Zweig J S, Castagnoli N
J Med Chem. 1977 Mar;20(3):414-21. doi: 10.1021/jm00213a020.
The possible relationship between metabolism and psychotomimetic activity among the methoxylated 1-phenyl-2-aminopropanes led to our investigation of the in vitro O-demethylation of 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (1, DOM, STP). Employing a sensitive and highly selective stable isotope dilution assay, we observed that rabbit liver homogenates biotransform the amine 1 to its 2-O-demethyl, 5-O-demethyl, and bis (O-demethyl) metabolite metabolites. Both monophenolic metabolites are enriched in their S enantiomers. The bis(O-demethyl) metabolite has structural, chemical, and electrochemical similarites to the sympatholytic agent "6-hydroxydopamine". The possible significance of metabolic O-demethylation in terms of the psychotomimetic properties of amine 1 is discussed.
甲氧基化的1-苯基-2-氨基丙烷的代谢与拟精神病活性之间的可能关系促使我们对1-(2,5-二甲氧基-4-甲基苯基)-2-氨基丙烷（1，DOM，STP）进行体外O-去甲基化研究。采用灵敏且高度选择性的稳定同位素稀释分析法，我们观察到兔肝匀浆可将胺1生物转化为其2-O-去甲基、5-O-去甲基和双（O-去甲基）代谢物。两种单酚代谢物的S对映体均富集。双（O-去甲基）代谢物在结构、化学和电化学方面与抗交感神经药“6-羟基多巴胺”相似。本文讨论了代谢性O-去甲基化对于胺1拟精神病特性的可能意义。
