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5-(2-Aminopropyl)-2,3-dihydrobenzofuran
Systematic (IUPAC) name
5-(2-Aminopropyl)-2,3-dihydrobenzofuran
Identifiers
CAS number 152623-94-4
ATC code  ?
PubChem 192601
ChemSpider 21073073
Chemical data
Formula C 11H15NO 
Mol. mass 177.242 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes  ?

5-(2-Aminopropyl)-2,3-dihydrobenzofuran (5-APDB, 3-Desoxy-MDA (3D), EMA-4) is an analogue of the entactogen MDA where the heterocyclic 3-position oxygen from the methylenedioxy ring has been replaced by a methylene (CH2) group. It was developed by the team led by David Nichols at Purdue University as part of their research into non-neurotoxic analogues of MDA and MDMA. In animal studies its effects generalise most closely to non-stimulant MDMA analogues such as MBDB and MMAI,[1] and anecdotal reports from human users suggest that it has mild entactogenic effects but accompanied by sedation, with relatively little euphoria. The alternative structural isomer 4-desoxy-MDA ("4D") is also known, and has similar effects in both animals and humans.

4-desoxy-MDA
CAS# 152623-93-3

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

See also

References

  1. ^ Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE. Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine. Journal of Medicinal Chemistry. 1993 Nov 12;36(23):3700-6. PMID 8246240
  2. ^ Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM. 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 Medicinal Chemistry. 1986 Feb;29(2):302-4. PMID 3950910
  3. ^ Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM. 2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines. Journal of Medicinal Chemistry. 1991 Jan;34(1):276-81. PMID 1992127
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