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| Routes of administration | By mouth |
| Drug class | Empathogen–entactogen;Stimulant |
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| Formula | C11H15NO |
| Molar mass | 177.247 g·mol−1 |
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6-(2-Aminopropyl)-2,3-dihydrobenzofuran (6-APDB,4-Desoxy-MDA,EMA-3) is astimulant andentactogendrug of thephenethylamine andamphetamine classes.[1] It is ananalogue ofMDA where theheterocyclic 4-positionoxygen from the 3,4-methylenedioxyring has been replaced with amethylene 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] 6-APDB, along with 5-APDB, was firstsynthesized byDavid E. Nichols in the early 1990s while investigating non-neurotoxicMDMAanalogues.[1]
In animal studies, 6-APDB fully substitutes forMBDB andMMAI but not foramphetamine orLSD.[1]In vitro, 6-APDB has been shown toinhibit thereuptake ofserotonin,dopamine, andnorepinephrine withIC50 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 thecatecholamines slightly lower in comparison, perhaps more similarly to MDMA.[1] In contrast, 5-APDB is highly selective for serotonin.[1] Though 6-APDB does not substitute for amphetamine in rats at the doses used in referenced study, based on itsin vitro profile it can be suggested that it may have amphetamine-like effects at higher doses.
The unsaturated benzofuran derivative6-APB, or 6-(2-aminopropyl)benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.
6-APDB is a class B drug in the UK since June 10, 2013. It is banned by a blanket law on benzofurans and related compounds.[2]
