- 19-Norandrostenedione
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19-Norandrostenedione Systematic (IUPAC) name (8R,9S,10R,13S,14S)-13-Methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-3,17-dione Clinical data Pregnancy cat. ? Legal status Schedule III (US) Routes Oral Identifiers CAS number 734-32-7 ATC code ? PubChem CID 92834 DrugBank DB01434 ChemSpider 83803 Chemical data Formula C18H24O2 Mol. mass 272.38 g/mol SMILES eMolecules & PubChem (what is this?) (verify) 19-Norandrostenedione (4-estrene-3,17-dione, NOR) is a precursor of the anabolic steroid nandrolone. Until 2005 19-Norandrostenedione was available without prescription in United States, where it was marketed as a prohormone, but it is now classified as a Schedule III drug. 19-Norandrostenedione is readily metabolized to nandrolone after oral administration, but its potency to transactivate the androgen receptor dependent reporter gene expression is 10 times lower as compared to dihydrotestosterone (DHT).[1]
In vivo experiments in castrated rats demonstrated that subcutaneous treatment with 19-norandrostenedione resulted only in a stimulation of the weight of the levator ani muscle, while the prostate and seminal vesicle weights remained completely unaffected. In contrast to its metabolite nandrolone, 19-norandrostenedione highly selectively stimulates the growth of the skeletal muscles but has only weak androgenic properties.[1]
In the early 2000s, contamination of androstenedione products with traces of 19-norandrostenedione caused false positives for doping tests for nandrolone because 19-norandrosterone is a metabolite of both nandrolone and 19-norandrostenedione. In a randomized controlled trial trace contamination of androstenedione with 19-norandrostenedione was sufficient for users of androstendione to test positive for nandrolone.[2] This detail became less relevant after androstenedione itself was banned by major sporting bodies.
See also
References
- ^ a b Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Schleipen B, Thevis M, Vollmer G, Zierau O (April 2008). "The prohormone 19-norandrostenedione displays selective androgen receptor modulator (SARM) like properties after subcutaneous administration". Toxicol. Lett. 177 (3): 198–204. doi:10.1016/j.toxlet.2008.01.014. PMID 18325697. http://linkinghub.elsevier.com/retrieve/pii/S0378-4274(08)00023-4.
- ^ 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.
Categories:- Steroids
- Anabolic steroids
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