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). Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.
|Other names||3α-Hydroxy-5α-estran-17-one; 5α-Estran-3α-ol-17-one|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||276.420 g·mol−1|
|3D model (JSmol)|
|(what is this?)|
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, but another study failed to replicate the result. Concentration also increases in the urine of female athletes during menstruation. 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. Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.
- "THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD" (PDF). The World Anti-Doping Code. World Anti-Doping Agency. Archived from the original (PDF) on 10 April 2009. Retrieved 2009-05-14.
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- Le Bizec B, Monteau F, Gaudin I, André F (February 1999). "Evidence for the presence of endogenous 19-norandrosterone in human urine". J. Chromatogr. B. 723 (1–2): 157–72. doi:10.1016/S0378-4347(98)00541-6. PMID 10080643.
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- Van Eenoo P, Delbeke FT, de Jong FH, De Backer P (October 2001). "Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen". J. Steroid Biochem. Mol. Biol. 78 (4): 351–7. doi:10.1016/S0960-0760(01)00112-1. PMID 11717005. S2CID 19065089.
- Ayotte C (July 2006). "Significance of 19‐norandrosterone in athletes' urine samples". Br J Sports Med. 40 Suppl 1 (Suppl 1): i25–9. doi:10.1136/bjsm.2006.028027. PMC 2657496. PMID 16799098.
- 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.