Elucidation of the fluorine substitution position on the phenyl ring of synthetic cannabinoids by electron ionization-triple quadrupole mass spectrometry

• DOI: 10.3408/jafst.722
• Publication Date: 2017-04-27T22:09:04Z
• Authors: Takaya Murakami; Yoshiaki Iwamuro; Reiko Ishimaru; Satoshi Chinaka; Ippei Noda; Shuhei Higashibay...; Nariaki Takayama
• Keywords: Synthetic cannabinoids; Fluorine

We present herein a practical methodology for elucidating the o-, m-, or p-fluorine substitution pattern of indazole-type synthetic cannabinoids containing fluorobenzyl group at N-1 position and carbonyl C-3 via electron ionization-triple quadrupole mass spectrometry. synthesized, as model compounds cannabinoids, positional isomers: 1-[1-(2-, 3-, 4-fluorobenzyl)-1H-indazol-3-yl]ethanone (o-, p-FUBINAE). Mass spectral analyses showed that three isomers differed significantly in logarithmic values abundance ratios product ion m/z 109 to precursor 253 (ln(A109/A253)), following order meta<ortho<para. In addition, relationships between ln(A109/A253) collision energy were linear with high correlation coefficients. Comparing plots FUBINAE versus similar AB-FUBINACA its o- m-fluorobenzyl behaved did same fluorine on phenyl ring. Moreover, other p-fluorobenzyl (ADB-FUBINACA, FUB-AMB, FUB-APINACA, FUB-NPB-22, FU-PX-2) also exhibited behavior p-FUBINAE. These results indicated ring can be differentiated by collating according their function energy.