6-APDB
6-APDB, also known as 6--2,3-dihydrobenzofuran or as 4-desoxy-MDA, is an entactogen of the phenethylamine, amphetamine, and dihydrobenzofuran families. 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. 5-APDB is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 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.
Pharmacology
Pharmacodynamics
In animal drug discrimination studies, 6-APDB fully substitutes for MBDB and MMAI but not for amphetamine or LSD. 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. These values are very similar to those of MDA, but with those for the catecholamines slightly lower in comparison, perhaps more similarly to MDMA. 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.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.
Chemistry
6-APDB, also known as 6--2,3-dihydrobenzofuran, is a phenethylamine, amphetamine, and dihydrobenzofuran and an analogue of 3,4-methylenedioxyamphetamine.Synthesis
The chemical synthesis of 6-APDB has been described.Analogues
In contrast to 6-APDB, 5-APDB is highly selective for serotonin.The unsaturated benzofuran derivative 6-APB, or 6-benzofuran is also known, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.