19-Nor-5-androstenedione

19-Nor-5-androstenedione, also known as estr-5-ene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) and a derivative of 19-nortestosterone (nandrolone) that was never introduced for medical use.[1][2][3] It is an androgen prohormone of nandrolone and of other 19-norandrostanes.[1][2][3]

19-Nor-5-androstenedione

Clinical data
Other names	Estr-5-ene-3,17-dione; 19-Norandrost-5-ene-3,17-dione
Routes of administration	Oral
Identifiers
IUPAC name (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	19289-77-1
PubChem CID	18633059
ChemSpider	18612511
UNII	585LQ9KZN8
Chemical and physical data
Formula	C18H24O2
Molar mass	272.388 g·mol^−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@@H]3[C@H]4CCC(=O)CC4=CC[C@H]3[C@@H]1CCC2=O
InChI 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, 19-nor-5-androstenediol, and other 19-norandrostane prohormones were considered to be nutritional supplements and were sold over-the-counter in the United States as a result of the Dietary Supplement Health and Education Act of 1994 (DSHEA).[1][2] However, they were banned from sports in 1999 by the International Olympic Committee (IOC) and are currently on the World Anti-Doping Agency (WADA) list of prohibited substances.[1] In 2004, they became controlled substances in the U.S. as a result of the Anabolic Steroid Control Act of 2004.[1]

See also

• 5-Androstenedione
• Bolandiol (19-nor-4-androstenediol)
• Bolandione (19-nor-4-androstenedione)
• Bolenol (17α-ethyl-19-nor-5-androstenol)
• Chlorodehydromethylandrostenediol
• Chloromethylandrostenediol
• Methandriol (17α-methyl-5-androstenediol)

References

1. Torrado 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. doi:10.1002/rcm.3689. PMID 18763272.
2. Uralets 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. Earnest CP (2001). "Dietary androgen 'supplements': separating substance from hype". Phys Sportsmed. 29 (5): 63–79. doi:10.3810/psm.2001.05.781. PMID 20086575.