General chemical structure of substituted benzofurans
Thesubstituted benzofurans are a class ofchemical compounds based on theheterocyclic andpolycyclic compoundbenzofuran. Many medicines use the benzofuran core as a scaffold,[1][2][3] but most commonly the term is used to refer to the simpler compounds in this class which include numerouspsychoactive drugs, includingstimulants,psychedelics andempathogens. In general, these compounds have a benzofuran core to which a 2-aminoethyl group is attached (at any position), and combined with a range of other substituents.[4][5][6][7] Some psychoactive derivatives from this family have been sold under the nameBenzofury.[8]
Substituted benzofurans saw widespread use asrecreational drugs by being sold asresearch chemicals making them exempt from drug legislation. Many of the more common compounds were banned in the UK in June 2013 astemporary class drugs, while others have been made permanently illegal in various jurisdictions.[34][35][36]
^Nevagi RJ, Dighe SN, Dighe SN (June 2015). "Biological and medicinal significance of benzofuran".European Journal of Medicinal Chemistry.97:561–81.doi:10.1016/j.ejmech.2014.10.085.PMID26015069.
^Nugteren-van Lonkhuyzen JJ, van Riel AJ, Brunt TM, Hondebrink L (December 2015). "Pharmacokinetics, pharmacodynamics and toxicology of new psychoactive substances (NPS): 2C-B, 4-fluoroamphetamine and benzofurans".Drug and Alcohol Dependence.157:18–27.doi:10.1016/j.drugalcdep.2015.10.011.PMID26530501.
^Liu C, Jia W, Qian Z, Li T, Hua Z (February 2017). "Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe".Drug Testing and Analysis.9 (2):199–207.doi:10.1002/dta.1955.PMID26856255.
^Barcelo B, Gomila I (2017). "Pharmacology and Literature Review Based on Related Death and Non-Fatal Case Reports of the Benzofurans and Benzodifurans Designer Drugs".Current Pharmaceutical Design.23 (36):5523–5529.doi:10.2174/1381612823666170714155140.PMID28714411.
^abcdefRoque 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.
^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]. [...] Information regarding the desired clinical effects of 5-APB and 6-APB is limited to on-line user report forums. Limited user reports indicate that positive effects of 5-APB include increased empathy, variable euphoria, visual disturbances, appreciation for music and dancing and more general 'stimulation' as opposed to 6-APB [12,23–25]. Reported positive effects of 6-APB include increased tactile and visual stimulation, mild euphoria, and appreciation for music, visual hallucinations and increase in mood, feelings of peace, love and self-acceptance [10,11,13,14].
^abcdefghiBrandt SD, Walters HM, Partilla JS, Blough BE, Kavanagh PV, Baumann MH (December 2020)."The psychoactive aminoalkylbenzofuran derivatives, 5-APB and 6-APB, mimic the effects of 3,4-methylenedioxyamphetamine (MDA) on monoamine transmission in male rats".Psychopharmacology (Berl).237 (12):3703–3714.doi:10.1007/s00213-020-05648-z.PMC7686291.PMID32875347.The synthetic preparation of both 5-APB and 6-APB was first published in 2000 as part of a research program designed for the development of selective 5-HT2C receptor agonists (Briner et al. 2000; Briner et al. 2006) [...] Briner K, Burkhart JP, Burkholder TP, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu Y-C, Xu Y (2000) Aminoalkylbenzofurans as serotonin (5-HT(2C)) agonists Patent No. WO2000044737A1, Eli Lilly and Company, Indianapolis, IN, USA, 2000. Briner K, Burkhart JP, Burkholder TP, Fisher MJ, Gritton WH, Kohlman DT, Liang SX, Miller SC, Mullaney JT, Xu YC (2006) Aminoalkylbenzofurans as serotonin (5-HT(2C)) agonists Patent No. US7045545B1, Eli Lilly and Company, Indianapolis, IN, USA, 2006.
^Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain".European Journal of Pharmacology.559 (2–3):132–137.doi:10.1016/j.ejphar.2006.11.075.PMID17223101.
^Monte 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.
^Dawson P, Opacka-Juffry J, Moffatt JD, Daniju Y, Dutta N, Ramsey J, Davidson C (January 2014). "The effects of benzofury (5-APB) on the dopamine transporter and 5-HT2-dependent vasoconstriction in the rat".Prog Neuropsychopharmacol Biol Psychiatry.48:57–63.doi:10.1016/j.pnpbp.2013.08.013.PMID24012617.
^"关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe original on 1 October 2015. Retrieved23 August 2016.
^Tomaszewski Z, Johnson MP, Huang X, Nichols DE (May 1992). "Benzofuran bioisosteres of hallucinogenic tryptamines".Journal of Medicinal Chemistry.35 (11):2061–4.doi:10.1021/jm00089a017.PMID1534585.
^Monte 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".Journal of Medicinal Chemistry.36 (23):3700–6.doi:10.1021/jm00075a027.PMID8246240.
^US patent 7045545, Karin Briner, Joseph Paul Burkhart, Timothy Paul Burkholder, Matthew Joseph Fisher, William Harlan Gritton, Daniel Timothy Kohlman, Sidney Xi Liang, Shawn Christopher Miller, Jeffrey Thomas Mullaney, Yao-Chang Xu, Yanping Xu, "Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists", published 19 January 2000, issued 16 May 2006
^Stanczuk A, Morris N, Gardner EA, Kavanagh P (April 2013). "Identification of (2-aminopropyl)benzofuran (APB) phenyl ring positional isomers in internet purchased products".Drug Testing and Analysis.5 (4):270–6.doi:10.1002/dta.1451.PMID23349125.
^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):302–4.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):276–81.doi:10.1021/jm00105a043.PMID1992127.
^Monte AP, Marona-Lewicka D, Parker MA, Wainscott DB, Nelson DL, Nichols DE (July 1996). "Dihydrobenzofuran analogues of hallucinogens. 3. Models of 4-substituted (2,5-dimethoxyphenyl)alkylamine derivatives with rigidified methoxy groups".Journal of Medicinal Chemistry.39 (15):2953–61.doi:10.1021/jm960199j.PMID8709129.
^Liu C, Jia W, Qian Z, Li T, Hua Z (February 2017). "Identification of five substituted phenethylamine derivatives 5-MAPDB, 5-AEDB, MDMA methylene homolog, 6-Br-MDMA, and 5-APB-NBOMe".Drug Testing and Analysis.9 (2):199–207.doi:10.1002/dta.1955.PMID26856255.
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