NMR Studies Of Drugs. Chiral Solvating Agents for Direct Determination of Enantiomeric Excess of the Cardiac Antiarrhythmic,Mexiletine |
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| Authors: | Hassan Y. Aboul-Enein Robert Rothchild Anton Sinnema |
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| Affiliation: | 1. Drug Development Laboratory , Radionuclide and Cyclotron Operations, King Faisal Specialist Hospital and Research Centre , P.O. Box 3354, Riyadh, 11211, Kingdom of Saudi Arabia;2. The City University of New York John Jay College of Criminal Justice, Science Department, Toxicology Research and Training Center , 445 West 59th Street, New York, NY, 10019-1199;3. Delft University of Technology, Faculty of Chemical Technology and Materials Science, Laboratory of Organic Chemistry and Catalysis , Julianalaan 136, 2628, BL Delft, The Netherlands |
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| Abstract: | The 400 MHz 1H NMR spectra of the cardiac antiarrhythmic, mexiletine, 1, have been studied with different chiral solvating agents (CSA) to obtain a very promising method for direct determination of enantiomeric excess (e.e.) with limited amounts of 1. The methods included the use of β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), α-methoxy-α-(trifluoromethyl)phenylacetic acid (MTPA), and 2,2,2-trifluoro-1-(9-anthryl)ethanol (TFAE). Use of TFAE in CDCl3 with the free base of 1 appeared to give the best results, with enantiomeric shift differences observed for the signals of the sidechain methyl, CH 3CH, and the aryl methyls. |
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| Keywords: | Optical Purity Enantiomer Analysis 1-(2,6-Dimethylphenoxy)-2-propanamine Antiarrhythmic Cyclodextrin α-Methoxy-α-(trifluoromethyl)phenylacetic acid MTPA 2,2,2-Trifluoro-1-(9-anthryl)ethanol TFAE |
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