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19-Nor-5-androstenediol

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
19-Nor-5-androstenediol
Clinical data
Other namesEstr-5-ene-3β,17β-diol; 19-Norandrost-5-ene-3β,17β-diol
Routes of
administration
By mouth
Identifiers
  • (3S,8R,9S,10R,13S,14S,17S)-13-Methyl-1,2,3,4,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H28O2
Molar mass276.420 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CC[C@@H]2O)O
  • InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h2,12-17,19-20H,3-10H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1
  • Key:VVUQRXPUVKXAIO-XFUVECHXSA-N

19-Nor-5-androstenediol, also known asestr-5-ene-3β,17β-diol, is asynthetic,orally activeanabolic-androgenic steroid (AAS) and aderivative of19-nortestosterone (nandrolone) that was never introduced formedical use.[1][2][3] It is anandrogen prohormone ofnandrolone and of other19-norandrostanes.[1][2][3]

19-Nor-5-androstenediol,19-nor-5-androstenedione, and other 19-norandrostane prohormones were considered to benutritional supplements and were soldover-the-counter in theUnited States as 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 substances in the U.S. as a result of theAnabolic Steroid Control Act of 2004.[1]

See also

[edit]

References

[edit]
  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.PMID 18763272.
  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.PMID 10774538.
  3. ^abEarnest CP (2001). "Dietary androgen 'supplements': separating substance from hype".Phys Sportsmed.29 (5):63–79.doi:10.3810/psm.2001.05.781.PMID 20086575.S2CID 40760529.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

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