Several synthetic cannabinoids such as AM-2201 contain the 3-carbonyl-
N-fluoropentylindole structure. This structure has fluorine positional isomers on the alkyl chain. In most cases, legal controls are placed only on the 5-fluoro analogue. Thus, differentiation of isomers is a significant issue in forensic science. In this study, we developed a method for the differentiation of positional isomers of 3-carbonyl-
N-fluoropentylindole derivatives utilizing multiple-stage mass spectrometry using an ion trap tandem mass spectrometer. In addition, the analogues whose fluorine atom was replaced with a chlorine atom or hydroxyl group were also examined.
With respect to each positional isomer of fluorine and chlorine, the ion at
m/z 232 or
m/z 248, obtained by MS
2 analysis of [M+H]
+, were selected as the precursor ions for MS
3 analysis. The ion at
m/z 232 and
m/z 248 corresponded to the 3-carbonyl-
N-fluoropentylindole and 3-carbonyl-
N-chloropentylindole structures. Furthermore, the ion at
m/z 212, corresponding to the de-halogenated fragments of the 3-carbonyl-
N-fluoropentylindole- and 3-carbonyl-
N-chloropentylindole-structures, was selected as the precursor ion for MS
4 analysis. Consequently, combination of these MS
n analysis achieved differentiation of all the positional isomers.
With respect to positional isomers with the hydroxyl group, however, the fragment ion at
m/z 212 was not observed from the MS
3 analysis of
m/z 230, which corresponds to the 3-carbonyl-
N-fluoropentylindole structure. Therefore, differentiation of each positional isomer was not achieved by MS
n analysis.
This method is useful for the differentiation of positional isomers of 3-carbonyl-
N-fluoropentylindole and 3-carbonyl-
N-chloropentylindole derivatives.
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