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Methasterone

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Methasterone
Clinical data
Other namesSuperdrol, methyldrostanolone, methasteron, drostanolone.
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • US: Schedule 3 controlled substance (US) as of August 29, 2012
Pharmacokinetic data
Bioavailability~50%
MetabolismHepatic
Elimination half-life8-12 hours
ExcretionRenal
Identifiers
  • 17β-Hydroxy-2α,17α-dimethyl-5α-androstane-3-one
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H34O2
Molar mass318.492 g/mol g·mol−1
3D model (JSmol)
  • O=C2C[C@@H]1CC[C@@H]3[C@@H]([C@@]1(C)C[C@H]2C)CC[C@]4([C@H]3CC[C@@]4(O)C)C
  • InChI=1S/C21H34O2/c1-13-12-19(2)14(11-18(13)22)5-6-15-16(19)7-9-20(3)17(15)8-10-21(20,4)23/h13-17,23H,5-12H2,1-4H3/t13-,14+,15-,16+,17+,19+,20+,21+/m1/s1 ☒N
  • Key:QCWCXSMWLJFBNM-FOVYBZIDSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Methasterone (nickname Superdrol), also known as methyldrostanolone, is an orally active anabolic-androgenic steroid (AAS) that was never marketed through legitimate channels for medicinal purposes. It was brought to market, instead, in a clandestine fashion as a “designer steroid.” Mebolazine is formed by hydrazone formation between 2 equivalents of methasterone with 1 equivalent of hydrazine.

History

The synthesis of methasterone is first mentioned in the literature in 1956 in connection with research conducted by Syntex Corporation in order to discover a compound with anti-tumor properties.[1] In a 1959 research journal article, it is initially mentioned and is elaborated upon where its method of synthesis is discussed in greater detail, its tumor inhibiting properties are verified, and it is noted as being a “potent orally active anabolic agent exhibiting only weak androgenic activity.”[2] The results of subsequent assays to determine methasterone’s anabolic and androgenic activity were published in Vida’s Androgens and Anabolic Agents, a dated but still standard reference, where it was noted that methasterone possessed the oral bioavailability of methyl-testosterone while being 400% as anabolic and 20% as androgenic, yielding a Q-ratio (also known as an anabolic to androgenic ratio) of 20, which is considered very high.[3]

Injectable counterpart

Methasterone was never a commercially available prescription drug. Its non-17α-alkylated counterpart, drostanolone, was commercialized by Syntex Corporation under the brand name Masteron.[4]

"Designer steroid"

Methasterone resurfaced in 2005 as a “designer steroid”.[5] It was brought to market by Designer Supplements as the primary ingredient of a dietary supplement named Superdrol. Its introduction into commerce may have represented an attempted circumvention of the U.S. Anabolic Steroids Control Act of 1990 (along with its 2004 revision), since the law is, in part, drug-specific;[6] methasterone, as is the case with many designer steroids, was not declared a Schedule III class anabolic steroid in that act because it was not commercially available at the time the act, and its subsequent revision, were signed into law.[7] Methasterone was therefore being sold as an over-the-counter dietary supplement.

Controversy and FDA involvement

It was in late 2005 that the status of methasterone, in addition to that of four other designer steroids, as an anabolic steroid was brought to public awareness by an article published in the Washington Post.[8] Don Catlin of the UCLA Olympic Laboratory, who conducted the studies, noted methasterone’s similarity to drostanolone. A warning by the FDA was issued soon after to the general public as well as to the distributor, Designer Supplements LLC, for the marketing of this compound.[9] Methasterone was subsequently added to the World Anti-Doping Agency (WADA) list of prohibited substances in sport.[10] Despite all of this, methasterone has resurfaced within the supplement industry on several occasions since its banning by WADA.[11]

Hepatoxicity

Methasterone is hepatotoxic (toxic to the liver). Many cases of liver damage due to the use of methasterone have been cited in the medical literature.[12][13][14][15]

