5-APDB

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5-APDB
3-desoxy-MDA.svg
Systematic (IUPAC) name
1-(2,3-dihydro-1-benzofuran-5-yl)propan-2-amine
Clinical data
Pregnancy cat. ?
Legal status Uncontrolled (but may be covered under the Federal Analogue Act in the United States and under similar bills in other countries)
Routes Oral
Identifiers
CAS number 152624-03-8 N
ATC code None
PubChem CID 192601
ChemSpider 167143 N
Chemical data
Formula C11H15NO 
Mol. mass 177.242 g/mol
 N (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classes.[1] It is an analogue of MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene bridge.[1] 6-APDB is an analogue of 5-APDB where the 4-position oxygen has been replaced by a methylene bridge instead.[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic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]

On June 10, 2013 5-APDB and a number of analogues were classified as Temporary Class Drugs in the UK following an ACMD recommendation.[4] This means that sale and import of the named substances are criminal offences and are treated as for class B drugs.[5]


See also[edit]

References[edit]

  1. ^ a b c d e f g 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. ^ Nichols, DE; Hoffman, AJ; Oberlender, RA; Riggs, RM (1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats.". Journal of Medical Chemistry 29 (2): 302–4. doi:10.1021/jm00152a022. PMID 3950910. 
  3. ^ Nichols, DE; Snyder, SE; Oberlender, R; Johnson, MP; Huang, XM (1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines.". Journal of Medical Chemistry 34 (1): 276–81. doi:10.1021/jm00105a043. PMID 1992127. 
  4. ^ "Temporary class drug order report on 5-6APB and NBOMe compounds". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13. 
  5. ^ "'NBOMe' and 'Benzofury' banned". UK Home Office. 4 Jun 2013. Retrieved 2013-06-13.