The synthesis of deuterated hydroxyphenylethanolamines and their metabolites

Abstract

SUMMARYThe 0-, m-and p-NC r2H3] synephrines were prepared via a three step reaction from the corresponding oxazolidones. King deuterated ms nephrine, m-octopamine and m-hydroxymandelic acid were prepared byReduction of 0-and m-mandelic acid with lithium aluminum deuteride afforded the corresponding hydroxyphenylglycols. Exclusive side chain deuteration of 2-dibenzyl-l-(4-hydroxyphenyl)ethanone and 2-methylamino-l-(3,4-dihydroxypheny1)ethanone were accomplished in both acidic and basic media. The former compound was deuterated on both t h e side chain and aromatic ring using 45% [2H1]Br.

Quantitative measurement of octopamines and synephrines in urine using capillary column gas chromatography negative ion chemical ionization mass spectrometry

“…Reagents. These were obtained from the following sources: pentafluoropropionic anhydride (PFPA), Pierce Chemical Co. Other compounds were synthesized as previously described in the literature: o-octopamine (13), o-synephrine benzoate (-d0 and methyl-d3) (14), o-tyramine (15), m-octopamine-2,4,6-d3 hydrochloride ( 16), m-synephrine-2,4,6-d3 hydrochloride (16), p-synephrine (methyl-d3) ( 16), p-octopamine-a,a'-d2-3,5-d2 hydrochloride (16), and IV-methylphenylethanolamine (17).…”

“…(±0.2), 2.1 (±0.8), 25 (±19), ÑD (<0.1), 1.8 (±0.7), and 16 (±10) ng mg'1 creatinine. The occurrence of o-and m-octopamlne and m-synephrlne In human tissue or fluid has not been reported previously.…”