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Abstract
In recent years, a large number of clandestinely synthesized new psychoactive substances with high structural variety have been detected in forensic samples. Analytical differentiation of regioisomers is a significant issue in forensic drug analysis, because, in most cases, legal controls are placed on only one or two of the conceivable isomers. In this study, gas chromatography–tandem mass spectrometry (GC–MS–MS) was used to differentiate the regioisomers of chloroamphetamine analogs (chloroamphetamines and chloromethamphetamines) synthesized in the authors′ laboratories. Free bases, trifluoroacetyl derivatives, and trimethylsilyl derivatives were subjected to GC–MS–MS using DB-1ms, DB-5ms, and DB-17ms capillary columns, respectively. The regioisomers of chloroamphetamine analogs in all forms were well separated on the DB-5ms column. The electron ionization mass spectra of the chloroamphetamine analogs gave very little structural information for differentiation among these analogs, even after trifluoroacetyl and trimethylsilyl derivatization of the analytes. Characteristic product ions of the 2-positional isomers were observed by electron ionization-MS–MS. In contrast, chemical ionization-MS–MS of the free bases provided more structural information about chloride position on the aromatic ring when [M+H–HCl]+ was selected as a precursor ion. The results suggest that a combination of chromatographic analysis and MS–MS supports differentiation for regioisomers of chloroamphetamine analogs.
Highlights
In recent years, a large number of controlled substance analogs with high structural variety have been widely distributed as noncontrolled alternatives and have been detected in forensic samples
In recent years, a large number of clandestinely synthesized new psychoactive substances with high structural variety have been detected in forensic samples
Trifluoroacetyl derivatives, and trimethylsilyl derivatives were subjected to Gas chromatography–mass spectrometry (GC–MS)–MS using DB-1ms, DB-5ms, and DB-17ms capillary columns, respectively
Summary
A large number of controlled substance analogs with high structural variety have been widely distributed as noncontrolled alternatives and have been detected in forensic samples. Because of the frequent appearance of new analogs with displacement of a functional group or an alkyl chain [1–3], structural differentiation of these new drugs is necessary in forensic laboratories for legal control against drug abuse [4–14]. It was eventually concluded that these analogs were not clinically useful and produced less central-nervous system stimulation than amphetamine or methamphetamine. After these reports were published, many researchers studied chloroamphetamines (CAPs) as factors of selective serotonin (5-hydroxytriptamine, 5-HT) diminution and as monoamine oxidase (MAO) inhibitors in brain nerve terminals [18–20]. There have been no reports of chloroamphetamine analogs (CAPs and CMAs) being abused and detected in forensic samples in Japan, 4-CAP has been controlled as a designated substance since August 2014. Gas chromatography–mass spectrometry (GC–MS) is generally used for the identification of drugs because it is
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