19-Norandrosterone
 | |
| Names | |
|---|---|
| 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 | |
| Identifiers | |
1225-01-0  | |
| ChEBI | CHEBI:36412  |
| ChemSpider | 7827676 |
| Jmol interactive 3D | Image Image |
| PubChem | 9548753 |
| |
| |
| Properties | |
| C18H28O2 | |
| Molar mass | 276.41 g/mol |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| verify (what is ?) | |
| Infobox references | |
19-Norandrosterone is a nandrolone and 19-norandrostenedione metabolite. It is created as a byproduct of nandrolone via the 5-alpha reductase enzyme and is on the list of substances prohibited by the World Anti-Doping Agency since it is a detectable metabolite of nandrolone which is an anabolic steroid.[1] Consumption of androstendione products contaminated with traces of 19-norandrostenedione also results in testing positive for nandrolone.[2]
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]
19-Norandrosterone is also the basic skeleton structure for a family of C18 steroidal compounds called "dehydronorandrosterones".
References
- ↑ "THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD" (PDF). The World Anti-Doping Code. World Anti-Doping Agency. Archived (PDF) from the original on 10 April 2009. Retrieved 2009-05-14.
- ↑ 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.
- ↑ 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 Biomed. Sci. Appl. 723 (1–2): 157–72. doi:10.1016/S0378-4347(98)00541-6. PMID 10080643.
- ↑ 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. Retrieved 29 December 2008.
- ↑ 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. Retrieved 29 December 2008.
- ↑ 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.