P. Castelnovo, DETERMINATION OF THE ENANTIOMERIC PURITY OF 5,6-DIHYDROXY-2-AMINOTETRALINS AND 6,7-DIHYDROXY-2-AMINOTETRALINS BY CHIRAL HPLC, Chirality, 5(3), 1993, pp. 181-187
5,6- and 6,7-Dihydroxy-2-aminotetralin (ADTN), racemic dopamine recept
or agonists, were resolved into their enantiomers by a new chiral HPLC
assay. The separation was performed on a Crownpack CR column, which c
ontains an 18-crown-6-type chiral crown ether as a chiral selector. Th
e chiral recognition is based on the complexation of the protonated pr
imary 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 f
or 5,6-ADTN and 1.1 for 6,7-ADTN resulting in very low limits of quant
itation (<0.1%) of the enantiomer present as impurity. Data on the val
idation of the assay and on the stability of the column are also repor
ted.