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Benington F, Morin RD. 
“Enzymatic 5-hydroxylation of 3-methoxytyramine”. 
Experientia. 1968 Jan 10;24(1):33-4.
Abstract
Hydroxylation of phenylalanine to tyrosine x, and subsequently to DOPA -, by oxygenating enzyme systems present in many sources of mammalian tissue, have been demonstrated to be the key initial steps for the biosynthesis of catecholamines 3. The existance of these enzymes and the necessary cofactors have been demonstrated by extensive in vitro and in vivo studiesL The only report of in vivo hydroxylation of a catecholamine to a trihydric phenolic amine was the demonstration by SENOH et al. 5 that 2, 4, 5-trihydroxy-fl-phenethylamine was excreted as a minor labeled urinary metabolite when dopamine-8-C 14 was administered to rats. LEETE ~ showed that tyrosine-8-C xa is converted to mescalin-8-C x4 in the tissues of the cactus Anhalonium lewinii. This is direct evidence for the biological transformation of a monohydric phenol to a completely 0-methylated trihydric phenolic amine by a plant organism. However, further hydroxylation of catecholamines or other dihydric phenols to 3, 4, 5-trihydric phenols has not previously been reported to occur in mammals.
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