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{{Short description|Steroid}}
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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<sup>2,5(10)</sup>-testosterone''' or '''13β-ethyl-3-methoxygona-2,5(10)-dien-17-one''', is a [[synthetic compound|synthetic]] [[anabolic-androgenic steroid]] (AAS) and [[progestogen]] of the [[19-nortestosterone]] group related to [[levonorgestrel]] which was never marketed.<ref name="pmid25684733">{{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 }}</ref> It was [[chemical synthesis|synthesized]] in the 1960s and 1970s by [[chemist]] [[Herchel Smith]] and his colleagues while they were developing [[progestin]]s for use in [[oral contraceptive]]s.<ref name="pmid25684733" /> The drug is a potent [[anabolic]] when administered via [[injection (medicine)|injection]] with an [[anabolic:androgenic ratio]] of approximately 54:27 relative to [[testosterone propionate]] and 90:625 relative to [[nandrolone]].<ref name="pmid25684733" /> Methoxydienone is not [[17α-alkylated anabolic steroid|17α-alkylated]] (instead featuring a [[ketone]] at the C17 position) and no data exist regarding its [[oral administration|oral activity]] in humans.<ref name="pmid25684733" /> It has been sold on the [[Internet]] as a [[designer steroid]].<ref name="pmid25684733" />
'''Methoxydienone''', also known as '''methoxygonadiene''', as well as '''3-methoxy-17-dehydro-18-methyl-19-nor-δ<sup>2,5(10)</sup>-testosterone''' or '''13β-ethyl-3-methoxygona-2,5(10)-dien-17-one''', is a [[synthetic compound|synthetic]] [[anabolic-androgenic steroid]] (AAS) and [[progestogen]] of the [[19-nortestosterone]] group related to [[levonorgestrel]] which was never marketed.<ref name="pmid25684733">{{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 }}</ref> It was [[chemical synthesis|synthesized]] in the 1960s and 1970s by [[chemist]] [[Herchel Smith]] and his colleagues while they were developing [[progestin]]s for use in [[oral contraceptive]]s.<ref name="pmid25684733" /> The drug is a potent [[anabolic]] when administered via [[injection (medicine)|injection]] with an [[anabolic:androgenic ratio]] of approximately 54:27 relative to [[testosterone propionate]] and 90:625 relative to [[nandrolone]].<ref name="pmid25684733" /> Methoxydienone is not [[17α-alkylated anabolic steroid|17α-alkylated]] (instead featuring a [[ketone]] at the C17 position) and no data exist regarding its [[oral administration|oral activity]] in humans.<ref name="pmid25684733" /> It has been sold on the [[Internet]] as a [[designer steroid]].<ref name="pmid25684733" />


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Latest revision as of 17:46, 11 November 2023

Methoxydienone
Clinical data
Other namesMethoxygonadiene; 3-Methoxy-17-dehydro-18-methyl-19-nor-δ2,5(10)-testosterone; 13β-Ethyl-3-methoxygona-2,5(10)-dien-17-one; 18-Methyl-19-nor-δ2,5(10)-epiandrosterone 3-methyl ether
Routes of
administration		By mouth
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC20H28O2
Molar mass300.442 g·mol−1
3D model (JSmol)
  • CC[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)CCC4=C3CC=C(C4)OC
  • InChI=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
  • Key:PQMRKLSVUBRLLQ-XSYGEPLQSA-N

Methoxydienone, also known as methoxygonadiene, as well as 3-methoxy-17-dehydro-18-methyl-19-nor-δ2,5(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.[1] 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.[1] 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.[1] Methoxydienone is not 17α-alkylated (instead featuring a ketone at the C17 position) and no data exist regarding its oral activity in humans.[1] It has been sold on the Internet as a designer steroid.[1]

See also

[edit]

References

[edit]
  1. ^ a b c d e Rahnema CD, Crosnoe LE, Kim ED (2015). "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–5. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.



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