5-apdb Information

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classes.^[1] It is an analogue of the MDA where the heterocyclic 3-position oxygen from the 3,4-methylenedioxy ring has been replaced by a methylene group.^[1] 6-APDB is an anlogue of 5-APDB where the 4-position oxygen has been replaced by a methylene instead.^[1] 5-APDB was developed by a team led by David E. Nichols at Purdue University as part of their research into non-neurotoxic analogues of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.

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]

See also

• 5-APB
• 6-APB
• 6-APDB
• 5-(2-Aminopropyl)indole
• Ethylenedioxymethamphetamine
• Indanylaminopropane
• Naphthylaminopropane
• Tetralinylaminopropane

References

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 medicinal 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 medicinal chemistry 34 (1): 276–81. doi:10.1021/jm00105a043. PMID 1992127.

Categories:

• Psychedelic phenethylamines
• Entactogens and Empathogens
• Benzofurans

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