Chemistry:Bolasterone
Bolasterone (INN, USAN) (brand names Myagen, Methosarb; former developmental code name U-19763), also known as 7α,17α-dimethyltestosterone, is a 17α-alkylated androgen/anabolic steroid (AAS) which is used in veterinary medicine.[1][2] It has close structural similarity to testosterone, and like methyltestosterone has a methyl group at C17α in order to increase oral bioavailability.[1] In addition, it is also 7α-methylated, similar to its 7β-methylated isomer calusterone.[1] The medication has a low to moderate ratio of anabolic to androgenic activity, similar to that of fluoxymesterone.[3]
Bolasterone is on the World Anti-Doping Agency's list of prohibited substances,[4] and is therefore banned from use in most major sports.
Chemistry
Synthesis
The chemical synthesis was reported:[5] Patent:[6]
The oxidation of methyltestosterone [58-18-4] (1) with chloranil gives 17alpha-methyl-6,7-dehydrotestosterone [5585-85-3] (2). The conjugate addition of methylmagnesium bromide in the presence of a catalytic amount of cuprous iodide (c.f. Gilman reagent) gives a mixture of bolasterone and calusterone, with the former predominating.
See also
- Mibolerone (19-normethyl-bolasterone)
References
- ↑ 1.0 1.1 1.2 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 646–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA646.
- ↑ 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.
- ↑ Anabolic-Androgenic Steroids. Springer Science & Business Media. 6 December 2012. pp. 377, 401. ISBN 978-3-642-66353-6. https://books.google.com/books?id=3-LrCAAAQBAJ&pg=PA377.
- ↑ "The World Anti-Doping Code: The 2020 Prohibited List". World Anti-Doping Agency. https://www.wada-ama.org/sites/default/files/wada_2020_english_prohibited_list_0.pdf.
- ↑ "The Synthesis of Some 7α- and 7β-Methyl Steroid Hormones 1". Journal of the American Chemical Society 81 (15): 4069–4074. August 1959. doi:10.1021/ja01524a063. https://pubs.acs.org/doi/abs/10.1021/ja01524a063. Retrieved 29 January 2026.
- ↑ U.S. Patent 3,341,557 Babcock, J. C.; Campbell, J. A.; Upjohn Co (1967).
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