Identification of p-hydroxy-alpha-(methylaminomethyl) benzyl alcohol (synephrine) in human urine.

During the development of an assay for the metanephrines (m 0 -methylepinephrine and m 0 -methylnorepinephrine) in human urine (I), another compound was detected which had similar chemical and chromatographic properties. Like the metanephrines, it was adsorbed onto a weak cation exchange resin, and upon treatment with periodate it yielded a product which absorbed ultraviolet light. The identification of the periodate cleavage product as p-hydroxybenzaldehyde suggested that the unknown base in urine was a derivative of p-hydroxyphenylethanolamine. Further studies by a variety of procedures have definitely established its identity as p-hydroxy-oc-(methylaminomethyl)benzyl alcohol (synephrine, Sympatol),