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6-APDB

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]

6-APDB
Clinical data
Pregnancy
category
  • ?
Routes of
administration
Oral
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-(2,3-dihydro-1-benzofuran-6-yl)propan-2-amine
CAS Number
  • 152623-93-3 N
PubChem CID
  • 192599
ChemSpider
  • 167141 Y
UNII
  • O72F3CP4O8
ChEMBL
  • ChEMBL124055 Y
CompTox Dashboard (EPA)
  • DTXSID60934559
Chemical and physical data
FormulaC11H15NO
Molar mass177.247 g·mol−1
3D model (JSmol)
  • 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
 NY (what is this?)  (verify)

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 edit

  1. ^ 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.
  2. ^ UK Home Office (2014-03-05). "The Misuse of Drugs Act 1971 (Ketamine etc.) (Amendment) Order 2014". UK Government. Retrieved 2014-03-11.

apdb, this, article, needs, additional, citations, verification, please, help, improve, this, article, adding, citations, reliable, sources, unsourced, material, challenged, removed, find, sources, news, newspapers, books, scholar, jstor, november, 2023, learn. This article needs additional citations for verification Please help improve this article by adding citations to reliable sources Unsourced material may be challenged and removed Find sources 6 APDB news newspapers books scholar JSTOR November 2023 Learn how and when to remove this template message 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 6 APDBClinical dataPregnancycategory Routes ofadministrationOralATC codenoneLegal statusLegal statusCA Schedule I DE NpSG Industrial and scientific use only UK Class BIdentifiersIUPAC name 1 2 3 dihydro 1 benzofuran 6 yl propan 2 amineCAS Number152623 93 3 NPubChem CID192599ChemSpider167141 YUNIIO72F3CP4O8ChEMBLChEMBL124055 YCompTox Dashboard EPA DTXSID60934559Chemical and physical dataFormulaC 11H 15N OMolar mass177 247 g mol 13D model JSmol Interactive imageSMILES O2c1cc ccc1CC2 CC N CInChI 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 YKey VRNGXHJGMCJRSQ UHFFFAOYSA N Y N Y what is this verify 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 edit 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 Retrieved from https en wikipedia org w index php title 6 APDB amp oldid 1183767225, wikipedia, wiki, book, books, library,

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