The Toll of Benzofurans in the Context of Drug Abuse

Bravo, Rita Roque; Silva, João Pedro; Carmo, Helena; Carvalho, Félix; Silva, Diana Dias da

doi:10.1007/978-3-030-92392-1_168

Cited by 1 publication

(1 citation statement)

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“…5-(2-Aminopropyl) benzofuran (5-APB) and 6-(2-aminopropyl) benzofuran (6-APB) were initially synthesized for research purposes [2] and made their appearance on the drug scene in 2010. These benzofurans have a similar chemical structure to MDMA (ecstasy) and MDA (Figure 1), two well-known illicit drugs [3,4]. Due to their popularity among users, reports of serious intoxication, including some fatalities, have emerged (there have been several fatal cases of the simultaneous consumption of 5-APB and 6-APB) [5][6][7][8][9][10].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-(5-(2-Aminopropyl)-2-hydroxyphenyl)acetic Acid, a Metabolite of the Drug 5-APB

Silva

Fino

Ferreira

et al. 2023

Molbank

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5-(2-Aminopropyl)benzofuran (5-APB), also known as “Benzo Fury,” is a novel psychoactive substance (NPS) belonging to a new class of synthetic phenethylamines. It acts by disrupting serotonergic circuits as a serotonin–norepinephrine–dopamine reuptake inhibitor and is classified as an entactogen, similar to MDMA and MDA. Despite its popularity among users, recent toxicity events have been associated with the consumption of 5-APB and other benzofurans, highlighting the need for a better understanding of their pharmacodynamics and toxicity. One way to achieve this is by developing the synthesis of 5-APB metabolites as biomarkers of exposure. In this study, we present a six-step synthesis for one of the 5-APB metabolites, 2-(5-(2-aminopropyl)-2-hydroxyphenyl)acetic acid (1), involving methylation, formylation, Aldol-type condensation, reduction, and hydrolysis reactions. The compound was obtained in an overall yield of 11%.

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