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6-APDB

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Stimulant designer drug
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Pharmaceutical compound
6-APDB
Ball-and-stick model of the 6-APDB molecule
Clinical data
Routes of
administration
By mouth
Drug classEmpathogen–entactogen;Stimulant
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

6-(2-Aminopropyl)-2,3-dihydrobenzofuran (6-APDB,4-Desoxy-MDA,EMA-3) is astimulant andentactogendrug of thephenethylamine andamphetamine classes.[1] It is ananalogue ofMDA where theheterocyclic 4-positionoxygen from the 3,4-methylenedioxyring has been replaced with amethylene 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 firstsynthesized byDavid E. Nichols in the early 1990s while investigating non-neurotoxicMDMAanalogues.[1]

In animal studies, 6-APDB fully substitutes forMBDB andMMAI but not foramphetamine orLSD.[1]In vitro, 6-APDB has been shown toinhibit thereuptake ofserotonin,dopamine, andnorepinephrine withIC50 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 thecatecholamines 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 itsin vitro profile it can be suggested that it may have amphetamine-like effects at higher doses.

The unsaturated benzofuran derivative6-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

[edit]
  1. ^abcdefghMonte 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.
  2. ^UK Home Office (2014-03-05)."The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government.Archived from the original on 2014-12-04. Retrieved2014-03-11.
Phenylalkyl-
amines

(other than
cathinones)
Cyclizedphenyl-
alkylamines
Cathinones
Tryptamines
Chemical classes
DRAsTooltip Dopamine releasing agents
NRAsTooltip Norepinephrine releasing agents
SRAsTooltip Serotonin releasing agents
Others
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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