Nandrolone

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Nandrolone
Nandrolone.svg
Systematic (IUPAC) name
17β-Hydroxyestra-4-en-3-one
Clinical data
Pronunciation /ˈnændrəln/[1]
Pregnancy
category
Routes of
administration
Intramuscular
Legal status
Legal status
Pharmacokinetic data
Bioavailability 2.24% (Oral)
100% (Intramuscular)
Metabolism Hepatic
Biological half-life 6 days
Excretion ~21 days
Identifiers
CAS Number 434-22-0 YesY
ATC code A14AB01 (WHO) S01XA11 (WHO)
PubChem CID 9904
IUPHAR/BPS 6949
DrugBank DB00984 N
ChemSpider 9520 YesY
UNII 6PG9VR430D YesY
ChEBI CHEBI:7466 YesY
ChEMBL CHEMBL757 YesY
Synonyms Nortestosterone, 19-nortestosterone, nor-19-testosterone, norandrostenolone, nortestosterone, nortestrionate, nortestonate, oestrenolone, estrenolone, SG-4341[2][3]
Chemical data
Formula C18H26O2
Molar mass 274.40
 NYesY (what is this?)  (verify)

Nandrolone (INN, BAN), also known as 19-nortestosterone, is an anabolic-androgenic steroid (AAS).[2][3] Nandrolone is most commonly sold commercially as its decanoate ester, nandrolone decanoate (Deca-Durabolin, Eubolin, Retabolil), less commonly as a phenylpropionate ester, nandrolone phenylpropionate (Durabolin, Fenobolin), and also as a variety of other esters (see nandrolone ester). Nandrolone decanoate is used in the treatment of osteoporosis in postmenopausal women (though now not recommended) at a dose of 50 mg every three weeks. It is also used for some aplastic anemias.

Metabolism[edit]

The positive effects of the drug include muscle growth, appetite stimulation and increased red blood cell production and bone density.[medical citation needed] Clinical studies have shown it to be effective in treating anaemia, osteoporosis and some forms of neoplasia including breast cancer, and also acts as a progestin-based contraceptive. For these reasons,[citation needed] in the United States nandrolone received FDA approval in 1983.

Because nandrolone is not broken down into DHT, the deleterious effects common to most anabolic steroids on the scalp, skin, and prostate are lessened to a degree;[medical citation needed] but is rather broken down to the much weaker androgen dihydronandrolone. The lack of alkylation on the 17α-carbon drastically reduces the drug's liver toxicity.[medical citation needed] Estrogenic effects resulting from reaction with aromatase are also reduced due to lessened enzyme interaction,[4] but effects such as gynaecomastia and reduced libido still occur in larger doses because of other mechanisms. Other side-effects of abuse can include erectile dysfunction and cardiovascular damage, as well as several ailments resulting from the drug's effect of lowering levels of luteinizing hormone through negative feedback. Erectile dysfunction is attributed to the weaker action of dihydronandrolone in the penis since dihydrotestosterone is a known sexual modulator.

Detection method[edit]

Nandrolone use is directly detectable in hair or indirectly detectable in urine by testing for the presence of 19-norandrosterone, a metabolite. The International Olympic Committee has set a limit of 2.0 μg/L of 19-norandrosterone in urine as the upper limit,[5] beyond which an athlete is suspected of doping. In the largest nandrolone study performed on 621 athletes at the 1998 Nagano Olympic Games, no athlete tested over 0.4 μg/L. 19-Norandrosterone was identified as a trace contaminant in commercial preparations of androstenedione, which until 2004 was available without a prescription as a dietary supplement in the U.S.[6][7][8][9]

A number of nandrolone cases in athletics occurred in 1999, which included high profile athletes such as Merlene Ottey, Dieter Baumann and Linford Christie.[10] However, the following year the detection method for nandrolone at the time was proved to be faulty. Mark Richardson, a British Olympic relay runner who tested positive for the substance, gave a significant amount of urine samples in a controlled environment and delivered a positive test for the drug, demonstrating that false positives could occur, which led to an overhaul of his competitive ban.[11]

