108536-18-1Relevant articles and documents
Comparative potencies of 3,4-methylenedioxymethamphetamine (MDMA) analogues as inhibitors of [3H]noradrenaline and [3H]5-HT transport in mammalian cell lines
Montgomery,Buon,Eibauer,Guiry,Keenan,McBean
, p. 1121 - 1130 (2007)
Background and purpose: Illegal 'ecstasy' tablets frequently contain 3,4-methylenedioxymethamphetamine (MDMA)-like compounds of unknown pharmacological activity. Since monoamine transporters are one of the primary targets of MDMA action in the brain, a number of MDMA analogues have been tested for their ability to inhibit [3H]noradrenaline uptake into rat PC12 cells expressing the noradrenaline transporter (NET) and [3H]5-HT uptake into HEK293 cells stably transfected with the 5-HT transporter (SERT). Experimental approach: Concentration-response curves for the following compounds at both NET and SERT were determined under saturating substrate conditions: 4-hydroxy-3-methoxyamphetamine (HMA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 3,4-methylenedioxy-N-hydroxyamphetamine (MDOH), 2,5-dimethoxy-4- bromophenylethylamine (2CB), 3,4-dimethoxymethamphetamine (DMMA), 3,4-methylenedioxyphenyl-2-butanamine (BDB), 3,4-methylenedioxyphenyl-N-methyl- 2-butanamine (MBDB) and 2,3-methylenedioxymethamphetamine (2,3-MDMA). Key results: 2,3-MDMA was significantly less potent than MDMA at SERT, but equipotent with MDMA at NET. 2CB and BDB were both significantly less potent than MDMA at NET, but equipotent with MDMA at SERT. MBDB, DMMA, MDOH and the MDMA metabolites HMA and HMMA, were all significantly less potent than MDMA at both NET and SERT. Conclusions and implications: This study provides an important insight into the structural requirements of MDMA analogue affinity at both NET and SERT. It is anticipated that these results will facilitate understanding of the likely pharmacological actions of structural analogues of MDMA.
Synthesis of angular quinoid heterocycles from 2-(2-nitrovinyl)-1,4- benzoquinone
Noland, Wayland E.,Kedrowski, Brant L.
, p. 596 - 603 (1999)
Reactions of 2-(2-nitrovinyl)-1,4-benzoquinone with furans, indoles, and endocyclic enol ethers form angular fused heterocyclic quinoid ring systems. The reaction proceeds by a formal inverse electron-demand [4 + 2] cycloaddition reaction of the nitrovinylquinone and a double bond of the heterocycle. The initial quinoid cycloadducts can be readily tautomerized to hydroquinoid species, which may be dehydrogenated to fully aromatic quinones. In the case of furans, the tautomerized adducts may be ring-opened to give 6,7-di- or 5,6,7-tri-substituted-1,4-naphthalenediols. In the case of endocyclic enol ethers, formation of benzofuran products competes with [4 + 2] cycloaddition.
Synthesis of 25X-BOMes and 25X-NBOHs (X = H, I, Br) for pharmacological studies and as reference standards for forensic purposes
Alves de Barros, Wellington,Queiroz, Marcelo Pereira,da Silva Neto, Leonardo,Borges, Graziele Martins,Martins, Felipe Terra,de Fátima, ?ngelo
supporting information, (2021/01/28)
An expeditious method is reported for the synthesis of three NBOHs (25H-, 25I- and 25B-NBOH; 9–38% overall yield) and three NBOMes (25H-, 25I- and 25B-NBOMe; 7–33% overall yield) from salicylaldehyde and 2-methoxyaldehyde, respectively. The X-ray structures of 25H-, 25I- and 25B-NBOH.HCl were also determined. Our approach should provide a general entry for preparing such a class of substances for pharmacological and forensic purposes.
Immunoassay for Phenethylamines of the 2C and DO Sub-Families
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Page/Page column, (2015/02/19)
Immunoassay methods and their requisite components for the detection and determination of phenethylamines of the 2C and DO sub-families are described.