5α-Dihydronandrolone

5α-Dihydronandrolone
Synonyms	5α-DHN; 5α-Dihydro-19-nortestosterone; 5α-Dihydro-19-norandrostenolone
Chemical nomenclature
IUPAC name	(5α,17β)-17-Hydroxyestr-4-en-3-one
Identifiers
CAS Number	434-22-0
PubChem	123057
ChemSpider	109678
Chemical data
Chemical formula	C18H28O2
SMILES	C[C@]12CC[C@H]3[C@@H](CC[C@@]4([C@H]3CC[C@@H]4[C@@H]1CCC2=O)C)O

5α-Dihydronandrolone (5α-DHN) is an androgen and anabolic steroid (AAS) that is a metabolite of nandrolone (19-nortestosterone). It is formed from nandrolone by the action of the enzyme 5α-reductase.

Biological activity

5α-Dihydronandrolone is known to have a lower affinity for the androgen receptor compared to nandrolone. This reduced affinity results in a lower androgenic activity, which is a characteristic of 5α-reduced metabolites of anabolic steroids. The conversion of nandrolone to 5α-DHN occurs primarily in tissues that express 5α-reductase, such as the prostate gland, skin, and hair follicles.

Metabolism

The enzyme 5α-reductase is responsible for the conversion of nandrolone to 5α-DHN. This enzyme is also involved in the conversion of testosterone to dihydrotestosterone (DHT), another potent androgen. The activity of 5α-reductase can influence the overall androgenic effects of nandrolone in the body.

Clinical significance

The reduced androgenic activity of 5α-DHN compared to nandrolone may have clinical implications. For instance, nandrolone is often used in the treatment of conditions such as anemia and osteoporosis due to its anabolic effects. The formation of 5α-DHN may reduce the risk of androgenic side effects, such as acne, hirsutism, and prostate enlargement.

See also

• Nandrolone
• 5α-Reductase
• Androgen receptor
• Anabolic steroid