5-APDB

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5-APDB
File:3-desoxy-MDA.svg
Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-amine
Clinical data
Pregnancy
category
  •  ?
Legal status
Routes of
administration		 Oral
Identifiers
CAS Number 152624-03-8 N
ATC code none
PubChem CID: 192601
ChemSpider 167143 N
UNII UI10BAJ8SH YesY
Chemical data
Formula C11H15NO
Molecular mass 177.242 g/mol
  • Cl.CC(N)Cc1cc2CCOc2cc1
  • InChI=1S/C11H15NO.ClH/c1-8(12)6-9-2-3-11-10(7-9)4-5-13-11;/h2-3,7-8H,4-6,12H2,1H3;1H YesY
  • Key:BZKLFXQUBIRXAK-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA, EMA-4) is a putative entactogen drug of the phenethylamine and amphetamine classes.[1] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[1] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDMA.[1]

In animal studies, 5-APDB's effects generalize most closely to non-stimulant MDMA analogues such as MBDB and MMAI, while producing no substitution for LSD or amphetamine.[1] In vitro studies show that 5-APDB acts as a highly selective serotonin releasing agent (SSRA), with IC50 values of 130 nM, 7,089 nM, and 3,238 nM for inhibiting the reuptake of serotonin, dopamine, and norepinephrine, respectively.[1] In contrast, 6-APDB is more balanced on the three monoamine neurotransmitters and acts more similarly to MDA and MDMA.[1] Anecdotal reports from human users suggest that 5-APDB produces mild empathy but with relatively little euphoria and is accompanied by sedation.[citation needed]

Methoxy-substituted analogues of 5-APDB and 6-APDB have also been made and substituted for DOM in animal tests, although they were around 10x less potent than DOM.[2][3]

Legal Status

China

As of October 2015 5-APDB is a controlled substance in China.[4]

UK

On June 10, 2013 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[5] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[6]

See also

References

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