Bolasterone

Bolasterone
Clinical data
Trade namesMyagen, Methosarb
Other namesU-19763; NSC-66233; 7α,17α-Dimethyltestosterone; 7α,17α-Dimethylandrost-4-en-17β-ol-3-one, Piratestosterone.
Routes of
administration		By mouth
Legal status
Legal status
Identifiers
  • (7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,10,13,17-tetramethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.015.018 Edit this at Wikidata
Chemical and physical data
FormulaC21H32O2
Molar mass316.485 g·mol−1
3D model (JSmol)
  • O=C4\C=C3/[C@]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2[C@H](C)C3)C)(C)CC4
  • InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16+,17+,18-,19+,20+,21+/m1/s1
  • Key:IVFYLRMMHVYGJH-VLOLGRDOSA-N

Bolasterone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name) (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. It has close structural similarity to testosterone, and like methyltestosterone has a methyl group at C17α in order to increase oral bioavailability. In addition, it is also 7α-methylated, similar to its 7β-methylated isomer calusterone. The medication has a low to moderate ratio of anabolic to androgenic activity, similar to that of fluoxymesterone.

Bolasterone is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports. The medication was initially developed by Upjohn for veterinary use and was stolen by the East German Stasi for use in athletes by the Forschungsinstitut für Körperkultur und Sport (FKS) in the German Democratic Republic.[citation needed]

Chemistry

Synthesis

The chemical synthesis was reported: Patent:

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

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. 1 2 3 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 646–. ISBN 978-1-4757-2085-3.
  3. ↑ Morton IK, Hall JS (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 52–. ISBN 978-94-011-4439-1.
  4. ↑ Kochakian CD (6 December 2012). Anabolic-Androgenic Steroids. Springer Science & Business Media. pp. 377, 401. ISBN 978-3-642-66353-6.
  5. ↑ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.
  6. ↑ Campbell, J. A.; Babcock, J. C. (August 1959). "The Synthesis of Some 7α- and 7β-Methyl Steroid Hormones 1". Journal of the American Chemical Society. 81 (15): 4069–4074. doi:10.1021/ja01524a063. Retrieved 29 January 2026.
  7. ↑ U.S. patent 3,341,557 Babcock, J. C.; Campbell, J. A.; Upjohn Co (1967).