19-Norandrosterone

Chemical compound vanc changed changed 477209467 (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 19-Norandrosterone.svg skin-invert-image 250 changed ?? 1225-01-0 correct FDA 5W4XKU708V 9548753 correct chemspider 7827676 correct EBI 36412 18 28 2 C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O correct chemspider 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 correct chemspider UOUIARGWRPHDBX-CQZDKXCPSA-N 3α-Hydroxy-5α-estran-17-one; 5α-Estran-3α-ol-17-one 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).http://www.wada-ama.org/rtecontent/document/2007_List_En.pdf THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD The World Anti-Doping Code World Anti-Doping Agency 2009-05-14 https://web.archive.org/web/20090410171528/http://www.wada-ama.org/rtecontent/document/2007_List_En.pdf 10 April 2009 dead Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite JAMA 284 20 2618–21 2000 11086369 10.1001/jama.284.20.2618 http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=11086369 29 December 2008 subscription 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,Le Bizec B, Monteau F, Gaudin I, André F Evidence for the presence of endogenous 19-norandrosterone in human urine J. Chromatogr. B 723 1–2 157–72 February 1999 10080643 10.1016/S0378-4347(98)00541-6 but another study failed to replicate the result.Schmitt N, Flament MM, Goubault C, Legros P, Grenier-Loustalot MF, Denjean A Nandrolone excretion is not increased by exhaustive exercise in trained athletes Med Sci Sports Exerc 34 9 1436–9 September 2002 12218735 10.1097/00005768-200209000-00006 free Concentration also increases in the urine of female athletes during menstruation.Van Eenoo P, Delbeke FT, de Jong FH, De Backer P 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 October 2001 11717005 10.1016/S0960-0760(01)00112-1 19065089 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.Ayotte C Significance of 19-norandrosterone in athletes' urine samples Br J Sports Med 40 Suppl 1 i25–9 July 2006 16799098 10.1136/bjsm.2006.028027 2657496 Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.Le Bizec B, Gaudin I, Monteau F, Andre F, Impens S, De Wasch K, De Brabander H 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 2000 10861987 10.1002/1097-0231(20000630)14:12<1058::AID-RCM991>3.0.CO;2-7 See also Androsterone 19-Noretiocholanolone 5α-Dihydronandrolone 5α-Dihydronorethisterone References External links Testing for 19-norandrosterone Doping Control Procedures Category:5α-Reduced steroid metabolites Category:Secondary alcohols Category:Androgens Category:Estranes Category:Human drug metabolites Category:Ketones