19-Norandrosterone
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Names | |
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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
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Identifiers | |
1225-01-0 ![]() |
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ChEBI | CHEBI:36412 ![]() |
ChemSpider | 7827676 ![]() |
Jmol 3D model | Interactive image Interactive image |
PubChem | 9548753 |
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Properties | |
C18H28O2 | |
Molar mass | 276.41 g/mol |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
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