TY - JOUR T1 - Ethylenedioxy homologs of N-methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA) and its corresponding cathinone analog methylenedioxymethcathinone: Interactions with transporters for serotonin, dopamine, and norepinephrine. AU - Del Bello,Fabio, AU - Sakloth,Farhana, AU - Partilla,John S, AU - Baumann,Michael H, AU - Glennon,Richard A, Y1 - 2015/07/23/ PY - 2015/05/14/received PY - 2015/07/07/revised PY - 2015/07/16/accepted PY - 2015/8/3/entrez PY - 2015/8/4/pubmed PY - 2016/6/21/medline KW - DAT KW - MDMA KW - MDMC KW - NET KW - SERT SP - 5574 EP - 9 JF - Bioorganic & medicinal chemistry JO - Bioorg Med Chem VL - 23 IS - 17 N2 - N-Methyl-(3,4-methylenedioxyphenyl)-2-aminopropane (MDMA; 'Ecstasy'; 1) and its β-keto analog methylone (MDMC; 2) are popular drugs of abuse. Little is known about their ring-expanded ethylenedioxy homologs. Here, we prepared N-methyl-(3,4-ethylenedioxyphenyl)-2-aminopropane (EDMA; 3), both of its optical isomers, and β-keto EDMA (i.e., EDMC; 4) to examine their effects at transporters for serotonin (SERT), dopamine (DAT), and norepinephrine (NET). In general, ring-expansion of the methylenedioxy group led to a several-fold reduction in potency at all three transporters. With respect to EDMA (3), S(+)3 was 6-fold, 50-fold, and 8-fold more potent than its R(-) enantiomer at SERT, DAT, and NET, respectively. Overall, in the absence of a β-carbonyl group, the ethylenedioxy (i.e., 1,4-dioxane) substituent seems better accommodated at SERT than at DAT and NET. SN - 1464-3391 UR - https://www.unboundmedicine.com/medline/citation/26233799/Ethylenedioxy_homologs_of_N_methyl__34_methylenedioxyphenyl__2_aminopropane__MDMA__and_its_corresponding_cathinone_analog_methylenedioxymethcathinone:_Interactions_with_transporters_for_serotonin_dopamine_and_norepinephrine_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0968-0896(15)00619-7 DB - PRIME DP - Unbound Medicine ER -