Metenolone

Metenolone

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	A14AA04 (WHO)
Legal status
Legal status	CA: Schedule IV
Identifiers
IUPAC name (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms	Methenolone; Methylandrostenolone; 1-Methyl-5α-androst-1-en-17β-ol-3-one; 1-Methyl-4,5α-dihydro-δ^1-testosterone; 1-Methyl-δ^1-DHT
CAS Number	153-00-4
PubChem (CID)	3037705
ChemSpider	2301378
UNII	9062ZT8Q5C
Chemical and physical data
Formula	C20H30O2
Molar mass	302.451 g/mol
3D model (Jmol)	Interactive image
SMILES 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 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 Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N
(verify)

Metenolone (brand names Primobolan, Nibal) or methenolone, also known as methylandrostenolone, as well as 1-methyl-4,5α-dihydro-δ¹-testosterone (1-methyl-δ¹-DHT) or as 1-methyl-5α-androst-1-en-17β-ol-3-one, is a long-acting anabolic-androgenic steroid (AAS) that is marketed for medical use.^[1] It is a naturally occurring steroid, found within the adrenal glands of pregnant domesticated felines. Metenolone itself is not used in medicine; as a pharmaceutical drug, it is supplied as metenolone acetate for oral administration and as metenolone enanthate for depot intramuscular injection.^[2] Adult doses for the treatment of aplastic anemia are usually in a range of 1–3 mg/kg per day.

Side effects

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 AAS, the use of metenolone is banned from use in sports governed by the World Anti-Doping Agency.^[3] Belarusian shot putter Nadzeya Ostapchuk was stripped of her gold medal after testing positive for metenolone at the London 2012 Olympic Games.^[4]

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.^[5]

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 metenolone.^[6]

See also

• Drostanolone
• Mesterolone
• Stenbolone

References

1. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 660–. ISBN 978-3-88763-075-1.
2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 660–. ISBN 978-3-88763-075-1.
3. "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2012-05-10.
4. "IOC withdraws gold medal from shot put athlete Nadzeya Ostapchuk". International Olympic Committee. Retrieved 13 August 2012.
5. "Magic's Hedo Turkoglu suspended 20 games".
6. http://www.sport24.co.za/OtherSport/Athletics/South-Africa/Two-Oceans-winner-loses-title-20131205