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Zaitsu K, Katagi M, Hiroe H, Nakanishi K, Shima N, Kamata T, Nishioka H, Miki A, Tatsuno M and Tsuchihashi H. 
“Simultaneous analysis of six novel hallucinogenic tetrahydrobenzodifuranylaminoalkanes FLYs and benzodifuranylaminoalkanes DragonFLYs by GC-MS, LC-MS, and LC-MS-MS”. 
Forensic Toxicol. 2010 Jan 1;28(1):9-18.
Six novel hallucinogens classed as tetrahydrobenzodifuranyl aminoalkanes or benzodifuranylaminoalkanes, which are known by the common names of “FLY” and “DragonFLY,” respectively, were synthesized. These compounds were simultaneously analyzed by gas chromatography GC-mass spectrometry MS, liquid chromatography LC-MS, and LC-MS-MS. GCMS analysis of their free bases was not satisfactory for both mass spectral and chromatographic measurements, and thus trifluoroacetyl TFA derivatization was employed. However, it was found that the usual TFA derivatization procedure using trifluoroacetic anhydride caused dehydrogenation of FLYs to the corresponding DragonFLYs. Therefore, TFA derivatization of FLYs was reinvestigated the presence of triethylamine could almost inhibit such dehydrogenation. LC separation of the analytes was successfully achieved by using a phenyl-type semimicro column with methanol gradient elution, while 1-8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b4,5-b&8242]difuran-4-yl-2-methylaminopropane N-methyl-DOB-FLY and 1-8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b4,5-b&8242]difuran-4-yl-2-aminopropane DOB-FLY were not separated on an octadecylsilica ODS-type column. Specific product ion spectra for all compounds were also obtained using LC-MS-MS, which enabled sensitive and reliable identification.
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