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6-(2-Aminopropyl)-2,3-dihydrobenzofuran

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6-(2-Aminopropyl)-2,3-dihydrobenzofuran

6-(2-Aminopropyl)-2,3-dihydrobenzofuran (6-APDB, 4-Desoxy-MDA, EMA-3) is a stimulant and entactogen drug of the phenethylamine and amphetamine classes.[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] 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues.[1]

In animal 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] 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 its in vitro profile it can be suggested that it may have amphetamine-like effects at higher doses.

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

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