6-APDB

6-APDB

Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes	Oral
Identifiers
CAS number	152623-93-3 N
ATC code	None
PubChem	CID 192599
ChemSpider	167141 Y
ChEMBL	CHEMBL124055 Y
Chemical data
Formula	C11H15NO
Mol. mass	177.24 g/mol
SMILES O2c1cc(ccc1CC2)CC(N)C
InChI InChI=1S/C11H15NO/c1-8(12)6-9-2-3-10-4-5-13-11(10)7-9/h2-3,7-8H,4-6,12H2,1H3 Y Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N Y
N (what is this?)  (verify)

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.

See also

• 5-APB
• 6-APB
• 5-APDB
• 5-(2-Aminopropyl)indole
• Ethylenedioxymethamphetamine
• Indanylaminopropane
• Naphthylaminopropane
• Tetralinylaminopropane

References