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]