19-Norandrosterone

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19-Norandrosterone
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-cyclopentaphenanthren-17-one
Identifiers
CAS number	1225-01-0
PubChem	9548753
SMILES	C12CC34CC(C4CC31CCC2=O)O
Properties
Molecular formula	C18H28O2
Molar mass	276.41 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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. Consumption of androstendione products contaminated with traces of 19-norandrostenedione also results in testing positive for nandrolone. 19-Norandrosterone has very little if any anabolic activity on its own, but may be used as a prohormone to the weak anabolic steroid 19-nordehydrotestosterone that has only about 70% of the potency of testosterone in humans.

Traces of 19-norandrosterone are 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 results 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. Consmption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.

19-Norandrosterone is also the basic skeleton structure for a family of C18 steroidal compounds called “dehydronorandrosterones”.

References

1. ^ “THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD”. The World Anti-Doping Code. World Anti-Doping Agency. http://www.wada-ama.org/rtecontent/document/2007_List_En.pdf. 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. http://jama.ama-assn.org/cgi/pmidlookup?view=long&pmid=11086369. 
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 Biomed. Sci. Appl. 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. http://meta.wkhealth.com/pt/pt-core/template-journal/lwwgateway/media/landingpage.htm?issn=0195-9131&volume=34&issue=9&spage=1436. 
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. http://linkinghub.elsevier.com/retrieve/pii/S0960-0760(01)00112-1. 
6. ^ Ayotte C (July 2006). “Significance of 19-norandrosterone in athletes’ urine samples”. Br J Sports Med 40 Suppl 1: i25–9. doi:10.1136/bjsm.2006.028027. 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. 

1.Debruyckere G, Van Peteghem C. Detection of 19-nortestosterone and its urinary metabolites in miniature pigs by gas chromatography-mass spectrometry. J Chromatogr. Apr 5;564(2):393-403, 1991

3.J Steroid Biochem. 1989 May;32(5):729-35.Links Aromatization of 19-norandrogens by porcine Leydig cells. Raeside JI, Renaud RL, Friendship RM. Department of Biomedical Sciences, University of Guelph, Ontario, Canada.

External links

• Testing for 19-norandrosterone
• Doping Control Procedures

Retrieved from “http://en.wikipedia.org/wiki/19-Norandrosterone”
Categories: Steroids

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