5-APDB

5-APDB
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	CA: Schedule I UK: Class B
Identifiers
IUPAC name 1-(2,3-Dihydro-1-benzofuran-5-yl)propan-2-amine
CAS Number	152624-03-8^N
PubChem CID	192601
ChemSpider	167143^N
UNII	UI10BAJ8SH
Chemical and physical data
Formula	C₁₁H₁₅NO
Molar mass	177.242 g/mol
3D model (Jmol)	Interactive image
SMILES Cl.CC(N)Cc1cc2CCOc2cc1
InChI InChI=1S/C11H15NO.ClH/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11;/h2-3,7-8H,4-6,12H2,1H3;1H^Y Key:BZKLFXQUBIRXAK-UHFFFAOYSA-N^Y
^NY (what is this?)

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes. It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge. 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead. 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues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.

In animal studies, 5-APDB's effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, while producing no substitution for LSD or amphetamine.In vitro studies show that 5-APDB acts as a highly selective serotonin releasing agent (SSRA), with IC₅₀ values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively. In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.