STEREOSPECIFIC DERIVATIZATION OF AMPHETAMINES, PHENOL ALKYLAMINES, AND HYDROXYAMINES AND QUANTIFICATION OF THE ENANTIOMERS BY CAPILLARY GLCMS/

The enantiomers of amphetamines, phenol alkylamines, and hydroxyamines are separated by using alpha-methoxy-alpha-(trifluoromethyl)phenylace tyl chloride as the chiral derivatizing agent for amino groups, Prior to N-acylation, amine salts are converted into the free bases and hydr oxyl groups into O-silyl ethers by reaction with N-methyl-N-silylamide s, N-Methyl-N-(trimethylsilyl)trifluoroacetamide, N-methyl-N-(triethyl silyl)trifluoroacetamide, or ethyl-N-(tert-butyldimethylsilyl)trifluor acetamide was used to protect the hydroxyl groups by TIMS, TES, or the tBDMS groups. All these N-methyl-N-silylamides were able to convert a mino salts to the free bases. The reaction is selective and rapid, and the diastereomeric derivatives are well separated by capillary gas-li quid chromatography, This procedure is suitable for simultaneous deter mination by gas chromatography/mass spectrometry with selected-ion mon itoring and is also applicable to quantification of the compounds in a biological matrix.