NMR-STUDIES OF DRUGS - APPLICATIONS OF ACHIRAL AND CHIRAL LANTHANIDE SHIFT-REAGENTS TO THE ANALGESIC, FAMPROFAZONE - ANOMALOUS SHIFTS

The 200 MHz H-1 NMR spectra of the analgesic, famprofazone, 1, have be en studied in CDCl3 solution at ambient temperatures with the achiral lanthanide shift reagent (LSR) uoro-2,2-dimethyl-3,5-octanedionato)eur opium(III), Eu(FOD)(3), 2, for spectral simplification, and with the c hiral LSR, pylhydroxymethylene)-(+)-camphorato]europium(III), Eu(HFC)( 3), 3. Lanthanide induced shift (LIS) magnitudes suggested predominant LSR binding at the carbonyl oxygen. Substantial enantiomeric shift di fferences were observed far several nuclei of 1 with added 3 which cou ld permit direct determinations of enantiomeric excess.