6-APDB

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran or as 4-desoxy-MDA, is an entactogen of the phenethylamine, amphetamine, and dihydrobenzofuran families.^[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] 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 and first described in 1993.^{[2][3][4][1][5][6]}

6-APDB

Clinical data
Other names	6-(2-Aminopropyl)-2,3-dihydrobenzofuran; 4-Desoxy-MDA; EMA-3; BF6AP
Routes of administration	Oral
Drug class	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 N
PubChem CID	192599
ChemSpider	167141 Y
UNII	O72F3CP4O8
ChEMBL	ChEMBL124055 Y
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 Y Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Interactions

See also: MDMA § Interactions, Trip killer § Antidotes of other hallucinogens, and MDMA/citalopram

Pharmacology

Pharmacodynamics

In animal drug discrimination 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] 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. It also has activities at serotonin receptors.^[7]

In subsequent animal studies, 6-APDB produced robust hyperlocomotion and, in drug discrimination tests, fully substituted for MDMA, partially substituted for DOM and cocaine, and failed to substitute for methamphetamine.^[8]

Chemistry

6-APDB, also known as 6-(2-aminopropyl)-2,3-dihydrobenzofuran, is a phenethylamine, amphetamine, and dihydrobenzofuran and an analogue of 3,4-methylenedioxyamphetamine (MDA).

Synthesis

The chemical synthesis of 6-APDB has been described.^[6]

Analogues

In contrast to 6-APDB, 5-APDB is highly selective for serotonin.^[1]

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.

History

6-APDB, along with 5-APDB, was described by David E. Nichols and colleagues at Purdue University as an MDMA analogue in 1993.^{[2][3][4][1][5][6]} Subsequently, the non-dihydrogenated benzofurans 5-APB and 6-APB emerged as novel designer drugs in 2010.^[4][3][1] Prior to this, 5-APB and 6-APB had been patented and first described by Eli Lilly and Company as serotonin 5-HT_2C receptor agonists for potential medical applications in 2000.^[2][3][4] 5-APB and 6-APB are often confused with 5-APDB and 6-APDB.^[3]

Society and culture

Legal status

United Kingdom

6-APDB is a class B drug in the United Kingdom since June 10, 2013. It is banned by a blanket law on benzofurans and related compounds.^[9]

See also

• Substituted benzofuran