The Structure and Function of Oestrogens. VII The Use of (9,12,12-2H3)- and (11x,12,12-2H3) Oestradiol in a Test of the Quinone Methide Hypothesis for Oestrogen Action

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Abstract
Ovariectomized mice were injected intravaginally with a physiological dose of (9,12,12-2H3)estradiol and a control group was similarly injected with (11.xi.,12,12-2H3)estradiol. GLC/mass spectrometry (GLC/MS) analysis of the estradiols recovered from the vagina of the 2 sets of mice showed that the content and distribution of 2H were the same as in the respective pure trideuterated estradiols. This proved conclusively that the 9.alpha.-hydrogen of estradiol is not exchanged during residence in and stimulation of the vagina. It therefore appears unlikely that reversible quinone methide formation in estradiol is the trigger mechanism for stimulation of RNA synthesis, unless a H transfer relay system permits repetitive removal and replacement of the hydrogen atom at C9 during the oxidation-reduction cycle.

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