Metabolic fate, mass spectral fragmentation, detectability, and differentiation in urine of the benzofuran designer drugs 6-APB and 6-MAPB in comparison to their 5-isomers using GC-MS and LC-(HR)-MSn techniques

Abstract

Metabolic fate, mass spectral fragmentation, detectability, and differentiation in urine of the benzofuran designer drugs 6-APB and 6-MAPB in comparison to their 5-isomers using GC-MS and LC-(HR)-MSn techniques

Combined in vitro and in silico approaches to the assessment of stimulant properties of novel psychoactive substances – The case of the benzofuran 5-MAPB

“…For the present study, we have chosen 1-(1-benzofuran-5-yl)-N-methylpropan-2-amine (5-MAPB) which is a N-methylated version of 5-APB, structurally related to MDMA (Welter et al, 2015a(Welter et al, , 2015b. Online drug user fora suggest that 5-MAPB, despite its illegality, is still being used today.…”

Differentiation of 2- and 6-isomers of (2-dimethylaminopropyl)benzofuran by tandem mass spectrometry

“…1) два изомера, 5-(2-аминопропил)бен-зофуран (5-APB) и 6-(2-аминопро-пил)бензофуран (6-APB), а также их N-метильные производные (5-MAPB и 6-MAPB, соответственно). Соеди-нения 5-АРВ и 6-АРВ являются анта-гонистами серотониновых рецепто-ров и по своему фармакологическому действию подобны стимуляторам ам-фетаминового ряда [3,4]. На террито-рии России оборот 5-АРВ, 6-АРВ и их N-метильных производных контроли-руется законодательством.…”

“…The probable structure of the major fragment ions in the CID spectra of the compounds 2-MAPB and 6-MAPB значений параметров хроматографи-ческого удерживания этих соединений (рис. 2), а также их ацильных произ-водных [3,4]. Осенью 2015 года в нелегальном обороте нами впервые было обна-ружено еще одно соединение, изо-мерное 5-MAPB и 6-MAPB, а именно 2-(2-метиламинопропил)бензофуран (2-МAPB), структура которого была достоверно установлена с использо-ванием масс-спектрометрии высокого разрешения и двумерной ЯМР-спек-троскопии.…”

“…6-APB are serotonin receptor agonists and their pharmacological effects are similar to amphetamine-type stimulants [3,4]. In the territory of the Russia the circulation of 5-APB, 6-APB and these N-methyl derivatives is controlled by legislation.…”

“…When conducting analysis by gas chromatography-mass spectrometry using typical gas chromatography columns for drug identification with dimethylpolysiloxane nonpolar stationary phase (such as HP-5) the differentiation of compounds 5-APB and 6-APB or 5-MAPB and 6-MAPB is possible due to the differences in the values of parameters of the chromatographic retention of these compounds (Fig. 2) or their acyl derivatives [3,4].…”