19-Norandrosterone

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-cyclopenta[a]phenanthren-17-one
Identifiers
CAS number	1225-01-0 N
PubChem	9548753
ChemSpider	7827676 Y
ChEBI	CHEBI:36412 Y
Jmol-3D images	Image 1 Image 2
SMILES C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O O=C2[C@]1(CC[C@H]3[C@H]([C@@H]1CC2)CC[C@H]4C[C@H](O)CC[C@H]34)C
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 InChI=1/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 Key: UOUIARGWRPHDBX-CQZDKXCPBD
Properties
Molecular formula	C18H28O2
Molar mass	276.41 g/mol
N (verify) (what is: Y/N?) 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.^[1] Consumption of androstendione products contaminated with traces of 19-norandrostenedione also results in testing positive for nandrolone.^[2] 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,^[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 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.^[6] Consmption 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

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 (Suppl 1): i25–9. doi:10.1136/bjsm.2006.028027. PMC 2657496. PMID 16799098. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2657496. 
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