19-Nor-5-androstenediol

19-Nor-5-androstenediol, also known as estr-5-ene-3β,17β-diol, 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]

Other namesEstr-5-ene-3β,17β-diol; 19-Norandrost-5-ene-3β,17β-diol

Routes of
administrationBy mouth

CAS Number

• 25975-59-1 ^Y

PubChem CID

• 9900246

Quick facts Clinical data, Other names ...

19-Nor-5-androstenediol

Clinical data
Other names	Estr-5-ene-3β,17β-diol; 19-Norandrost-5-ene-3β,17β-diol
Routes of administration	By mouth
Identifiers
IUPAC name (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	25975-59-1 Y
PubChem CID	9900246
ChemSpider	19967184
UNII	5N0V272KSA
ChEMBL	ChEMBL259126
CompTox Dashboard (EPA)	DTXSID70703096
Chemical and physical data
Formula	C18H28O2
Molar mass	276.420 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@@H]3[C@H]4CC[C@@H](CC4=CC[C@H]3[C@@H]1CC[C@@H]2O)O
InChI 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

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19-Nor-5-androstenediol, 19-nor-5-androstenedione, 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]