Determination of the enantiomeric purity of 5,6‐ and 6,7‐dihydroxy‐2‐aminotetralins by chiral HPLC

Abstract

Abstract5,6‐ and 6,7‐Dihydroxy‐2‐aminotetralin (ADTN), racemic dopamine receptor agonists, were resolved into their enantiomers by a new chiral HPLC assay. The separation was performed on a Crownpack CR column, which contains an 18‐crown‐6‐type chiral crown ether as a chiral selector. The chiral recognition is based on the compiexation of the protonated primary amino group and the oxygen atoms inside the cavity of the crown ether. The amino group is attached to the chiral centre and therefore these compounds could be resolved. Mobile phase was perchloric acid pH 2.0 and the detection was UV at 200 nm. Resolution factors were 3.1 for 5,6‐ADTN and 1.1 for 6,7‐ADTN resulting in very low limits of quantitation (<0.1%) of the enantiomer present as impurity. Data on the validation of the assay and on the stability of the column are also reported. © 1993 Wiley‐Liss, Inc.