1. Salmeterol Is a Component of the Top-Selling Asthma and COPD Drug Advair® racemic salmeterol bronchodialator fluticasone propionate anti-inflammatory $3.6 billion in U.S. sales in 2008 (top 5 drugs for sales) Marketed by Glaxo Smith Kline (GSK), Approved 2000

2. Salmeterol Is a Long-Acting Beta-Adrenoceptor Agonist Salmeterol Long-acting beta-adrenoceptor agonist (12 hour duration) Bronchodialation via relaxation of smooth muscle in airway Mechanism of action: Stimulation of adenyl cyclase, which converts ATP to cAMP, resulting in smooth muscle relaxation albuterol (Ventolin®, Proventil®) Short-acting beta-adrenoceptor agonist (4-6 hour duration)

3. (S)-salmeterol Reported as more selective enantiomer for  2 receptors and claimed to have fewer side effects (R)-salmeterol More potent enantiomer Salmeterol Enantiomers

4. Chiral NMR Shift Reagent (R)-2,2,2-trifluoro-1-(9-anthryl)ethanol Forms diasteromeric solvates with enantiomeric compounds via hydrogen bonding Chiral shift reagent forms diasteromeric solvates with enantiomers via hydrogen bonding

5. Example of a Chiral HPLC Trace (Not from Salmeterol Literature) Chiral HPLC column interacts differently with two enantiomers, resulting in different retention times

6. Detection Limits of Product Purity NMR Generally 95% HPLC Generally 98%