Heavy consumption of the essential amino acid lysine (as indicated in the treatment of cold sores) has allegedly shown false positives in some and was cited by American shotputter C. J. Hunter as the reason for his positive test, though in 2004 he admitted to a federal grand jury that he had injected nandrolone.[12] A possible cause of incorrect urine test results is the presence of metabolites from other anabolic steroids, though modern urinalysis can usually determine the exact steroid used by analyzing the ratio of the two remaining nandrolone metabolites. As a result of the numerous overturned verdicts, the testing procedure was reviewed by UK Sport. On October 5, 2007, five-time gold medalist for track and field Marion Jones admitted to use of the drug, and was sentenced to six months in jail for lying to a federal grand jury in 2000.[13]

QV Nandrolone Deca, a form of nandrolone used by athletes.

Mass spectrometry is also used to detect small samples of nandrolone in urine samples, as it has a unique molar mass.

Publicized cases[edit]

Synthesis[edit]

The elaboration of a method for the reduction of aromatic rings to the corresponding dihydrobenzenes under controlled conditions by A. J. Birch opened a convenient route to compounds related to the putative norprogesterone.

19-Nortestosterone synthesis:[29] alternative:[30][31]

This reaction, now known as the Birch reduction,[32] is typified by the treatment of the monomethyl ether of estradiol (1) with a solution of lithium metal in liquid ammonia in the presence of alcohol as a proton source. Initial reaction constituents of 1,4-dimetalation of the most electron deficient positions of the aromatic ring–in the case of an estrogen, the 1 and 4-positions. Rxn of the intermediate with the proton source leads to a dihydrobenzene; a special virtue of this sequence in steroids is the fact that the double bind at 2 is in effect becomes an enol ether moiety. Treatment of this product (2) with weak acid, oxalic acid for e.g., leads to the hydrolysis of the enol ether, producing β,γ-unconjugated ketone 3. Hydrolysis under more sternuous conditions (mineral acids) results in migration/conjugation of the olefin to yield nandrolone (4).

Esters[edit]

See also[edit]

References[edit]

