Benzo fury: A new trend in the drug misuse scene

Abstract

Benzofurans, also known by users as benzo fury or benzofury, are synthetic phenethylamines and constitute the third most prominent group of new psychoactive substances (NPS). As the use of these substances has been spread as an alternative to the classic illicit psychostimulants, such as amphetamines, their legal status was reviewed, resulting in an utter prohibition of these NPS in many countries worldwide.Herein, the prevalence of abuse, chemistry, biological effects, metabolism, and the potential harms and risky behaviors associated with the abuse of benzofurans are reviewed. The congeners of this group are mainly consumed recreationally at electronic dance music parties, in polydrug abuse settings. Benzofurans preferentially act by disturbing the functioning of serotonergic circuits, which induces their entactogenic and stimulant effects and is the reason behind the considerable number of recent benzo fury-related deaths. The slight interaction of these drugs with the dopaminergic system justifies the rewarding effects of these drugs. To date, published evidence on the mechanisms of toxicity of benzo fury is very limited but a body of research is now beginning to emerge revealing an alarming public health threat regarding the abuse of these NPS.

Beyond ecstasy: Alternative entactogens to 3,4-methylenedioxymethamphetamine with potential applications in psychotherapy

“… 1) MAPS (2019); 2) Baggott et al (2019); 3) Shulgin and Shulgin (1991); 4) Ensslin et al (1996); 5) Brunnenberg et al (1998); 6) Kelly (2011); 7) Erowid ‘Ethylone’ (2006a); 8) Erowid ‘Butylone’ (2005a); 9) Roque Bravo et al (2019); 10) Drugs Forum ‘6-MAPB’ (2011); 11) Erowid ‘5-MAPB’ (2014); 12) Erowid ‘MDAI’ (2010); 13) Drugs Forum ‘5-IAI’ (2010); 14) Shulgin and Shulgin (1997); 15) Dolder et al (2018a); 16) de Sousa Fernandes Perna et al (2018). * Dose estimated from anecdotal user reports. 5-APB: 5-(2-aminopropyl)-benzofuran; 6-APB: 6-(2-aminopropyl)-benzofuran; α-ET: α-ethyltryptamine; 4-FA: 4-fluoroamphetamine; 5-IAI: 5-iodo-2-aminoindane; 6-MAPB: 5-(2-methylaminopropyl)benzofuran; MDA: 3,4-methylenedioxyamphetamine; MDMA: 3,4-methylenedioxy-N-methylamphetamine; MBDB: 1-(1,3-benzodioxol-5-yl)- N -methyl-2-butanamine; MDAI: 5,6-methylenedioxy-2-aminoindane; MDEA: 3,4-methylenedioxy-N-ethyl-amphetamine. …”

“… 1) MAPS (2019) ; 2) Baggott et al (2019) ; 3) Shulgin and Shulgin (1991) ; 4) Ensslin et al (1996) ; 5) Brunnenberg et al (1998) ; 6) Kelly (2011) ; 7) Erowid ‘Ethylone’ (2006a) ; 8) Erowid ‘Butylone’ (2005a) ; 9) Roque Bravo et al (2019) ; 10) Drugs Forum ‘6-MAPB’ (2011) ; 11) Erowid ‘5-MAPB’ (2014) ; 12) Erowid ‘MDAI’ (2010) ; 13) Drugs Forum ‘5-IAI’ (2010) ; 14) Shulgin and Shulgin (1997) ; 15) Dolder et al (2018a) ; 16) de Sousa Fernandes Perna et al (2018) . * Dose estimated from anecdotal user reports.…”

“…To date, no research has been conducted to ascertain the neurotoxic potential of benzofurans ( Roque Bravo et al., 2019 ). There are, however, some indications coming from user reports: 5-APB and 6-APB are generally claimed to produce less of a ‘come down’, a period following the acute effects of a drug, characterised by depressed thoughts, lack of energy and general malaise, than MDMA ( Supplementary file : Erowid ‘5-APB’, 2011 , (1); Erowid ‘5-MAPB’, 2014 , (3)); Reddit ‘6-APB’, 2018 ).…”

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

“…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].…”

Recent Advances Towards the Synthesis of Dihydrobenzofurans and Dihydroisobenzofurans

“…The Kadsurenone ( 18 ) neolignan has platelet‐activating factor (PAF) antagonist property, [50,51] and it extracts from stems of piper kadsura [52,53] . The structures 6‐MAPDB ( 19 ), 5‐MAPDB ( 20 ), 6‐APDB ( 21 ), and 5‐APDB ( 22 ) all are entactogenic drugs, and the 5‐APDB ( 22 ) is a highly selective serotonin‐releasing agent (SSRA) [54,55] . Furthermore, the dihydrobenzofuran derivatives ( 23 ‐ 28 ) have been discovered in various species of higher plants and the Asteraceae family, all with critical biological activities (Figure 3).…”