6-APDB

Last updated
6-APDB
4-desoxy-MDA.svg
6-APDB molecule ball.png
Clinical data
Other names6-(2-Aminopropyl)-2,3-dihydrobenzofuran; 4-Desoxy-MDA; EMA-3; BF6AP
Routes of
administration 		Oral
Drug class Entactogen; Stimulant
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO
Molar mass 177.247 g·mol−1
3D model (JSmol)
  • O2c1cc(ccc1CC2)CC(N)C
  • InChI=1S/C11H15NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-3,7-8H,4-6,12H2,1H3 Yes check.svgY
  • Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran or as 4-desoxy-MDA, is an entactogen of the phenethylamine, amphetamine, and dihydrobenzofuran families. [1] It is an analogue of MDA where the heterocyclic 4-position oxygen from the 3,4-methylenedioxy ring has been replaced with a methylene bridge. [1] 5-APDB (3-desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. [1] 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. [2] [3] [4] [1] [5] [6]

Contents

Interactions

Pharmacology

Pharmacodynamics

In animal drug discrimination studies, 6-APDB fully substitutes for MBDB and MMAI but not for amphetamine or LSD. [1] In vitro , 6-APDB has been shown to inhibit the reuptake of serotonin, dopamine, and norepinephrine with IC50 values of 322 nM, 1,997 nM, and 980 nM, respectively. [1] These values are very similar to those of MDA, but with those for the catecholamines slightly lower in comparison, perhaps more similarly to MDMA. [1] Though 6-APDB does not substitute for amphetamine in rats at the doses used in referenced study, based on its in vitro profile it can be suggested that it may have amphetamine-like effects at higher doses. It also has activities at serotonin receptors. [7]

In subsequent animal studies, 6-APDB produced robust hyperlocomotion and, in drug discrimination tests, fully substituted for MDMA, partially substituted for DOM and cocaine, and failed to substitute for methamphetamine. [8]

Chemistry

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a phenethylamine, amphetamine, and dihydrobenzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Synthesis

The chemical synthesis of 6-APDB has been described. [6]

Analogues

In contrast to 6-APDB, 5-APDB is highly selective for serotonin. [1]

The unsaturated benzofuran derivative 6-APB, or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.

History

6-APDB, along with 5-APDB, was described by David E. Nichols and colleagues at Purdue University as an MDMA analogue in 1993. [2] [3] [4] [1] [5] [6] Subsequently, the non-dihydrogenated benzofurans 5-APB and 6-APB emerged as novel designer drugs in 2010. [4] [3] [1] 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. [2] [3] [4] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB. [3]

Society and culture

United Kingdom

6-APDB is a class B drug in the United Kingdom since June 10, 2013. It is banned by a blanket law on benzofurans and related compounds. [9]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 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. PMID   8246240.
  2. 1 2 3 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).
  3. 1 2 3 4 5 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).
  4. 1 2 3 4 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]. [...]
  5. 1 2 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. [...]
  6. 1 2 3 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.
  7. ↑ Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015). "Pharmacological profile of novel psychoactive benzofurans". Br J Pharmacol. 172 (13): 3412–3425. doi:10.1111/bph.13128. PMC   4500375 . PMID   25765500.
  8. ↑ Dolan SB, Forster MJ, Gatch MB (November 2017). "Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine". Drug Alcohol Depend. 180: 39–45. doi:10.1016/j.drugalcdep.2017.07.041. PMC   6463889 . PMID   28865391.
  9. ↑ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Archived from the original on 2014-12-04. Retrieved 2014-03-11.
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