5-APDB

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classes.^[2] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.^[2] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.^[2] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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

5-APDB

Clinical data
Routes of administration	Oral
ATC code	None
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] CA: Schedule I DE: NpSG (Industrial and scientific use only) 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
CompTox Dashboard (EPA)	DTXSID70934560
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	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?)  (verify)

Pharmacology

In animal drug discrimination 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.^[2] 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.^[2] It also has activities at serotonin receptors.^[3]

Chemistry

Analogues

In contrast to 5-APDB, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.^[2]

Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around one tenth as potent as DOM.^[4][5]

Society and culture

Legal status

China

As of October 2015 5-APDB is a controlled substance in China.^[6]

United Kingdom

On June 10, 2013, 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.^[7] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.^[8]