Bolandiol

Bolandiol
Clinical data
Other names	19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone
Identifiers
	IUPAC name (3S,8R,9S,10R,13S,14S,17S)-13-methyl-1,2,3,6,7,8,9,10,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,17-diol;
CAS Number	19793-20-5;
PubChem CID	9835303;
ChemSpider	8011024;
UNII	49SD6G16U5;
ChEBI	CHEBI:145661;
ChEMBL	ChEMBL2106664;
CompTox Dashboard (EPA)	DTXSID9041027 ;
Chemical and physical data
Formula	C18H28O2
Molar mass	276.420 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O[C@@H]4/C=C2\[C@@H]([C@H]1CC[C@@]3([C@@H](O)CC[C@H]3[C@@H]1CC2)C)CC4;
	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/h10,12-17,19-20H,2-9H2,1H3/t12-,13-,14+,15+,16-,17-,18-/m0/s1; Key:CMXKUJNZWYTFJN-XFUVECHXSA-N;

Bolandiol (INN, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an anabolic-androgenic steroid (AAS) that was never marketed. However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.

Bolandiol is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports. It is a potential metabolic precursor (via 3β-HSD) to nandrolone or a derivative of nandrolone (via 3β-hydroxy-steroid:NADP⁺ 3-oxidoreductase). However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.