References

  1. ^ H. J. Ringold; G. Rosenkranz (1956). "Steroids. LXXXIII. Synthesis of 2-Methyl and 2,2-Dimethyl Hormone Analogs". Journal of Organic Chemistry. 21: 1333–1335. doi:10.1021/jo01117a625. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  2. ^ Ringold, H. J., E. Batres, O. Halpern, and E. Necoechea (1959). "Steroids. CV.1 2-Methyl and 2-Hydroxymethylene-androstane Derivatives". Journal of the American Chemical Society. 81 (2): 427–432. doi:10.1021/ja01511a040.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ Julius A. Vida (1969). Androgens and Anabolic Agents: Chemistry and Pharmacology. New York: Academic Press. pp. 23 & 168.
  4. ^ "Superdrol, masteron en oxy komen uit hetzelfde nest" [Superdrol, Masteron, and Oxy come from the same nest]". Ergogenics.org. Retrieved February 2009. {{cite web}}: Check date values in: |accessdate= (help)
  5. ^ Van Enoo, Peter; Frans T. Delbeke (2006). "Metabolism and excretion of anabolic steroids in doping control—New steroids and new insights". Journal of Steroid Biochemistry & Molecular Biology. 101: 173. doi:10.1016/j.jsbmb.2006.06.024. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  6. ^ "Implementation of the Anabolic Steroid Control Act of 2004". Office of Divesion Control, Drug Enforcement Administration, Department of Justice. Retrieved February 2009. {{cite web}}: Check date values in: |accessdate= (help)
  7. ^ Shipley, Amy, Bonnie Berkowitz and Christina Rivero (October 18, 2005). "Designer Steroids Hide and Seek". The Washington Post. Retrieved February 2009. {{cite news}}: Check date values in: |accessdate= (help)CS1 maint: multiple names: authors list (link)
  8. ^ Amy Shipley (November 30, 2005). "Steroids Detected in Dietary Tablets". The Washington Post. Retrieved February 2009. {{cite news}}: Check date values in: |accessdate= (help)
  9. ^ "FDA Warns Manufacturers About Illegal Steroid Products Sold as Dietary Supplements". U.S. Food and Drug Administration. March 9, 2006. Retrieved February 2009. {{cite web}}: Check date values in: |accessdate= (help)
  10. ^ "The World Anti-Doping Code: The 2009 Prohibited List: International Standard" (PDF). World Anti-Doping Agency. Retrieved February 2009. {{cite web}}: Check date values in: |accessdate= (help)
  11. ^ David Epstein; George Dohrmann (May 18, 2009). "What You Don't Know Might Kill You: Would-be experts and untested products feed a $20 billion obsession with better performance across all levels of sports". Sports Illustrated.
  12. ^ Jasiurkowski, Beata, Jaya Raj, David Wisinger, Richard Carlson, Lixian Zou, and Abdul Nadir (2006). "Cholestatic Jaundice and IgA Nephropathy Induced by OTC Muscle Building Agent Superdrol". American Journal of Gastroenterology. 101 (11): 2659–2662. doi:10.1111/j.1572-0241.2006.00735.x.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  13. ^ Nasr, John; Jawad Ahmad (2008). "Severe Cholestasis and Renal Failure Associated with the Use of the Designer Steroid Superdrol (Methasteron): A Case Report and Literature Review". Digestive Diseases and Sciences. 10: 1007. {{cite journal}}: Unknown parameter |lastauthoramp= ignored (|name-list-style= suggested) (help)
  14. ^ L. Shah, Neeral, Isabel Zacharias, Urmila Khettry, Nezam Afdhal, and Fredric D. Gordon (2008). "Methasteron-Associated Cholestatic Liver Injury: Clinicopathologic Findings in 5 Cases". Clinical Gastroenterology and Hepatology. 6 (2): 255–258. doi:10.1016/j.cgh.2007.11.010.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ Singh V, Rudraraju M, Carey EJ, Byrne TJ, Vargas HE, Williams JE, Balan V, Douglas DD, Rakela J (March 2009). "Severe Hepatotoxicity Caused by a Methasteron-containing, Performance-enhancing Supplement". Journal of Clinical Gastroenterology. 43 (3). doi:10.1097/mcg.0b013e31815a5796.
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