Bolandiol

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.^[1] However, a dipropionate ester derivative, bolandiol dipropionate, has been marketed.^[1][2] Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses estrogenic and progestogenic activity.^[3][4]

Other names19-Norandrostenediol; 19-Nor-4-androstene-3β,17β-diol; Estr-4-ene-3β,17β-diol; 3β-Dihydronandrolone

CAS Number

• 19793-20-5

PubChem CID

• 9835303

ChemSpider

• 8011024

Quick facts Clinical data, Other names ...

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

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Bolandiol is on the World Anti-Doping Agency's list of prohibited substances,^[5] 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).^[6] However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.^[7][8]