5α-Dihydronandrolone

5α-Dihydronandrolone
Identifiers

IUPAC name (5S,8R,9R,10S,13S,14S,17S)-17-Hydroxy-13-methyl-2,4,5,6,7,8,9,10,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-one
Synonyms	Dihydronandrolone; DHN; 5α-DHN; 5α-Dihydro-19-nortestosterone; 5α-Estran-17β-ol-3-one; 19-nor-5α-androstan-17β-ol-3-one
CAS Number	1434-85-1
PubChem (CID)	94202
ChemSpider	85015
UNII	I0V6O3097Q
ChEMBL	CHEMBL3137999
Chemical and physical data
Formula	C₁₈H₂₈O₂
Molar mass	276.42 g/mol
3D model (Jmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CC[C@@H]4[C@@H]3CCC(=O)C4
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/h11,13-17,20H,2-10H2,1H3/t11-,13-,14+,15+,16-,17-,18-/m0/s1 Key:RHVBIEJVJWNXBU-PNOKGRBDSA-N

5α-Dihydronandrolone (5α-DHN), or simply as dihydronandrolone (DHN), also known as 5α-dihydro-19-nortestosterone or as 5α-estran-17β-ol-3-one, is a synthetic anabolic-androgenic steroid (AAS) and a 5α-reduced derivative of 19-nortestosterone (nandrolone). It is a major metabolite of nandrolone and is formed from it by the actions of the enzyme 5α-reductase analogously to the formation of dihydrotestosterone (DHT) from testosterone.

When testosterone is 5α-reduced into DHT, which is a much more potent AAS in comparison, its effects are potentiated on a local level. The tissues in which this occurs (i.e., the tissues that express 5α-reductase) are referred to as "androgenic" tissues and include the skin, hair follicles, and prostate gland, among others. The conversion of testosterone into DHT is an important factor in the etiology of a variety of androgen-dependent conditions, including acne, hirsutism, androgenic alopecia, benign prostatic hyperplasia, and prostate cancer. Unlike the case of testosterone and DHT, 5α-DHN is a much weaker agonist of the androgen receptor (AR) than is nandrolone. For this reason, instead of local potentiation in androgenic tissues, there is a local suppression in AR activation when nandrolone is converted into 5α-DHN by 5α-reductase in these tissues. This is largely or completely responsible for the exceptionally high ratio of anabolic to androgenic effects seen with nandrolone.

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