Absolute Configuration of (+)-Erythro-Mefloquine

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  • Author: ChemPlusChem
  • Published Date: 28 June 2013
  • Source / Publisher: ChemPlusChem/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Absolute Configuration of (+)-Erythro-Mefloquine

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Mefloquine (MQ), a known antimalarial drug, is commercially available as a racemate where both enantiomers have been shown to display biological differences. The (+)-MQ is more active on some Plasmodium strains, whereas the (–)-MQ is known to act as an adenosine receptor agonist; such binding is believed to be responsible for neuropsychiatric side effects such as depression and psychosis.

A number of researchers have attempted to determine the absolute configuration of erythro-mefloquine enantiomers in the past. Uwe M. Reinscheid and Christian Griesinger, Max-Planck-Institut für Biophysikalische Chemie, Göttingen, Germany, Birger Dittrich, Georg-August-Universität Göttingen, Germany, and co-workers have determined the X-ray crystal structures two mefloquine enantiomeric Mosher amides. Meanwhile, Pascal Sonnet, Université de Picardie Jules Verne, Amiens cedex, France, and colleagues reported the X-ray crystallography, CD spectroscopy, and molecular modelling of both MQ enantiomers along with their respective antimalarial activities.

In these two publications, the absolute configuration of (+)-erythro-mefloquine has been determined as (11S, 12R).

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