title: GC-MS analysis of acylated derivatives of the side chain and ring regioisomers of methylenedioxymethamphetamine.
abstract: 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.
authors.affiliation: Department of Pharmacal Sciences, School of Pharmacy, Auburn University, Auburn, AL 36849, USA.
authors.forename: Tamer
authors.initials: T
authors.lastname: Awad
authors.forename: Jack
authors.initials: J
authors.lastname: DeRuiter
authors.forename: C Randall
authors.initials: CR
authors.lastname: Clark
mesh_terms: 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
chemical_list: D007202:Indicators and Reagents; D018817:N-Methyl-3,4-methylenedioxyamphetamine