6-APDB

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6-APDB
4-desoxy-MDA.svg
6-APDB molecule ball.png
Clinical data
Routes of
administration 		By mouth
Drug class Empathogen–entactogen; Stimulant
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H15NO
Molar mass 177.247 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 Yes check.svgY
  • Key:VRNGXHJGMCJRSQ-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

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]

Contents

Pharmacology

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. [2]

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. [3]

Chemistry

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.

Society and culture

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. [4]

References

  1. 1 2 3 4 5 6 7 8 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.
  2. ↑ Rickli A, Kopf S, Hoener MC, Liechti ME (July 2015). "Pharmacological profile of novel psychoactive benzofurans". Br J Pharmacol. 172 (13): 3412–3425. doi:10.1111/bph.13128. PMC   4500375 . PMID   25765500.
  3. ↑ Dolan SB, Forster MJ, Gatch MB (November 2017). "Discriminative stimulus and locomotor effects of para-substituted and benzofuran analogs of amphetamine". Drug Alcohol Depend. 180: 39–45. doi:10.1016/j.drugalcdep.2017.07.041. PMC   6463889 . PMID   28865391.
  4. ↑ 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. Retrieved 2014-03-11.
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