5-APDB

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5-APDB
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Clinical data
Other names5-(2-Aminopropyl)-2,3-dihydrobenzofuran; 3-Desoxy-MDA; EMA-4; BF5AP
Routes of
administration		Oral
Drug classEntactogen; Serotonin releasing agent; Serotonin receptor modulator
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  • None
Legal status
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Identifiers
  • 1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-amine
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Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
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  • CC(CC1=CC2=C(C=C1)OCC2)N
  • InChI=1S/C11H15NO/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11/h2-3,7-8H,4-6,12H2,1H3 checkY
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5-APDB, also known as 5-(2-aminopropyl)-2,3-dihydrobenzofuran or as 3-desoxy-MDA, is an entactogen of the phenethylamine, amphetamine, and dihydrobenzofuran families.[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA and first described in 1993.[3][4][5][6][7][2]

Interactions

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Pharmacology

Pharmacodynamics

In animal drug discrimination studies, 5-APDB's effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, while producing no substitution for LSD or amphetamine.[2] In vitro studies show that 5-APDB acts as a highly selective serotonin releasing agent (SSRA), with IC50 values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.[2] It also has activities at serotonin receptors.[6]

Chemistry

5-APDB, also known as 5-(2-aminopropyl)benzofuran, is a phenethylamine, amphetamine, and benzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Synthesis

The chemical synthesis of 5-APDB has been described.[2]

Analogues

In contrast to 5-APDB, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[2]

Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around one tenth as potent as DOM.[8][9]

History

5-APDB, along with 6-APDB, was described by David E. Nichols and colleagues at Purdue University as an MDMA analogue in 1993.[3][4][5][6][7][2] Subsequently, the non-dihydrogenated benzofurans 5-APB and 6-APB emerged as novel designer drugs in 2010.[5][4][6] Prior to this, 5-APB and 6-APB had been patented and first described by Eli Lilly and Company as serotonin 5-HT2C receptor agonists for potential medical applications in 2000.[3][4][5] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.[4]

Society and culture

Canada

5-APDB is a Schedule I controlled substance in Canada due phenethylamine blanket-ban language.[10]

China

As of October 2015 5-APDB is a controlled substance in China.[11]

United Kingdom

On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[12] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[13]

United States

5-APDB is not an explicitly controlled substance in the United States.[14] However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content.Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in português do Brasil). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ^ a b c d e f g h i Page Module:Citation/CS1/styles.css has no content.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. PMID 8246240.
  3. ^ a b c Page Module:Citation/CS1/styles.css has no content.Brandt 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. PMC 7686291. PMID 32875347. 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), and the preparation of other isomers was reported for forensic purposes a decade later (Casale and Hays 2012; Stanczuk et al. 2013).
  4. ^ a b c d e Page Module:Citation/CS1/styles.css has no content.Roque 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. PMID 30723925. 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).
  5. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Greene, Shaun L (2013). "Benzofurans and Benzodifurans". Novel Psychoactive Substances. Elsevier. p. 383–392. doi:10.1016/b978-0-12-415816-0.00016-x. ISBN 978-0-12-415816-0. Retrieved 2 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]. [...]
  6. ^ a b c d Page Module:Citation/CS1/styles.css has no content.Rickli 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. PMC 4500375. PMID 25765500. [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).
  7. ^ a b Page Module:Citation/CS1/styles.css has no content.Nichols DE (1994). "Medicinal Chemistry and Structure–Activity Relationships". In Cho AK, Segal DS (eds.). Amphetamine and Its Analogs: Psychopharmacology, Toxicology, and Abuse. Academic Press. pp. 3–41. ISBN 978-0-12-173375-9. Very recently, the oxygen atoms in the dioxole ring of MDA were replaced individually with methylene units to give compounds 25, 26, and 27. In addition, the ring-expanded compound 28 was prepared for comparison. [...]
  8. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 3950910.
  9. ^ Page Module:Citation/CS1/styles.css has no content.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. PMID 1992127.
  10. ^ Page Module:Citation/CS1/styles.css has no content."Controlled Drugs and Substances Act". Department of Justice Canada. 5 December 2025. Retrieved 20 January 2026.
  11. ^ Page Module:Citation/CS1/styles.css has no content."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 中文). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  12. ^ Page Module:Citation/CS1/styles.css has no content."Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Archived from the original on 2017-08-24. Retrieved 2013-06-13.
  13. ^ Page Module:Citation/CS1/styles.css has no content."'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Archived from the original on 2013-09-21. Retrieved 2013-06-13.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026

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