Identification of (2‐aminopropyl)benzofuran (APB) phenyl ring positional isomers in Internet purchased products

Abstract

5-(2-Aminopropyl)benzofuran (5-APB), a 'research chemical' that was first reported by UK authorities to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) in 2010, is anecdotally reported to produce a combination of stimulant and entactogenic effects. More recently, in 2011, 6-(2-aminopropyl)benzofuran (6-APB) was identified by Hungarian authorities. To confirm positional isomer identity in Internet purchased products, 4- 5- 6- and 7-APBs were synthesized and found to be separable by gas chromatography (as heptafluorobutyramide derivatives) and liquid chromatography. The analyses of products purchased from online vendors of 'research chemicals' identified the presence of 5- or 6-APBs. These findings were further confirmed by liquid chromatography-mass spectrometry and (1) H nuclear magnetic resonance spectroscopy. In products containing 6-APB, the 4- positional isomer was also identified and this may have arisen during the manufacturing process.

Benzofuran analogues of amphetamine and methamphetamine: studies on the metabolism and toxicological analysis of 5-APB and 5-MAPB in urine and plasma using GC-MS and LC-(HR)-MSn techniques

“…Chemicals and reagents 5-APB and 5-MAPB were synthesized [4] and provided by the Department of Pharmacology and Therapeutics, Trinity Centre for Health Sciences, St. James's Hospital (Dublin, Ireland), before scheduling. Isolute C18 (500 mg, 3 mL) and HCX cartridges (130 mg, 3 mL) were obtained from Biotage (Uppsala, Sweden); MDMA and MDMA-d 5 from LGC (Wesel, Germany); isocitrate and isocitrate dehydrogenase, heptafluorobutyric anhydride, and sodium phosphate from Sigma-Aldrich (Taufkirchen, Germany); NADP + from Biomol (Hamburg, Germany); acetonitrile (LC-MS grade), ammonium formate (analytical grade), formic acid (LC-MS grade), methanol (LC-MS grade), and mixture (100,000 Fishman units/mL) of glucuronidase (EC No.…”

“…The fragmentation patterns of other amphetamines or benzofurans [4,11] and the general fragmentation rules described by, e.g., Smith and Bush or McLafferty were taken into consideration [19,20]. Furthermore, the metabolism of other furan or benzofuran containing compounds was considered [21][22][23][24][25][26][27].…”

“…Stanczuk et al investigated the differentiation of the positional isomers of APB in purchased products. They could separate them by gas chromatographymass spectrometry (GC-MS) after heptafluorobutyrylation [4]. Casale et al also differentiated between the several positional isomers by GC-MS but without derivatization [5].…”

Re: Nye rusmidler rett fra nett

“…A positional analysis of the side chain of both compounds purchased from internet sites has recently been published by Stanczuk et al, (2013).…”

The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat

“…5-and 6-APB are structural isomers and were first developed in the early 1990s (Monte et al, 1993). There has been difficulty in separating the 5-and 6-APB isomers, and perhaps the occurrence of the 4-APB isomer, but chemical analysis can now differentiate these isomers (Stanczuk et al, 2013). Anecdotal user reports suggest that benzofury has entactogenic and stimulant effects and that 5-APB is more potent than 6-APB.…”