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 names3α-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
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H28O2
Molar mass276.420 g·mol−1
3D model (JSmol)
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

References
  1. "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.
  2. Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS (2000). "Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite". JAMA. 284 (20): 2618–21. doi:10.1001/jama.284.20.2618. PMID 11086369. Retrieved 29 December 2008.
  3. 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.
  4. Schmitt N, Flament MM, Goubault C, Legros P, Grenier-Loustalot MF, Denjean A (September 2002). "Nandrolone excretion is not increased by exhaustive exercise in trained athletes". Med Sci Sports Exerc. 34 (9): 1436–9. doi:10.1097/00005768-200209000-00006. PMID 12218735.
  5. 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.
  6. 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.
  7. 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.
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