Methoxydienone

{{Short description|Steroid}}

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| IUPAC_name = (8R,9S,13S,14S)-13-Ethyl-3-methoxy-4,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-one

| image = Methoxydienone.svg

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| routes_of_administration = By mouth

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| CAS_number = 2322-77-2

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| PubChem = 102242

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| ChemSpiderID = 92372

| UNII = 12AU99WIMP

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| synonyms = Methoxygonadiene; 3-Methoxy-17-dehydro-18-methyl-19-nor-δ^2,5(10)-testosterone; 13β-Ethyl-3-methoxygona-2,5(10)-dien-17-one; 18-Methyl-19-nor-δ^2,5(10)-epiandrosterone 3-methyl ether

| C=20 | H=28 | O=2

| SMILES = CC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3CC=C(C4)OC

| StdInChI_Ref =

| StdInChI = 1S/C20H28O2/c1-3-20-11-10-16-15-7-5-14(22-2)12-13(15)4-6-17(16)18(20)8-9-19(20)21/h5,16-18H,3-4,6-12H2,1-2H3/t16-,17-,18+,20+/m1/s1

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| StdInChIKey = PQMRKLSVUBRLLQ-XSYGEPLQSA-N

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{{One source|date=January 2022}}

Methoxydienone, also known as methoxygonadiene, as well as 3-methoxy-17-dehydro-18-methyl-19-nor-δ^2,5(10)-testosterone or 13β-ethyl-3-methoxygona-2,5(10)-dien-17-one, is a synthetic anabolic-androgenic steroid (AAS) and progestogen of the 19-nortestosterone group related to levonorgestrel which was never marketed.{{cite journal | vauthors = Rahnema CD, Crosnoe LE, Kim ED | title = Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem | journal = Andrology | volume = 3 | issue = 2 | pages = 150–5 | year = 2015 | pmid = 25684733 | doi = 10.1111/andr.307 | s2cid = 6999218 | doi-access = free }} It was synthesized in the 1960s and 1970s by chemist Herchel Smith and his colleagues while they were developing progestins for use in oral contraceptives. The drug is a potent anabolic when administered via injection with an anabolic:androgenic ratio of approximately 54:27 relative to testosterone propionate and 90:625 relative to nandrolone. Methoxydienone is not 17α-alkylated (instead featuring a ketone at the C17 position) and no data exist regarding its oral activity in humans. It has been sold on the Internet as a designer steroid.