reaction. Furthermore, LC-MS / QTOF analyses have confirmed the proposed H/D exchange. In order to reduce the time of total deuteration observed at the acetyl group alkaline catalysts were employed.
期刊介绍：
The journal DiePharmazie publishs reviews, experimental studies, letters to the editor, as well as book reviews.
The following fields of pharmacy are covered:
Pharmaceutical and medicinal chemistry;
Pharmaceutical analysis and drug control;
Pharmaceutical technolgy;
Biopharmacy (biopharmaceutics, pharmacokinetics, biotransformation);
Experimental and clinical pharmacology;
Pharmaceutical biology (pharmacognosy);
Clinical pharmacy;
History of pharmacy.
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