Enantiomeric composition analysis of amphetamine and methamphetamine by chiral phase high-performance liquid chromatography-mass spectrometry.
N-(Trifluoroacetyl)-l-prolyl- (N-TFA-l-prolyl-) d- and l-amphetamine diastereoisomers were separated by high-performance liquid chromatography and confirmed by an interfaced mass spectrometer system, using the commercially available N-3,5-(dinitrobenzoyl)phenylglycine chiral column. A separation factor of 1.52 and resolution of 3.8 were observed. N-TFA-l-prolyl-d- and -l-methamphetamine diastereoisomers were only partially resolved. The chiral stationary phase-solute interactions were studied by varying the mobile phase (2-propanol in hexane). Results indicate the separation mechanism proceeds via dipolar and hydrogen-bond interactions between the chiral stationary phase and the solute. A modified "dipole-stacking" model takes into account these interactions and explains the difference in separability observed for N-TFA-l-prolyl-d- and -l-amphetamine and N-TFA-l-prolyl-d- and -l-methamphetamine.
Hayes
S M
SM
Department of Criminal Justice, University of Alabama at Birmingham 35294.
Liu
R H
RH
Tsang
W S
WS
Legendre
M G
MG
Berni
R J
RJ
Pillion
D J
DJ
Barnes
S
S
Ho
M H
MH
D000661:Amphetamine / Q000032:analysis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D013058:Mass Spectrometry; D008694:Methamphetamine / Q000032:analysis*; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism
D007202:Indicators and Reagents; D008694:Methamphetamine; D000661:Amphetamine