Epiandrosterone

Epiandrosterone, or isoandrosterone,^[1][2] also known as 3β-androsterone, 3β-hydroxy-5α-androstan-17-one, or 5α-androstan-3β-ol-17-one, is a steroid hormone with weak androgenic activity. It is a metabolite of testosterone and dihydrotestosterone (DHT). It was first isolated in 1931, by Adolf Friedrich Johann Butenandt and Kurt Tscherning. They distilled over 17,000 litres of male urine, from which they got 50 milligrams of crystalline androsterone (most likely mixed isomers), which was sufficient to find that the chemical formula was very similar to estrone.

Epiandrosterone

Clinical data
ATC code	none
Identifiers
IUPAC name (3S,5S,8R,9S,10S,13S,14S)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,
CAS Number	481-29-8 Y
PubChem CID	441302
ChemSpider	390065 Y
UNII	8TR252Z538
ChEBI	CHEBI:541975 Y
ChEMBL	ChEMBL272195 Y
CompTox Dashboard (EPA)	DTXSID20289698
ECHA InfoCard	100.006.877
Chemical and physical data
Formula	C19H30O2
Molar mass	290.447 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@@H](O)CC[C@]34C)C
InChI InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16-,18-,19-/m0/s1 Y Key:QGXBDMJGAMFCBF-LUJOEAJASA-N Y
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Epiandrosterone has been shown to naturally occur in most mammals including pigs.^[3]

Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA.^{[4][5][6][7][verification needed]} Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.^[8]

See also

• 3β-Androstanediol
• Androstenol
• Androstenone
• Estratetraenol