Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted forDOM in animal tests, although they were around one tenth as potent as DOM.[8][9]
On June 10, 2013, 5-APDB and a number of analogues were classified asTemporary Class Drugs in the UK following an ACMD recommendation.[11] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[12]
^abcdefghiMonte AP, Marona-Lewicka D, Cozzi NV, Nichols DE (November 1993). "Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine".J Med Chem.36 (23):3700–3706.doi:10.1021/jm00075a027.PMID8246240.
^abcdeRoque Bravo R, Carmo H, Carvalho F, Bastos ML, Dias da Silva D (August 2019). "Benzo fury: A new trend in the drug misuse scene".J Appl Toxicol.39 (8):1083–1095.doi:10.1002/jat.3774.PMID30723925.The first benzofurans appearing on the drug scene in 2010‐11, were 5‐(2‐aminopropyl) benzofuran (5‐APB) and 6‐(2‐aminopropyl) benzofuran (6‐APB). These compounds had been previously patented in 2006 as potential therapeutic drugs for eating disorders and seizures, due to their action as serotonergic agonists (Advisory Council on the Misuse of Drugs, 2013; Taschwer, Hofer, & Schmid, 2014). While these first two molecules are the subject of most published investigations, namely those concerning pharmacological aspects, other benzofuran analogues have also been marketed as "legal highs." Examples of such analogues are 5‐(2‐ aminopropyl)‐2,3‐dihydrobenzofuran (5‐APDB) and 6‐(2‐aminopropyl)‐ 2,3‐dihydrobenzofuran (6‐APDB), first synthesized in 1993, purportedly as non‐neurotoxic benzofuran analogues of 3,4‐methylenedioxyamphetamine (MDA) (Monte, Marona‐Lewicka, Cozzi, & Nichols, 1993). These drugs are often confused with 5‐APB and 6‐APB (Casale, 2012; Casale & Hays, 2011).
^abcdGreene, Shaun L (2013). "Benzofurans and Benzodifurans".Novel Psychoactive Substances. Elsevier. p. 383–392.doi:10.1016/b978-0-12-415816-0.00016-x.ISBN978-0-12-415816-0. Retrieved2 November 2025.A patent granted to Eli Lilly and Company in 2006 classifies 5-APB and 6-APB as 5HT2C receptor agonists [15]. [...] Internet user reports of 5-APB and 6-APB date from late 2010 [13]. [...]
^abcdRickli A, Kopf S, Hoener MC, Liechti ME (July 2015)."Pharmacological profile of novel psychoactive benzofurans".British Journal of Pharmacology.172 (13):3412–3425.doi:10.1111/bph.13128.PMC4500375.PMID25765500.[5-APB] and [6-APB] are benzofuran analogues of MDA (Figure 1). [5-APDB] and [6-APDB] are dihydrobenzofuran analogues (Figure 1) that were originally synthesized for research purposes (Monte et al., 1993). [...] 5-APB and 6-APB appeared on the drug market in 2010– 2011 (Chan et al., 2013; Jebadurai et al., 2013; Stanczuk et al., 2013; Archer et al., 2014; Elliott and Evans, 2014; King, 2014), with reports of intoxication (Chan et al., 2013; Greene, 2013; Jebadurai et al., 2013; Seetohul and Pounder, 2013).
^Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats".Journal of Medicinal Chemistry.29 (2):302–304.doi:10.1021/jm00152a022.PMID3950910.
^Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines".Journal of Medicinal Chemistry.34 (1):276–281.doi:10.1021/jm00105a043.PMID1992127.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" [Notice on Printing and Distributing the "Measures for the Scheduling of Non-Pharmaceutical Narcotic Drugs and Psychotropic Substances"] (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved1 October 2015.
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