Conde S, Madroñero R, Fernández-Tomé M P, del Río J
J Med Chem. 1978 Sep;21(9):978-81. doi: 10.1021/jm00207a024.
Ring-chlorinated thienylisopropylamines, thiophene analogues of chloroamphetamines, have been synthesized and their effects on serotonergic mechanisms in the rat brain have been evaluated. With 4,5-dichlorothienylisopropylamine (3e), a pharmacological profile similar to that of p-chloroamphetamine, consisting in a marked and long-lasting serotonin depletion and a rather strong and prolonged inhibition of synaptosomal uptake of serotonin, was found. Chloro substitution in position C3 of the thiophene ring did not determine brain serotonin depletion nor serotonin uptake inhibition but enhanced brain MAO inhibitory activity present in all these compounds. 3,5-Dichlorothienylisopropylamine (3g) was the only compound of the series in which the inhibition of serotonin uptake was more marked than the serotonin depleting property.
环氯化噻吩基异丙胺，即氯苯丙胺的噻吩类似物，已被合成，并评估了它们对大鼠脑内5-羟色胺能机制的影响。对于4,5-二氯噻吩基异丙胺（3e），发现其药理学特征与对氯苯丙胺相似，包括显著且持久的5-羟色胺耗竭以及对突触体摄取5-羟色胺相当强烈且持久的抑制。噻吩环C3位的氯取代既未导致脑内5-羟色胺耗竭，也未抑制5-羟色胺摄取，但增强了所有这些化合物中存在的脑单胺氧化酶抑制活性。3,5-二氯噻吩基异丙胺（3g）是该系列中唯一一种对5-羟色胺摄取的抑制比对5-羟色胺耗竭特性更显著的化合物。
