19-Norandrosterone

19-Norandrosterone, also known as 5α-estran-3α-ol-17-one, is a metabolite of nandrolone (19-nortestosterone) and bolandione (19-norandrostenedione) that is formed by 5α-reductase. It is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone, an anabolic-androgenic steroid (AAS).^[1] Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.^[2]

19-Norandrosterone

Clinical data
Other names	3α-Hydroxy-5α-estran-17-one; 5α-Estran-3α-ol-17-one
Identifiers
IUPAC name (3R,5S,8R,9R,10S,13S,14S)-3-Hydroxy-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-one
CAS Number	1225-01-0 N
PubChem CID	9548753
ChemSpider	7827676 Y
UNII	5W4XKU708V
ChEBI	CHEBI:36412 Y
CompTox Dashboard (EPA)	DTXSID10893662
Chemical and physical data
Formula	C18H28O2
Molar mass	276.420 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O
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/h11-16,19H,2-10H2,1H3/t11-,12+,13-,14+,15+,16-,18-/m0/s1 Y Key:UOUIARGWRPHDBX-CQZDKXCPSA-N Y
NY (what is this?)  (verify)

Traces of 19-norandrosterone may be naturally present in human urine. An experiment conducted on athletes showed that after a prolonged intense effort, the 19-norandrosterone concentration can be increased by a factor varying between 2 and 4,^[3] but another study failed to replicate the result.^[4] Concentration also increases in the urine of female athletes during menstruation.^[5] The consumption of edible parts of a non-castrated pig, containing 19-nortestosterone, has been shown to result in the excretion of 19-norandrosterone in the following hours, so athletes should prudently avoid meals composed of pig offal in the hours preceding doping tests.^[6] Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.^[7]

See also

• Androsterone
• 19-Noretiocholanolone
• 5α-Dihydronandrolone
• 5α-Dihydronorethisterone