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19-Nor-5-androstenedione

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19-Nor-5-androstenedione
Clinical data
Other namesEstr-5-ene-3,17-dione; 19-Norandrost-5-ene-3,17-dione
Routes of
administration		Oral
Identifiers
  • (8R,9S,10R,13S,14S)-13-Methyl-1,2,4,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione
CAS Number
PubChemCID
ChemSpider
UNII
Chemical and physical data
FormulaC18H24O2
Molar mass272.388g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@@H]3[C@H]4CCC(=O)CC4=CC[C@H]3[C@@H]1CCC2=O
  • InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,13-16H,3-10H2,1H3/t13-,14+,15+,16-,18-/m0/s1
  • Key:WELNRNVZXWUOGT-QXUSFIETSA-N

19-Nor-5-androstenedione,also known asestr-5-ene-3,17-dione,is asynthetic,orally activeanabolic-androgenic steroid(AAS) and aderivativeof19-nortestosterone(nandrolone) that was never introduced formedical use.[1][2][3]It is anandrogen prohormoneofnandroloneand of other19-norandrostanes.[1][2][3]

19-Nor-5-androstenedione,19-nor-5-androstenediol,and other 19-norandrostane prohormones were considered to benutritional supplementsand were soldover-the-counterin theUnited Statesas a result of theDietary Supplement Health and Education Act of 1994(DSHEA).[1][2]However, they were banned from sports in 1999 by theInternational Olympic Committee(IOC) and are currently on theWorld Anti-Doping Agency(WADA) list of prohibited substances.[1]In 2004, they becamecontrolled substancesin the U.S. as a result of theAnabolic Steroid Control Act of 2004.[1]

See also

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References

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  1. ^abcdeTorrado S, Roig M, Farré M, Segura J, Ventura R (2008). "Urinary metabolic profile of 19-norsteroids in humans: glucuronide and sulphate conjugates after oral administration of 19-nor-4-androstenediol".Rapid Commun. Mass Spectrom.22(19): 3035–42.Bibcode:2008RCMS...22.3035T.doi:10.1002/rcm.3689.PMID18763272.
  2. ^abcUralets VP, Gillette PA (2000)."Over-the-counter delta5 anabolic steroids 5-androsen-3,17-dione; 5-androsten-3beta, 17beta-diol; dehydroepiandrosterone; and 19-nor-5-androsten-3,17-dione: excretion studies in men".J Anal Toxicol.24(3): 188–93.doi:10.1093/jat/24.3.188.PMID10774538.
  3. ^abEarnest CP (2001). "Dietary androgen 'supplements': separating substance from hype".Phys Sportsmed.29(5): 63–79.doi:10.3810/psm.2001.05.781.PMID20086575.S2CID40760529.
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