Dimethylstilbestrol (DMS) is a nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was never marketed. It is a so-called "weak", "impeded", or "short-acting" estrogen similarly to estriol and meso-butoestrol. The affinity of DMS for the ER was reported as about 10% of that of estradiol. For comparison, diethylstilbestrol had 140% of the affinity of estradiol for the ER.
The endometrial proliferation dose of DMS in women is 20 mg. A single 12 mg intramuscular injection of DMS has a duration of approximately 12 days in humans.
Synthesis The synthesis begins with the reaction of diacetyl with phenol to yield 2,2-bis(p-hydroxy-m-toluyl)-3-butanone. Pinacol rearrangement then produces the corresponding stilbenoid.
If m-cresol is used as a starting material instead of phenol, the resulting product has a potency 0.5 times the potency of diethylstilbestrol.
In the newer version of the synthesis, a McMurry reaction (homodimerization) between on acetanisole and the appropriate choice of a reagent will yield 1,1'-(but-2-ene-2,3-diyl)bis(4-methoxybenzene). Demethylation of the two ethers then concludes the synthesis.
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