Chemistry:Boldenone

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Boldenone (developmental code name RU-18761), 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]

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]

Sources

Boldenone occurs naturally in the scent gland of Ilybius fenestratus, a species of aquatic beetle.[1]

In calves not fed boldenone, their urine 17α-boldenone content is strictly related to the phytosterol content of the diet. These naturally occurring amounts present are below doping attention limits.[7]

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]

In Ukraine, it is marketed for human consumption as the injectable steroid Boldenol.[8]

Doping in sports

There are many known cases of doping in sports with boldenone undecylenate by professional athletes.

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 640–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640. 
  2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 131–. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131. 
  3. ↑ 3.0 3.1 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 52–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52. 
  4. ↑ 4.0 4.1 4.2 4.3 "Boldenone international brand names". Drugs.com. https://www.drugs.com/international/boldenone.html. 
  5. ↑ 5.00 5.01 5.02 5.03 5.04 5.05 5.06 5.07 5.08 5.09 Anabolics. Molecular Nutrition Llc. 2011. pp. 483–490. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483. 
  6. ↑ "The effect of anabolic steroids on lean body mass: the dose response curve". Metabolism: Clinical and Experimental 34 (6): 571–3. June 1985. doi:10.1016/0026-0495(85)90196-9. PMID 3999979. 
  7. ↑ "Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites". Journal of Agricultural and Food Chemistry 55 (20): 8275–83. October 2007. doi:10.1021/jf071097c. PMID 17844992. 
  8. ↑ "Boldenol 200 (boldenone undecylenate)". Lyka Labs. http://ukroids.club/index.php?main_page=product_info&products_id=5071. 

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