Simultaneous analysis of six novel hallucinogenic (tetrahydrobenzodifuranyl)aminoalkanes (FLYs) and (benzodifuranyl)aminoalkanes (DragonFLYs) by GC-MS, LC-MS, and LC-MS-MS
Six novel hallucinogens classed as (tetrahydrobenzodifuranyl) aminoalkanes or (benzodifuranyl)aminoalkanes, 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-b;4,5-b′]difuran-4-yl)-2-methylaminopropane (N-methyl-DOB-FLY) and 1-(8-bromo-2,3,6,7-tetrahydrobenzo[1,2-b;4,5-b′]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.
Keywords(Tetrahydrobenzodifuranyl)aminoalkanes (Benzodifuranyl)aminoalkanes FLY DragonFLY Hallucinogen MS analysis
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- 4.Reed EC, Kiddon GS (2007) The characterization of three FLY compounds (2C-B-FLY, 3C-B-FLY, and Bromo-DragonFLY). Microgram J 5:26–33Google Scholar
- 5.Anonymous (2007) “Bromo dragonfly” (bromo-benzodifuranyl-isopropylamine) in Ashland, Oregon. Microgram Bull 40:78Google Scholar
- 6.Anonymous (2008) “Bromo-Dragonfly” in Queensland, Australia. Microgram Bull 41:16–17Google Scholar
- 7.Erowid (2009) The vaults of Erowid. http://www.erowid.org/chemicals/bromo_dragonfly/bromo_dragonfly.shtml. Cited August 2009
- 13.Kovats ES (1965) Gas chromatographic characterization of organic substances in the retention index system. Adv Chromatogr 1:229–247Google Scholar
- 15.McLafferty FW, Turecek F (1993) Interpretation of mass spectra, 4th edn. University Science, Mill Valley, CAGoogle Scholar
- 16.Smith RM, Busch KL (1999) Understanding mass spectra—a basic approach. Wiley, New YorkGoogle Scholar
- 17.Katagi M, Tsutsumi H, Miki A, Nakajima K, Tsuchihashi H (2002) Analyses of clandestine tablets of amphetamine and their related designer drugs encountered in recent Japan. Jpn J Forensic Toxicol 20:303–319Google Scholar
- 22.Patai S (1974) The chemistry of the quinonoid compounds. Wiley, New YorkGoogle Scholar
- 24.Kamata HT, Shima N, Zaitsu K, Kamata T, Nishikawa M, Katagi M, Miki A, Tsuchihashi H (2007) Simultaneous analysis of new designer drug, methylone, and its metabolites in urine by gas chromatography-mass spectrometry and liquid chromatography-electrospray ionization mass spectrometry. Jpn J Forensic Sci Technol 12:97–106CrossRefGoogle Scholar
- 25.Shima N, Katagi M, Kamata H, Zaitsu K, Kamata T, Miki A, Tsuchihashi H, Sakuma T, Nemoto N (2008) Conjugates of p-hydroxymethamphetamine and 4-hydroxy-3-methoxymethamphetamine in blood obtained from methamphetamine and 3,4-methylendioxymethamphetamine users: analysis by LC-MS-MS. Forensic Toxicol 26:58–65CrossRefGoogle Scholar
- 28.Decaestecjer T, De Letter E, Clauwaert K, Bouche MP, Lambert W, Van Bocxlaer J, Piette M, Van den Eeckhout E, Van Peteghem C, De Leenheer A (2001) Fatal 4-MTA intoxication: development of a liquid chromatographic-tandem mass spectrometric assay for multiple matrices. J Anal Toxicol 25:705–710Google Scholar