Metribolone

Metribolone

Names
IUPAC name 17β-17-Hydroxy-17-methyl-estra-4,9,11-trien-3-one
Other names Methyltrienolone, R1881
Identifiers
CAS Number	965-93-5
ChEBI	CHEBI:379896
ChEMBL	ChEMBL166444
ChemSpider	229099
IUPHAR/BPS	2857
Jmol interactive 3D	Image
KEGG	C14257
MeSH	D015741
PubChem	261000
UNII	2C323EGI97
InChI InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1 Key: CCCIJQPRIXGQOE-XWSJACJDSA-N InChI=1/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1 Key: CCCIJQPRIXGQOE-XWSJACJDBS
SMILES C[C@]1(O)CC[C@]2([H])[C@]1(C)C=CC3=C4CCC(C=C4CC[C@@]23[H])=O
Properties
Chemical formula	C19H24O2
Molar mass	284.39266
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Metribolone, (also known as methyltrienolone or R1881) is a potent, non-aromatizable androgen^[1] which has also been used as a photoaffinity label for the androgen receptor.^[2] It is the 17-methylated derivative of trenbolone, and is a similarly potent anabolic steroid, but with high hepatotoxicity.^[3]

11 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.^[4]

References

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". Urol. Int. 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)". J. Steroid Biochem. 24 (1): 245–9. doi:10.1016/0022-4731(86)90058-0. PMID 2422446.
3. Krüskemper, HL; Noell, G (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. "Eleven Greek weightlifters test positive; coach suspended". Associated Press / USATODAY.com. 2008-04-04. Retrieved 2009-06-28.

External links

• Metribolone at the US National Library of Medicine Medical Subject Headings (MeSH)