6-APDB
File:4-desoxy-MDA.svg | |
Systematic (IUPAC) name | |
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1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine | |
Clinical data | |
Pregnancy category |
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Routes of administration | Oral |
Legal status | |
Legal status |
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Identifiers | |
CAS Number | 152623-93-3 |
ATC code | none |
PubChem | CID 192599 |
ChemSpider | 167141 |
Chemical data | |
Formula | C11H15NO |
Molar mass | 177.24 g/mol[[Script error: No such module "String".]] |
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 group.[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,[1] but the difference in pharmacological effects between 6-APB and 6-APDB is unclear.
See also
- 6-APB
- 5-APDB
- 5-(2-Aminopropyl)indole
- Ethylenedioxymethamphetamine
- Indanylaminopropane
- Naphthylaminopropane
- Tetralinylaminopropane
References
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Aminoindanes | |
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Aminotetralins | |
Phenethylamines (and amphetamines, cathinones, etc) | 2-Methyl-MDA • 4-CAB • 4-FA • 4-FMA • 4-MTA • 5-APDB • 5-Methyl-MDA • 6-APDB • 6-Methyl-MDA • Ariadne • BDB • BOH • Brephedrone • Butylone • DMMDA • DMMDA-2 • EBDB • EBDP • EDMA • Ethylone • Eutylone • Fenfluramine (also dexfenfluramine) • Flephedrone • IAP • IMP • Lophophine • MBDB • MBDP • MDA • MDDM • MDEA • MDIP • MDMA • MDMOH • MDMP • MDMPEA • MDOH • MDPEA • MDPH • MDPR • Mephedrone • Methedrone • Methylone • MMA • MMDA • MMDMA • NAP • Norfenfluramine • Pentylone • PMA • PMEA • PMMA • TAP |
Tryptamines |
Phenethylamines | Psychedelics: 2C-B • 2C-B-FLY • 2C-C • 2C-D • 2C-E • 2C-G • 2C-I • 2C-N • 2C-P • 2C-SE • 2C-T • 2C-T-2 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 2C-T-9 • 2C-T-13 • 2C-T-15 • 2C-T-17 • 2C-T-21 • 2C-TFM • 2C-YN • Allylescaline • DESOXY • Escaline • Isoproscaline • Jimscaline • Macromerine • MEPEA • Mescaline • Metaescaline • Methallylescaline • Proscaline • Psi-2C-T-4 • TCB-2 Stimulants: 2-OH-PEA • β-Me-PEA • Hordenine • N-Me-PEA • Phenethylamine (PEA) Entactogens: Lophophine • MDPEA • MDMPEA Others: BOH • DMPEA |
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Amphetamines Phenylisopropylamines | Psychedelics: 3C-BZ • 3C-E • 3C-P • Aleph • Beatrice • Bromo-DragonFLY • D-Deprenyl • DMA • DMCPA • DMMDA • DOB • DOC • DOEF • DOET • DOI • DOM • DON • DOPR • DOTFM • Ganesha • MMDA • MMDA-2 • Psi-DOM • TMA • TeMA Stimulants: 4-MA • 4-MMA • 4-MTA • 5-IT • Alfetamine • Amfecloral • Amfepentorex • Amphetamine (Dextroamphetamine, Levoamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • Cathine • Clobenzorex • Dimethylamphetamine • Ephedrine (EPH) • Ethylamphetamine • Fencamfamine • Fencamine • Fenethylline • Fenfluramine (Dexfenfluramine) • Fenproporex • Fludorex • Furfenorex • Isopropylamphetamine • Lefetamine • Mefenorex • Methamphetamine (Dextromethamphetamine, Levomethamphetamine) • Methoxyphenamine • MMA • Oxilofrine • Ortetamine • PBA • PCA • Phenpromethamine • PFA • PFMA • PIA • PMA • PMEA • PMMA • Phenylpropanolamine (PPA) • Prenylamine • Propylamphetamine • Pseudoephedrine (PSE) • Sibutramine • Tiflorex (Flutiorex) • Tranylcypromine • Xylopropamine • Zylofuramine Entactogens: 5-APDB • 6-APB • 6-APDB • IAP • MDA • MDEA • MDHMA (FLEA) • MDMA ("Ecstasy") • MDOH • MMDMA • NAP • TAP Others: Amiflamine • D-Deprenyl • L-Deprenyl (Selegiline) |
Phentermines | Stimulants: Chlorphentermine • Cloforex • Clortermine • Etolorex • Mephentermine • Pentorex (Phenpentermine) • Phentermine Entactogens: MDPH • MDMPH |
Cathinones | Stimulants: Amfepramone • Brephedrone • Buphedrone • Bupropion (Amfebutamone) • Cathinone (Propion) • Dimethylcathinone (Dimethylpropion, Metamfepramone) • Ethcathinone (Ethylpropion) • Flephedrone • Methcathinone (Methylpropion) • Mephedrone • Methedrone Entactogens: Ethylone • Methylone |
Phenylisobutylamines | |
Phenylalkylpyrrolidines | |
Catecholamines (and relatives..) | 6-FNE • 6-OHDA • α-Me-DA • α-Me-TRA • Adrenochrome • Ciladopa • D-DOPA (Dextrodopa) • Dopamine • Epinephrine (Adrenaline) • Epinine • Fenclonine • Ibopamine • L-DOPA (Levodopa) • L-DOPS (Droxidopa) • L-Phenylalanine • L-Tyrosine • meta-Octopamine • meta-Tyramine • Metanephrine • Metirosine • Methyldopa • Nordefrin (Levonordefrin) • Norepinephrine (Noradrenaline) • Normetanephrine • para-Octopamine • para-Tyramine |
Miscellaneous | Amidephrine • Arbutamine • Cafedrine • Denopamine • Dobutamine • Dopexamine • Etafedrine • Ethylnorepinephrine • Etilefrine • Famprofazone • Gepefrine • Isoprenaline (Isoproterenol) • Isoetarine • Metaraminol • Metaterol • Methoxamine • Norfenefrine • Orciprenaline • Phenylephrine (Neosynephrine) • Phenoxybenzamine • Prenalterol • Pronethalol • Propranolol • Salbutamol (Albuterol; Levosalbutamol) • Synephrine (Oxedrine) • Theodrenaline • Xamoterol |
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- Amphetamines
- Benzofurans
- Entactogens and Empathogens
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