6-APDB (original) (raw)
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. 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. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues.
| Property | Value |
|---|---|
| dbo:abstract | 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. 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. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues. In animal studies, 6-APDB fully substitutes for MBDB and MMAI but not for amphetamine or LSD. 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. These values are very similar to those of MDA, but with those for the catecholamines slightly lower in comparison, perhaps more similarly to MDMA. In contrast, 5-APDB is highly selective for serotonin. 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. (en) |
| dbo:casNumber | 152623-93-3 |
| dbo:chEMBL | 124055 |
| dbo:fdaUniiCode | O72F3CP4O8 |
| dbo:pubchem | 192599 |
| dbo:thumbnail | wiki-commons:Special:FilePath/4-desoxy-MDA.svg?width=300 |
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| dbo:wikiPageWikiLink | dbr:Methylene_bridge dbr:Methylenedioxy dbr:David_E._Nichols dbr:In_vitro dbr:Structural_analog dbr:Substituted_amphetamine dbr:Reuptake_inhibitor dbr:1,3-Benzodioxolyl-N-methylbutanamine dbc:Designer_drugs dbc:Entactogens_and_empathogens dbc:Serotonin-norepinephrine-dopamine_releasing_agents dbr:Functional_group dbr:Organic_synthesis dbr:Stimulant dbc:6-Benzofuranethanamines dbr:Drug dbr:5-APDB dbr:6-APB dbr:Amphetamine dbr:Norepinephrine dbr:Oxygen dbc:Substituted_amphetamines dbr:LSD dbr:Dopamine dbr:3,4-methylenedioxyamphetamine dbr:Entactogen dbr:Neurotoxic dbr:Catecholamine dbr:Serotonin dbr:Substituted_phenethylamine dbr:IC50 dbr:Reuptake dbr:Heterocyclic dbr:3,4-methylenedioxymethamphetamine dbr:5-methoxy-6-methyl-2-aminoindane |
| dbp:alt | Ball-and-stick model of the 6-APDB molecule (en) |
| dbp:atcPrefix | none (en) |
| dbp:c | 11 (xsd:integer) |
| dbp:casNumber | 152623 (xsd:integer) |
| dbp:chembl | 124055 (xsd:integer) |
| dbp:chemspiderid | 167141 (xsd:integer) |
| dbp:h | 15 (xsd:integer) |
| dbp:image | 6 (xsd:integer) |
| dbp:iupacName | 1 (xsd:integer) |
| dbp:legalCa | Schedule I (en) |
| dbp:legalDe | NpSG (en) |
| dbp:legalUk | Class B (en) |
| dbp:n | 1 (xsd:integer) |
| dbp:o | 1 (xsd:integer) |
| dbp:pregnancyCategory | ? (en) |
| dbp:pubchem | 192599 (xsd:integer) |
| dbp:routesOfAdministration | Oral (en) |
| dbp:smiles | O2c1ccCCC (en) |
| dbp:stdinchi | 1 (xsd:integer) |
| dbp:stdinchikey | VRNGXHJGMCJRSQ-UHFFFAOYSA-N (en) |
| dbp:unii | O72F3CP4O8 (en) |
| dbp:verifiedfields | changed (en) |
| dbp:verifiedrevid | 477225590 (xsd:integer) |
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| dcterms:subject | dbc:Designer_drugs dbc:Entactogens_and_empathogens dbc:Serotonin-norepinephrine-dopamine_releasing_agents dbc:6-Benzofuranethanamines dbc:Substituted_amphetamines |
| gold:hypernym | dbr:Stimulant |
| rdf:type | owl:Thing dul:ChemicalObject dbo:ChemicalSubstance wikidata:Q8386 yago:WikicatBenzofurans yago:Abstraction100002137 yago:Benzofuran114898101 yago:Chemical114806838 yago:Compound114818238 yago:Material114580897 yago:Matter100020827 yago:Part113809207 yago:PhysicalEntity100001930 yago:Relation100031921 dbo:Drug yago:Substance100019613 |
| rdfs:comment | 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. 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. 5-APDB (3-Desoxy-MDA) is an analogue of 6-APDB where the 3-position oxygen has been replaced with a methylene instead. 6-APDB, along with 5-APDB, was first synthesized by David E. Nichols in the early 1990s while investigating non-neurotoxic MDMA analogues. (en) |
| rdfs:label | 6-APDB (en) |
| owl:sameAs | freebase:6-APDB yago-res:6-APDB wikidata:6-APDB dbpedia-sh:6-APDB dbpedia-sr:6-APDB https://global.dbpedia.org/id/4Ja8S |
| prov:wasDerivedFrom | wikipedia-en:6-APDB?oldid=1084234070&ns=0 |
| foaf:depiction | wiki-commons:Special:FilePath/4-desoxy-MDA.svg wiki-commons:Special:FilePath/6-APDB_molecule_ball.png |
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| is foaf:primaryTopic of | wikipedia-en:6-APDB |
