Clinical data
Routes of
Synonyms Methyltrienolone, 17α-Methyltrenbolone; R-1881; RU-1881; NSC-92858; 17α-Methyl-19-nor-Δ9,11-testosterone; 17α-Methylestra-4,9,11-trien-17β-ol-3-one
CAS Number 965-93-5 YesY
PubChem (CID) 261000
ChemSpider 229099 N
KEGG C14257 N
ChEBI CHEBI:379896 N
Chemical and physical data
Formula C19H24O2
Molar mass 284.393 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Metribolone (INN) (developmental code names R-1881 (or RU-1881), NSC-92858), also known as methyltrienolone (or 17α-methyltrenbolone), as well as 17α-methyl-19-nor-Δ9,11-testosterone or 17α-methyl-19-norandrosta-4,9,11-triene-17β-ol-3-one, is a highly potent, orally active, non-aromatizable anabolic-androgenic steroid (AAS)[1] of the 19-nortestosterone and 17α-alkylated groups which was never marketed for clinical use but has been used in scientific research as a photoaffinity label for the androgen receptor (AR) and in AR ligand binding assays.[2] It is the 17α-methylated derivative of trenbolone (trienolone), and is a similarly potent AAS, but has a high potential for hepatotoxicity similarly to other 17α-alkylated AAS.[3] Metribolone binds with high affinity not only to the AR but also to the progesterone receptor (PR), and binds to the glucocorticoid receptor (GR) as well.[4][5] It is said to be the most potent AAS.[6]

Eleven members of the Greek national weightlifting team and 4 Greek track and field athletes tested positive with methyltrienolone prior to the 2008 Beijing Olympic Games.[7]

See also


  1. Bojar H, Maar K, Staib W (1980). "The endocrine background of human renal cell carcinoma. V. Binding of the highly potent androgen methyltrienolone (R 1881) by tumour cytosol". Urologia Internationalis. 35 (2): 154–60. doi:10.1159/000280315. PMID 6966435.
  2. Brinkmann AO, Kuiper GG, de Boer W, Mulder E, Bolt J, van Steenbrugge GJ, van der Molen HJ (January 1986). "Characterization of androgen receptors after photoaffinity labelling with [3H]methyltrienolone (R1881)". Journal of Steroid Biochemistry. 24 (1): 245–9. doi:10.1016/0022-4731(86)90058-0. PMID 2422446.
  3. Krüskemper HL, Noell G (July 1966). "Liver toxicity of a new anabolic agent: methyltrienolone (17-alpha-methyl-4,9,11-estratriene-17 beta-ol-3-one)". Steroids. 8 (1): 13–24. doi:10.1016/0039-128x(66)90114-0. PMID 5955468.
  4. Singh SM, Gauthier S, Labrie F (February 2000). "Androgen receptor antagonists (antiandrogens): structure-activity relationships". Current Medicinal Chemistry. 7 (2): 211–47. doi:10.2174/0929867003375371. PMID 10637363.
  5. Ho-Kim MA, Tremblay RR, Dubé JY (November 1981). "Binding of methyltrienolone to glucocorticoid receptors in rat muscle cytosol". Endocrinology. 109 (5): 1418–23. doi:10.1210/endo-109-5-1418. PMID 6975208.
  6. Schneider G, Kiss A, Mernyák E, Benke Z, Wölfling J, Frank É, Bózsity N, Gyovai A, Minorics R, Zupkó I (2016). "Stereocontrolled synthesis of the four 16-hydroxymethyl-19-nortestosterone isomers and their antiproliferative activities". Steroids. 105: 113–20. doi:10.1016/j.steroids.2015.12.003. PMID 26686898.
  7. "Eleven Greek weightlifters test positive; coach suspended". Associated Press / 2008-04-04. Retrieved 2009-06-28.

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