Resolution of Racemic Propranolol in Liquid Membranes Containing TA‐β‐cyclodextrin

Abstract

The pharmacological properties of propranolol enantiomers are quite different, the β‐adrenergic blocking activity resides in the (S)‐(−) isomer, while the (R)‐(+)‐enantiomer has only a membrane stabilizing effect. The inherent chirality of cyclodextrins (CDs) allows them to form diastereomeric complexes. In this work, a peracetylated β‐CD (TA‐β‐CD) that preferentially interacts with the (S)‐(−) isomer of propranolol was used. Two liquid membranes, bulk liquid membrane (BLM) and supported liquid membrane (SLM) were tested. A recovery of 30% and a enantiomeric excess of 12% were obtained, using a SLM with 10 mM of propranolol and a pH gradient between feed and stripping phases.

Keywords:

• Propranolol
• cyclodextrins
• liquid membranes
• racemic resolution

Acknowledgements

This work has been supported by “Fundação para a Ciência e Tecnologia” through project POCTI/FCB/43942/2001.