6-APDB

6-APDB
Clinical data
Routes of; administration	By mouth
Drug class	Empathogen–entactogen; Stimulant
ATC code	None;
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine;
CAS Number	152623-93-3 ;
PubChem CID	192599;
ChemSpider	167141 ;
UNII	O72F3CP4O8;
ChEMBL	ChEMBL124055 ;
CompTox Dashboard (EPA)	DTXSID60934559 ;
Chemical and physical data
Formula	C11H15NO
Molar mass	177.247 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N ;
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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]

^ ^a ^b ^c ^d 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. doi:10.1021/jm00075a027. PMID 8246240.

[pmid8246240-1] 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. doi:10.1021/jm00075a027. PMID 8246240.

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