GC-MS analysis of acylated derivatives of the side chain and ring regioisomers of methylenedioxymethamphetamine.
The perfluoroacyl derivatives (pentafluoropropionylamides and heptafluorobutrylamides) of the primary and secondary regioisomeric amines, related to the controlled drug substance 3,4-methylenedioxymethamphetamine, are prepared and evaluated in GC-MS studies. These derivatives show excellent resolution on nonpolar stationary phases, such as RTX-1 and RTX-5, with elution order differences from those of the underivatized amines. The mass spectra for these derivatives are significantly individualized, and the resulting unique fragment ions allow for specific side-chain identification. The individualization is the result of fragmentation of the alkyl carbon-nitrogen bond, yielding hydrocarbon fragments and other unique ions. The heptafluoro butrylamides derivatives offer more fragment ions for molecular individualization among these regioisomeric substances.
Awad
Tamer
T
Department of Pharmacal Sciences, School of Pharmacy, Auburn University, Auburn, AL 36849, USA.
DeRuiter
Jack
J
Clark
C Randall
CR
D000215:Acylation; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D007202:Indicators and Reagents / Q000737:chemistry; D018817:N-Methyl-3,4-methylenedioxyamphetamine / Q000032:analysis* / Q000737:chemistry; D013237:Stereoisomerism
D007202:Indicators and Reagents; D018817:N-Methyl-3,4-methylenedioxyamphetamine