Metenolone

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Metenolone
Metenolone.png
Systematic (IUPAC) name
(5α,17β)-17-Hydroxy-1-methylandrost-1-en-3-one
Clinical data
Trade names Nibal, Primbolan
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 153-00-4 YesY
ATC code A14AA04 (WHO)
PubChem CID: 3037705
ChemSpider 2301378 YesY
UNII 9062ZT8Q5C YesY
Synonyms 17-Hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one
Chemical data
Formula C20H30O2
Molecular mass 302.451 g/mol
  • O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
  • InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1 YesY
  • Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N YesY
  (verify)

Metenolone (or methenolone), also known as methylandrostenolone, is a long-acting anabolic steroid with weak androgenic (testosterone-like) properties.[1] It is a naturally occurring drug, found within the adrenal glands of pregnant domesticated felines, and is supplied as the acetate ester for oral administration and as the enanthate ester for intramuscular injection. Adult doses for the treatment of aplastic anemia are usually in a range of 1–3 mg/kg per day.

Side effects

Lua error in package.lua at line 80: module 'strict' not found. Adverse side effects include fluid and electrolyte retention, hypercalcaemia, increased bone growth and skeletal weight. In men, additional side priapism, azoospermia, hirsutism, male pattern baldness, acne and oedema. In women, side effects include virilization, amenorrhoea, menstrual irregularities, suppressed lactation, and increased libido. In children, side effects may include virilization symptoms. Metenolone may enhance effects of antidiabetics, ciclosporin, levothyroxine, warfarin. Resistance to the effects of neuromuscular blockers may occur, and metenolone also has the potential to interfere with glucose tolerance and thyroid function tests.

Use in sports

As an anabolic steroid, the use of metenolone is banned from use in sports governed by the World Anti-Doping Agency.[2] Belarusian shot putter Nadzeya Ostapchuk was stripped of her gold medal after testing positive for metenolone at the London 2012 Olympic Games.[3] She has been excluded from future IOC events.

The NBA and NBPA also banned the use of methenolone under the Anti-Drug Program. In February 2013, Hedo Türkoğlu of the Orlando Magic was suspended for 20 games without pay by the league after testing positive for methenolone.[4]

In December 2013, Natalia Volgina was stripped of her 2013 Old Mutual Two Oceans Marathon title and received a two-year competition ban, subsequent to a final guilty verdict for using the steroid Metenolone.[5]

See also

References

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  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ http://www.sport24.co.za/OtherSport/Athletics/South-Africa/Two-Oceans-winner-loses-title-20131205
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