The syntheses and characterization 3β‐(4‐fluorobenzoyloxy)tropane (fluorotropacocaine) and its 3α isomer

Abstract

3β-(4-Fluorobenzoyloxy)tropane (3β-FBT, fluorotropacocaine) was first reported by Finnish authorities to the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) via the Early Warning System (EWS) in 2008 and our own laboratory tentatively identified it in 2010 in several products purchased from head shops. Very little is known about this cocaine-like drug and, as no reference standards were available, we have synthesized and characterized both 3β-FBT and its 3α isomer for use as reference standards. The two compounds are separable by gas chromatography (GC) but their electron-impact (EI) mass spectra were found to be almost identical. ¹⁹F NMR spectroscopy was also found to be a useful technique for distinguishing the two isomers.

Contribution of human esterases to the metabolism of selected drugs of abuse

“…Fresh, pooled human blood plasma samples were from a local blood bank and stored at À80 C until use. Inactive hCES was prepared by denaturation using heat and organic solvent 4-fluoro-3a-tropacocaine and its 3b isomer were synthesized as described elsewhere (Kavanagh et al, 2012 (Darmstadt, Germany), ramipril from Hoechst (Frankfurt am Main, Germany), methylphenidate hydrochloride from Medice (Iserlohn, Germany), and thebacon and heroin hydrochloride were kindly provided by Prof. Robert Ammon (Homburg, Germany). Mitragynine was delivered from the Department of Forensic Medicine, Johannes Gutenberg University (Mainz, Germany), where it was isolated from kratom leaves obtained from Head & Nature (Regensburg, Germany) (Philipp et al, 2009).…”

Synthesis and In Vitro Evaluation of Tropane Halogenated-derivatives Against Malaria, Sleeping Sickness, Chagas Disease and Leishmaniasis

“…The in vitro antiprotozoal activity of compounds 1-13 was evaluated at the Laboratory of Microbiology, Parasitology and Hygiene (LMPH, University of Antwerp, Belgium) against red cell stages of P. falciparum K1, trypomastigotes of T. b. brucei, intracellular amastigotes of T. cruzi and L. infantum (Table 1). Compounds 3 [8], 5 and 13 [9] and 6 and 9 [10] have already been described in the literature but their antiparasitic activity has never been investigated before.…”

A high-affinity cocaine binding site associated with the brain acid soluble protein 1

“…Three of these drugs (benztropine, JHW007, and RTI-113) inhibit dopamine uptake ( 24 – 26 ). The pharmacology of the designer drug analog of cocaine 3-p-FBT has not been characterized ( 27 ). By contrast, tropane alkaloids, including benzocaine, atropine, and scopolamine, which lack dopamine uptake inhibitor activity, did not bind BASP1.…”