H. Lardy
Nov 1, 1955
Citations
0
Influential Citations
2
Citations
Journal
Endocrinology
Abstract
An investigation of the O-methyl ether of thyroxine was prompted by conflicting evidence in the literature concerning the biological activity of this compound and by the possibility that in vivo methylation of thyroxine is concerned either with the biosynthesis of the cellularly-active form of the hormone or with the detoxication of thyroxine. O-Methyl-DL-thyroxine was first synthesized by Myers (1932) by reaction of N-acetyl thyroxine with dimethyl sulfate. The methyl ether (m. p. 210-213°) obtained on deacetylation was reported to be less active than thyroxine in stimulating amphibian metamorphosis, and inactive when administered intravenously or subcutaneously to human subjects. In contrast, Loeser, Ruland and Trikojus (1938), who prepared 0- methyl-DL-thyroxine (m. p. 226-228°) by direct methylation of thyroxine or thyroxine methyl ester with diazomethane, reported the compound to be more effective than thyroxine in depressing body weight, incKeasing basal metabolic rate, and in decreasing liver glyco...