  1. ^ http://dictionary.cambridge.org/dictionary/british/nandrolone
  2. ^ a b J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 660–. ISBN 978-1-4757-2085-3. 
  3. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 716–. ISBN 978-3-88763-075-1. 
  4. ^ Brueggemeier RW (September 16, 2006). "Sex Hormones (Male): Analogs and Antagonists". In Meyers RA. Encyclopedia of Molecular Cell Biology and Molecular Medicine. Encyclopedia of Molecular Cell Biology and Molecular Medicine (abstract). John Wiley & Sons. doi:10.1002/3527600906.mcb.200500066. ISBN 3527600906. Retrieved March 2, 2013. 
  5. ^ "Clarification about Nandrolone Testing". World Anti-Doping Agency. 2005-05-30. Retrieved 2012-01-31. 
  6. ^ Bresson M, Cirimele V, Villain M, Kintz P (May 2006). "Doping control for metandienone using hair analyzed by gas chromatography-tandem mass spectrometry". J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 836 (1–2): 124–8. doi:10.1016/j.jchromb.2006.03.040. PMID 16597518. 
  7. ^ Ueki M, Ikekita A, Takao Y (2000). "[Nandrolone metabolite in urine of Nagano Olympic athlete]". Jap. J. For. Tox. (in Japanese) 18: 198–199. 
  8. ^ 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. 
  9. ^ Baselt RC (2008). Disposition of Toxic Drugs and Chemicals in Man (8th ed.). Foster City, CA: Biomedical Publications. pp. 1078–1080. ISBN 0-9626523-7-7. 
  10. ^ Baron, Peter (2000-09-19). The Drugs Issue: Baumann to fight all the way. The Daily Telegraph. Retrieved on 2010-11-13.
  11. ^ Richardson M (2004-02-19). "Athletics: Mark Richardson explains how he felt at his disciplinary hearing". Athletics (London: The Guardian). Retrieved 2010-11-13. It was as daunting a line-up as I had ever faced on athletics tracks 
  12. ^ "Track Star Marion Jones to Admit Steroid Use". National Public Radio. 2007-10-05. Retrieved 2009-11-09. 
  13. ^ UK Sport Anti-doping Directorate (January 2000). Nandrolone Review (PDF) (Report). UK Sport. Archived from the original (PDF) on 2005-04-02. Retrieved 2013-02-02. 
  14. ^ "Disgraced Hudson faces sack from Bulls". Daily Mail (London). March 10, 2005. 
  15. ^ "Guardiola fails second test". BBC News. November 28, 2001. 
  16. ^ "Korda failed Wimbledon drugs test". BBC. December 23, 1998. 
  17. ^ All-Star Roster Shows Up on Mitchell Report washingtonpost.com, 12-13-2007
  18. ^ "BBC Sport". 
  19. ^ "Royce Gracie Suspended, Fined For Steroids | TheSweetScience.com Boxing". Thesweetscience.com. Retrieved November 9, 2009. 
  20. ^ "Cricinfo - A tale of intrigue, injuries and incidents". Content-ind.cricinfo.com. January 1, 1970. Retrieved November 9, 2009. 
  21. ^ "Sean Sherk". Cage Potato. January 1, 1970. Retrieved September 12, 2010. 
  22. ^ "news.bbc.co.uk/2/hi/sport/411951.stm". BBC News. August 4, 1999. Retrieved November 9, 2009. 
  23. ^ "Former NBA player banned after steroid test". USA Today. February 13, 2010. 
  24. ^ "Three Minor League players suspended". MLB.com. September 30, 2010. 
  25. ^ Indian athlete Rani Yadav fails dope test at Commonwealth Games, The Times of India, October 13, 2010.
  26. ^ "news.bbc.co.uk/sport1/hi/tennis/3381111.stm". BBC News. January 9, 2004. Retrieved July 2, 2011. 
  27. ^ "http://news.bbc.co.uk/sport1/hi/tennis/3547917.stm". BBC News. March 10, 2004. Retrieved July 2, 2011.  External link in |title= (help)
  28. ^ "Minor leaguer suspended". August 13, 2014. 
  29. ^ Wilds, A. L.; Nelson, Norman A. (1953). "The Facile Synthesis of 19-Nortestosterone and 19-Norandrostenedione from Estrone". Journal of the American Chemical Society 75 (21): 5366. doi:10.1021/ja01117a065. 
  30. ^ Ueberwasser, H.; Heusler, K.; Kalvoda, J.; Meystre, Ch.; Wieland, P.; Anner, G.; Wettstein, A. (1963). "19-Norsteroide II. Ein einfaches Herstellungsverfahren für 19-Norandrostan-Derivate. Über Steroide, 193. Mitteilung". Helvetica Chimica Acta 46: 344. doi:10.1002/hlca.19630460135. 
  31. ^ Shimizu, Isao; Naito, Yoichiro; Tsuji, Jiro (1980). "Synthesis of optically active (+)-19-nortestosterone by asymmetric bis-annulation reaction". Tetrahedron Letters 21 (5): 487. doi:10.1016/S0040-4039(00)71440-7. 
  32. ^ Birch, Arthur J. (1950). "The reduction of organic compounds by metal-ammonia solutions". Quarterly Reviews, Chemical Society 4: 69. doi:10.1039/QR9500400069. 
  33. ^ DeWytt, E. D.; Overbeek, O.; Overbeek, G. A.; U.S. Patent 2,998,423 (1961 to Organon).
  34. ^ CH 206119  (1939 to Gesellschaft für Chemische Industrie Basel).