6-APDB
- ?
administration
- none
- CA: Schedule I
- DE: NpSG (Industrial and scientific use only)
- UK: Class B
- 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
- 152623-93-3 N
- 192599
- 167141 Y
- O72F3CP4O8
- ChEMBL124055 Y
- DTXSID60934559
- Interactive image
- O2c1cc(ccc1CC2)CC(N)C
- 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
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, but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.
6-APDB is a class B drug in the UK since June 10, 2013. It is banned by a blanket law on benzofurans and related compounds.[2]
References
- ^ a b c d e f g h 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.
- ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.
- v
- t
- e
amines
(other than
cathinones)
- Unfused benzene ring: 3-CMA
- 4-CAB
- 4-FA
- 4-MA
- 4-MMA
- 4-FMA
- 4-MTA
- 4,4'-DMAR
- Ariadne
- Metaescaline
- MMA
- PMA
- PMEA
- PMMA
- mMMA
Benzodioxine: EDMA
Benzodioxoles: Phenethylamine: { Lophophine } - Amphetamines: { 2-Methyl-MDA
- 2,3-MDA
- 3,4-MDA (tenamfetamine)
- 5-Methyl-MDA
- 6-Methyl-MDA
- DFMDA
- DMMDA
- DMMDA-2
- EIDA
- Lys-MDA
- MDEA
- MDMA (midomafetamine)
- MDMOH
- MDOH
- MMDA
- MMDA-2
- MMDMA
- N-t-BOC-MDMA }
- 1-Phenylbutan-2-amines: { BDB
- EBDB
- MBDB }
- Phentermines: { MDMP
- MDPH }
Benzofurans, dihydrobenzofurans and benzothiophenes: 2-MAPB - 5-APB
- 5-APDB
- 5-EAPB
- 5-MAPB
- 5-MAPDB
- 5-MAPBT
- 5-MBPB
- 6-APB
- 6-APDB
- 6-EAPB
- 6-MAPB
- 6-MAPDB
- IBF5MAP
Indanes: 5-APDI - 5-MAPDI
Indoles: 5-IT - 6-API
Naphthalenes: Methamnetamine - Naphthylaminopropane
Tetralin: 6-APT
alkylamines