Boldenone: Difference between revisions
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Undid last revision. See boldenone undecylenate. I did not insert a deliberate factual error, I corrected what appears to be one. Tag: review edit |
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'''Boldenone''', also known as '''Δ<sup>1</sup>-testosterone''', is a [[ |
'''Boldenone''', also known as '''Δ<sup>1</sup>-testosterone''', is a [[natural product|naturally occurring]] [[anabolic–androgenic steroid]] (AAS) and the 1(2)-[[dehydrogenated]] [[structural analog|analogue]] of [[testosterone]].<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=131–}}</ref><ref name="MortonHall2012">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}}</ref><ref name="Drugs.com">{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|accessdate=28 April 2017}}</ref><ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=483–}}</ref> Boldenone itself has never been marketed; as a [[pharmaceutical drug]], it is used as [[boldenone undecylenate]], the [[undecylic acid|undecylenate]] [[ester]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> |
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{{See also|List of androgens/anabolic steroids}} |
{{See also|List of androgens/anabolic steroids}} |
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Boldenone, also known as '''Δ<sup>1</sup>-testosterone''', '''1-dehydrotestosterone''', or '''androsta-1,4-dien-17β-ol-3-one''', is a [[ |
Boldenone, also known as '''Δ<sup>1</sup>-testosterone''', '''1-dehydrotestosterone''', or '''androsta-1,4-dien-17β-ol-3-one''', is a [[natural product|naturally occurring]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is specifically testosterone with a [[double bond]] between the C1 and C2 positions.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> A related compound is [[quinbolone]], the 17-[[cyclopentene|cyclopentenyl]] [[enol]] [[ether]] of boldenone.<ref name="Elks2014" /><ref name="IndexNominum2000" /> |
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==History== |
==History== |
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Revision as of 06:51, 11 November 2017
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| Clinical data | |
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| AHFS/Drugs.com | International Drug Names |
| Pregnancy category | |
| Routes of administration | Intramuscular injection |
| ATC code |
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| Legal status | |
| Legal status |
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| Pharmacokinetic data | |
| Elimination half-life | Intramuscular: 14 days (as boldenone undecylenate)[citation needed] |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.011.533 |
| Chemical and physical data | |
| Formula | C19H26O2 |
| Molar mass | 286.409 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 165 °C (329 °F) |
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  (what is this?) (verify) | |
Boldenone, also known as Δ1-testosterone, is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone.[1][2][3][4][5] Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.[1][2][5]
Side effects
Pharmacology
Pharmacodynamics
Like other AAS, boldenone is an agonist of the androgen receptor (AR).[5] The activity of boldenone is mainly anabolic, with a low androgenic potency. Boldenone will increase nitrogen retention, protein synthesis, increases appetite and stimulates the release of erythropoietin in the kidneys.[6] Boldenone was synthesized in an attempt to create a long-acting injectable metandienone, for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects.[medical citation needed] Although commonly compared to nandrolone, boldenone lacks progesterone receptor interaction and associated progestogenic side effects.
Chemistry
Boldenone, also known as Δ1-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a naturally occurring androstane steroid and a derivative of testosterone.[1][2][5] It is specifically testosterone with a double bond between the C1 and C2 positions.[1][2][5] A related compound is quinbolone, the 17-cyclopentenyl enol ether of boldenone.[1][2]
History
Ciba reportedly patented boldenone in 1949.[5] It subsequently developed several experimental esters of the drug in the 1950s and 1960s.[5] One of these was boldenone undecylenate, which was introduced for clinical use under the brand name Parenabol and saw some use in the late 1960s and early 1970s.[5] However, it was discontinued before the end of the 1970s.[5] Subsequently, boldenone undecylenate was introduced by Squibb under the brand name Equipose for veterinary use most commonly in horses.[5]
Society and culture
Generic names
Boldenone is the generic name of the drug and its INN and BAN.[1][2][3][4]
Brand names
