6-APDB

6-APDB

6-APDB
Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
Clinical data
Pregnancy cat.
  • ?
Legal status
Routes Oral
Identifiers
CAS number  N
ATC code None
PubChem
ChemSpider  YesY
ChEMBL  YesY
Chemical data
Formula C11H15NO 
Mol. mass 177.24 g/mol
 N   

6-(2-Aminopropyl)-2,3-dihydrobenzofuran (6-APDB, 4-Desoxy-MDA, EMA-3) is a 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, 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]


See also

References

  1. ^ a b c d e f g h 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.  
  2. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.