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14116-06-4Relevant articles and documents
In vitro neuronal and vascular responses to 5-hydroxytryptamine: Modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine
Murphy, James E.J.,Flynn, James J.,Cannon, Dara M.,Guiry, Patrick J.,McCormack, Peter,Baird, Alan W.,McBean, Gethin J.,Keenan, Alan K.
, p. 61 - 67 (2002)
4-Methylthioamphetamine and 4-methylthiomethamphetamine are thioarylethylamines structurally related to 3,4-methylenedioxymethamphetamine (MDMA, 'Ecstasy'). This study compared effects of these agents and MDMA on 5-hydroxytryptamine (5-HT) signalling systems in the brain and vasculature in vitro. Both 4-methylthioamphetamine and 4-methylthiomethamphetamine (100 μM) reduced the rate of specific high affinity [3H]5-HT reuptake in isolated rat brain synaptosomes to 14% and 10% of control, respectively. The concentration required for half-maximal inhibition (IC50) of [3H]5-HT reuptake by 4-methylthioamphetamine (0.27 μM) was significantly lower (P3H]5-HT from synaptosomes, but were significantly less effective than MDMA at the concentrations tested (1-100 μM). In isolated rat aorta, a 15-min preincubation with 4-methylthioamphetamine or 4-methylthiomethamphetamine significantly reduced the maximal contraction (Emax) induced by 5-HT to 71% or 91% of control (P50) from 4.13 to 20.08 μM (Pmax or the EC50 of 5-HT-induced aortic contraction. It is concluded that both 4-methylthioamphetamine and 4-methylthiomethamphetamine are potent inhibitors of [3H]5-HT reuptake in the brain. Furthermore, unlike MDMA, they both directly inhibit 5-HT-mediated vascular contraction. These results suggest that these compounds may be potentially more harmful than MDMA in the context of human misuse.
Synthesis and serotonin transporter activity of sulphur-substituted α-alkyl phenethylamines as a new class of anticancer agents
Cloonan, Suzanne M.,Keating, John J.,Butler, Stephen G.,Knox, Andrew J.S.,Jorgensen, Anne M.,Peters, Guenther H.,Rai, Dilip,Corrigan, Desmond,Lloyd, David G.,Williams, D. Clive,Meegan, Mary J.
scheme or table, p. 4862 - 4888 (2010/01/16)
The discovery that some serotonin reuptake transporter (SERT) ligands have the potential to act as pro-apoptotic agents in the treatment of cancer adds greatly to their diverse pharmacological application. 4-Methylthioamphetamine (MTA) is a selective ligand for SERT over other monoamine transporters. In this study, a novel library of structurally diverse 4-MTA analogues were synthesised with or without N-alkyl and/or C-α methyl or ethyl groups so that their potential SERT-dependent antiproliferative activity could be assessed. Many of the compounds displayed SERT-binding activity as well as cytotoxic activity. While there was no direct correlation between these two effects, a number of derivatives displayed anti-tumour effects in lymphoma, leukaemia and breast cancer cell lines, showing further potential to be developed as possible chemotherapeutic agents.