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Disubstituted piperazine analogues of trifluoromethylphenylpiperazine and methylenedioxybenzylpiperazine: analytical differentiation and serotonin receptor binding studies

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Forensic Sciences Research 2018年第2期3卷 161-169页

作者： jack deruiter Ashleigh Van Cleave Audinei de Sousa Moura Younis Abiedalla C.Randall Clark Department of Drug Discovery and Development Harrison School of PharmacyAuburn UniversityAuburnALUSA Department of Pharmacy Federal University of PiauiTeresinaBrazil Faculty of Pharmacy Department of Medicinal ChemistryOmar Al-Mukhtar UniversityEl-BeidaLibya

A series of N,N-disubstituted piperazines were synthesized containing the structural elements of both methylenedioxybenzylpiperazine (MDBP) and trifluoromethylphenylpiperazine (TFMPP)in a single *** six potential designer drug molecules having a regioisomeric relationship were compared in gas chromatography-mass spectrometry (GC-MS),gas chromatography-infrared spectroscopy and serotonin receptor affinity *** compounds were separated by capillary gas chromatography on an Rxi(R)-17Sil MS stationary phase film and the elution order appears to be determined by the position of aromatic ring *** majority of electron ionization mass spectral fragment ions occur via processes initiated by one of the two nitrogen atoms of the piperazine *** major electron ionization mass spectrometry (El-MS) fragment ions observed in all six of these regioisomeric substances occur at m/z =364,229,163 and *** relative intensity of the various fragment ions is also equivalent in each of the six El-MS *** vapour phase infrared spectra provide a number of absorption bands to differentiate among the six individual compounds on this regioisomeric ***,the mass spectra place these compounds into a single group and the vapour phase infrared spectra differentiate among the six regioisomeric *** of the TFMPP-MDBP regioisomers displayed significant binding to 5-HT2B receptors and in contrast to 3-TFMPP,most of these TFMPP-MDBP isomers did not show significant binding at 5-HT1 receptor *** the 3-TFMPP-3,4-MDBP (Compound 5) isomer displayed affinity comparable to 3-TFMPP at 5-HT1A receptors (Ki =188 nmol/L).

关键词： Forensic science forensic toxicology gas chromatography-mass spectrometry gas chromatography-infrared spectroscopy regioisomers receptors serotonin disubstituted piperazines

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