Formation of imine derivatives between biologically occurring amines and oxo-steroids

Various biologically occurring amines have been shown to react with 3-oxo-17-oxo and 20-oxo-steroids during solvent evaporation at room temperature to form a complex pattern of products in each case. Using aliphatic monoamines it was shown that imine derivatives are first formed which rapidly rearrange into yet unidentified compounds. The extent of the overall transformation of the oxo-steroid varied with the amine investigated. Thus histamine gave rise to a 95% conversion of 17 beta-hydroxy-4-androsten-3-one (testosterone), whereas epinephrine caused 5% transformation under the same conditions. Imine formation as an experimental error in studies on the biochemistry of steroids is suggested.