A Biochemical Effect of Deuterium

Abstract

AMONG the naturally occurring steroid hormones and metabolites the androgens are unique in that 3-hydroxy-5α-androstanes exhibit high hormonal activity, the 3α-hydroxy (axial) compounds being highly active while the 3β-hydroxy (equatorial) compounds are much weaker androgens. It is known from both chemical and microbiological work¹ that the 3α-alcohols are oxidized more readily to the corresponding 3-ketone than are the 3β-alcohols, in accordance with the thermodynamic prediction. It is further known that enzymic oxidation of 3-hydroxy-5α-androstanes occurs in mammalian tissue, in particular in the liver. This suggests the possibility that in vivo these compounds are oxidized in various degrees to the even more potent androgens, the 3-keto-5α-androstanes, and that, in fact, the 3-alcohols may be androgenically inactive per se.