Methasterone

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Methasterone
Clinical data
Other namesSuperdrol; Methyldrostanolone; Methasteron; 2α,17α-Dimethyl-4,5α-dihydrotestosterone; 2α,17α-Dimethyl-DHT; 2α,17α-Dimethyl-5α-androstan-17β-ol-3-one
Routes of
administration		oral
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Bioavailability~50%[citation needed]
MetabolismLiver
Elimination half-life8–12 hours
ExcretionUrine
Identifiers
  • (2R,5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2,10,13,17-tetramethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC21H34O2
Molar mass318.501 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, also known as methyldrostanolone and known by the nickname Superdrol, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was sold legally for 9 years as a body building supplement. Because of this lengthy time being legal it has more studies and references than most other designer steroids.

Medical uses

Methasterone was never a commercially available prescription drug. Its non-17α-alkylated counterpart, drostanolone propionate, was commercialized by Syntex Corporation under the brand name Masteron.[1]

Non-medical uses

Methasterone resurfaced in 2005 as a "designer steroid".[2] 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;[3] 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.[4] Methasterone was therefore being sold as an over-the-counter dietary supplement.

Side effects

See also: Anabolic steroid § Adverse effects

Methasterone is hepatotoxic (toxic to the liver). Several cases of liver damage due to the use of methasterone have been cited in the medical literature.[5][6][7][8]

Chemistry

See also: List of androgens/anabolic steroids

Methasterone, also known as 2α,17α-dimethyl-5α-dihydrotestosterone (2α,17α-dimethyl-DHT) or as 2α,17α-dimethyl-5α-androstan-17β-ol-3-one, is a synthetic androstane steroid and a 17α-alkylated derivative of DHT.

Mebolazine is formed by hydrazone formation between two equivalents of methasterone with one 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.[9] 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."[10] 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 methyltestosterone while being 400% as anabolic and 20% as androgenic, yielding a Q-ratio (anabolic to androgenic ratio) of 20, which is considered very high.[11]

Designer steroid

It was in late 2005 that the reclassification of methasterone as AAS (as well as that of four other designer steroids) was brought to public awareness via an article published in the Washington Post.[12] 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.[13] Methasterone was subsequently added to the World Anti-Doping Agency (WADA) list of prohibited substances in sport.[14] Despite all of this, methasterone has resurfaced within the supplement industry on several occasions since its banning by WADA.[15]

References

  1. ^ "Superdrol, masteron en oxy komen uit hetzelfde nest" [Superdrol, Masteron, and Oxy come from the same nest]". Ergogenics.org. Retrieved 21 February 2009.
  2. ^ Van Eenoo P, Delbeke FT (November 2006). "Metabolism and excretion of anabolic steroids in doping control--new steroids and new insights". The Journal of Steroid Biochemistry and Molecular Biology. 101 (4–5): 161–178. doi:10.1016/j.jsbmb.2006.06.024. PMID 17000101. S2CID 33621513.
  3. ^ "Implementation of the Anabolic Steroid Control Act of 2004". Office of Division Control, Drug Enforcement Administration, Department of Justice. Archived from the original on 16 February 2012. Retrieved 21 February 2009.
  4. ^ Shipley A, Berkowitz B, Rivero C (October 18, 2005). "Designer Steroids Hide and Seek". The Washington Post. Retrieved 21 February 2009.
  5. ^ Jasiurkowski B, Raj J, Wisinger D, Carlson R, Zou L, Nadir A (November 2006). "Cholestatic jaundice and IgA nephropathy induced by OTC muscle building agent superdrol". The American Journal of Gastroenterology. 101 (11): 2659–2662. doi:10.1111/j.1572-0241.2006.00735.x. PMID 16952289. S2CID 5889075.
  6. ^ Nasr J, Ahmad J (May 2009). "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. 54 (5): 1144–1146. doi:10.1007/s10620-008-0457-x. PMID 18720005. S2CID 21819008.
  7. ^ Shah NL, Zacharias I, Khettry U, Afdhal N, Gordon FD (February 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. PMID 18187367.
  8. ^ Singh V, Rudraraju M, Carey EJ, Byrne TJ, Vargas HE, Williams JE, et al. (March 2009). "Severe hepatotoxicity caused by a methasteron-containing performance-enhancing supplement". Journal of Clinical Gastroenterology. 43 (3): 287. doi:10.1097/mcg.0b013e31815a5796. PMID 18813027.
  9. ^ Ringold H, Rosenkranz G (November 1956). "Steroids. LXXXIII. Synthesis of 2-Methyl and 2,2-Dimethyl Hormone Analogs". Journal of Organic Chemistry. 21: 1333–1335. doi:10.1021/jo01117a625.
  10. ^ Ringold HJ, Batres E, Halpern O, Necoechea E (January 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.
  11. ^ Vida JA (1969). Androgens and Anabolic Agents: Chemistry and Pharmacology. New York: Academic Press. pp. 23 & 168.
  12. ^ Shipley A (November 30, 2005). "Steroids Detected in Dietary Tablets". The Washington Post. Retrieved 21 February 2009.
  13. ^ "FDA Warns Manufacturers About Illegal Steroid Products Sold as Dietary Supplements". U.S. Food and Drug Administration. March 9, 2006. Retrieved 21 February 2009.
  14. ^ "The World Anti-Doping Code: The 2009 Prohibited List: International Standard" (PDF). World Anti-Doping Agency. Archived from the original (PDF) on 2009-02-03. Retrieved 21 February 2009.
  15. ^ Epstein D, Dohrmann G (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. Archived from the original on April 16, 2014. Retrieved June 14, 2011.
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