19-Noretiocholanolone

19-Noretiocholanolone, also known as 5β-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]

19-Noretiocholanolone

Clinical data
Other names	Noretiocholanolone; 5β-Estran-3α-ol-17-one; 3α-Hydroxy-5β-estran-17-one
Identifiers
IUPAC name (3R,5R,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	33036-33-8
PubChem CID	14009228
ChemSpider	19347817
UNII	O5Z6602I6U
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+/m1/s1 Key:UOUIARGWRPHDBX-DHMVHTBWSA-N

Traces of 19-noretiocholanolone may be naturally present in human urine.^{[citation needed]} Consumption of boar meat, liver, kidneys and heart have been found to increase urinary 19-noretiocholanolone output.^[2]

See also

• Etiocholanolone
• 19-Norandrosterone
• 5α-Dihydronandrolone
• 5α-Dihydronorethisterone

References

1. (PDF). The World Anti-Doping Code. World Anti-Doping Agency. Archived from the original (PDF) on 10 April 2009. Retrieved 2009-05-14.
2. Le Bizec B, Gaudin I, Monteau F, Andre F, Impens S, De Wasch K, De Brabander H (2000). "Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. I. Mass spectrometric detection and quantification of 19-norandrosterone and 19-noretiocholanolone in human urine". Rapid Commun. Mass Spectrom. 14 (12): 1058–65. doi:10.1002/1097-0231(20000630)14:12<1058::AID-RCM991>3.0.CO;2-7. PMID 10861987.