Dimethylstilbestrol
Chemical compound
From Wikipedia, the free encyclopedia
Dimethylstilbestrol (DMS) is a nonsteroidal estrogen of the stilbestrol group related to diethylstilbestrol which was never marketed.[1][2][3][4][5]: 213 It is a so-called "weak", "impeded", or "short-acting" estrogen similarly to estriol and meso-butoestrol.[6][7][8][9] The affinity of DMS for the ER was reported as about 10% of that of estradiol.[10] For comparison, diethylstilbestrol had 140% of the affinity of estradiol for the ER.[10]
- 552-80-7
13366-36-4
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| Other names | DMS; (Ε)-α,α'-Dimethyl-4,4'-stilbenediol |
| Drug class | Nonsteroidal estrogen |
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| Formula | C16H16O2 |
| Molar mass | 240.302 g·mol−1 |
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The endometrial proliferation dose of DMS in women is 20 mg.[5]: 212–213 A single 12 mg intramuscular injection of DMS has a duration of approximately 12 days in humans.[5]
Synthesis
In the old school synthesis, reaction of diacetyl with 2 molecules of phenol occurs in a manner similar to BPA (acetone was used here). Pinacol rearrangement then yields the stilbenoid. What is surprising is that if m-cresol was used instead of phenol, the resulting product had a potency 0.5 times the potency of DES, which is remarkably potent.[11]
In the newer version of the synthesis, a McMurry reaction (homodimerization) between on 4-Acetylanisole [100-06-1] and the appropriate choice of a reagent will yield 1,1'-(But-2-ene-2,3-diyl)bis(4-methoxybenzene) [895-37-4]. Demethylation of the two ethers then concludes the synthesis.[12][13]