Boldenone is marketed as veterinary drug as boldenone undecylenate (a derivative of boldenone) under the following brand names: Boldebal H, Equipoise, and Sybolin.[4] It is marketed as a veterinary combination drug with methandriol under the brand name Drive.[4]
Use in sports
Baseball
Boldenone is among the substances banned by Major League Baseball, as well as most other major athletic organizations. Los Angeles Angels minor league outfielder Reynaldo Ruiz in September 2010[7] and Philadelphia Phillies minor league pitcher San Lazaro Solano in January 2011[8] each received a 50-game suspension for the 2011 season as a result of testing positive for a metabolite of boldenone. Jenrry Mejia, formerly of the New York Mets, was suspended in July 2015 when he tested positive for boldenone and stanozolol, and in February 2016 he again tested positive for boldenone; this marked Mejia's third positive test for a performance-enhancing drug, for which he received the first PED-related lifetime ban in MLB history.[9] Abraham Almonte was suspended for 80 games before the 2016 season after testing positive for boldenone.[10]
Mixed martial arts
Stephan Bonnar and Josh Barnett, mixed martial arts (MMA) fighters from the UFC and PRIDE Fighting Championships, have also tested positive for the banned substance.[11] After the World Extreme Cagefighting show on January 20, 2006 Muay Thai turned MMA fighter Kit Cope also tested positive for boldenone.[12] Following the Strikeforce card on June 22, 2007 former PRIDE and UFC fighter Phil Baroni tested positive for boldenone, as well as stanozolol.[13] At a K-1 WGP event in Las Vegas on August 17, 2007 two fighters, Rickard Nordstrand and Zabit Samedov, both tested positive for boldenone.[14] Alexandre Franca Nogueira tested positive for boldenone in July 2008.[15]
Antonio Silva tested positive for boldenone after his July 26, 2008 fight against Justin Eilers in the EliteXC promotion. Silva was suspended by the California State Athletic Commission for a year and fined $2500.[16]
Australian Football League
Justin Charles, a former minor league baseball player with the Florida Marlins, of Richmond FC tested positive for the substance in 1997 and was suspended for 16 matches.[17]
Major League Soccer
Jon Conway (goal keeper) and Jeff Parke (defender) of the New York Red Bulls both tested positive for the substance in 2008 and were suspended 10 games and fined 10% of their annual income. They are also the first to violate MLS drug policy.[18]
Horse racing
Leading horse trainer Gai Waterhouse was fined $10,000 after being found guilty on May 15, 2008 of presenting a horse to the races with a prohibited substance in its system. Her horse Perfectly Poised was found to have traces of the banned substance boldenone in its system after finishing second at Canterbury in April 2007.[19]
References
- ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3.
- ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 131–. ISBN 978-3-88763-075-1.
- ^ a b I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 52–. ISBN 978-94-011-4439-1.
- ^ a b c d "Boldenone international brand names". Drugs.com. Retrieved 28 April 2017.
- ^ a b c d e f g h i j William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 483–. ISBN 978-0-9828280-1-4.
- ^ Forbes GB (1985) The effect of anabolic steroids on lean body mass the dose response curve. Metab Clin Exp 34(6) 571–573
- ^ "Three Minor League players suspended". MLB.com. September 30, 2010.
- ^ "Phillies Minor League Pitcher San Lazaro Solano Suspended". MLB.com. January 20, 2011.
- ^ "Jenrry Mejia first player to get permanent ban for 3rd positive PED test". ESPN.com. February 13, 2016.
- ^ "Indians' Almonte suspended 80 games for failed drug test". Yahoo.com. February 26, 2016.
- ^ Ivan Trembow (2006-11-06). "Bonnar Suspended 9 Months for Steroid Use". MMAWeekly.com. Archived from the original on 2009-08-03. Retrieved 2007-07-03.
{{cite web}}: Unknown parameter|deadurl=ignored (|url-status=suggested) (help) - ^ Josh Gross (2007-01-20). "Update: Cope Tests Positive for Steroids". Sherdog.com. Retrieved 2007-07-03.
- ^ Ken Pishna (2007-07-03). "Breaking News: Phil Baroni Tests Positive". MMAWeekly.com. Retrieved 2007-07-03.
- ^ Brent Brookhouse (2007-08-17). "Two More Positive Drug Tests In Fight World". bloodyelbow.com. Archived from the original on September 30, 2007. Retrieved 2007-08-17.
- ^ "Alexandre Nogueira tests positive for boldenone". Sherdog. 2008-07-08. Retrieved 2017-02-03.
- ^ "Silva, Dewees test positive". Sherdog. 2008-08-21. Retrieved 2017-02-03.
- ^ Robinson, Mark (2011-06-26). "Charles kept playing after positive test". Retrieved 2017-02-03.
- ^ "Conway, Parke banned 10 matches for positive drug tests". ESPNFC.com.
- ^ Pandaram, Jamie (2008-05-16). "Fined $10,000, but Waterhouse claims she's been vindicated - Horseracing - Sport". www.smh.com.au. Retrieved 2017-02-03.