Structure via PubChem · Public domain (PubChem)
5alpha-19-norandrosterone
Sign in to saveAlso known as 19-Noretiocholanolone, 19-Noreoiandrosterone, 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). Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.
Chemical data
- Formula
- C18H28O2
- Molecular weight
- 276.4 g/mol
- 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
- SMILES
- C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O
- InChIKey
- UOUIARGWRPHDBX-CQZDKXCPSA-N
- XLogP
- 3.3
- Polar surface area
- 37.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- steroid
- Mass
- 276.20893
Show 4 more facts
- chemical formula
- C₁₈H₂₈O₂
- canonical SMILES
- CC12CCC3C4CCC(CC4CCC3C1CCC2=O)O
- isomeric SMILES
- C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O
- Commons category
- 19-Norandrosterone
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- See also
- References
- External links
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). Consumption of androstendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.
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, 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 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. Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.
Excerpted from Wikipedia’s “5alpha-19-norandrosterone” article, available under the CC BY-SA 4.0 licence.