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
Legal status
?
Identifiers
CAS number 153-00-4 YesY
ATC code A14AA04
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 
Mol. mass 302.451 g/mol
 YesY (what is this?)  (verify)

Metenolone (or methenolone) is a long-acting anabolic steroid with weak androgenic (testosterone or androsterone-like) properties. 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[edit]

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[edit]

As an anabolic steroid, the use of metenolone is banned from use in sports governed by the World Anti-Doping Agency.[1] Belarusian shot putter Nadzeya Ostapchuk was stripped of her gold medal after testing positive for metenolone at the London 2012 Olympic Games.[2] 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 suspended for 20 games without pay by the league after testing positive for methenolone.[3]

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.[4]

Synthesis[edit]

Careful investigation of the bromination reaction of 3 keto steroids, which leads ultimately to 2,4-dibromo derivatives, revealed that the sequence starts with the formation of a 2a bromo derivative, a further demonstration of the preferred enolization of the carbonyl group toward the 2 position.

Mesterolone and methenolone

Thus the treatment of Dihydrotestosterone with one equivalent of bromine under carefully controlled conditions afford 2a bromide. The bromoketone is then dehydrobrominated by means of lithium carbonate in dimethyl formamide to give the unusual enone. The conjugate addition of methyl Grignard reagent in the presence of cuprous iodide goes directly to the 1b methyl derivative mesterolone;[5] the reaction in this case goes directly to the energetically favored equatorial isomer. One of the standard methods for preparing fused cyclopropanes involved 1-3 dipolar addition of diazomethane to an olefin followed by pyrolysis of the resulting pyrrazole. The sequence follows a different pathway in the case of enones, with the pyrrazole in this case losing nitrogen so as to leave behind a new methyl group on the double bond. Thus, the dipolar addition of diazomethane to enone leads to the pyrrazole; that intermediate loses nitrogen on heating to give the 1 methyl enone, methenolone.[6]

N.B. See diagram, in final step of reaction, expected product is cyclopropane and not methylolefin.

References[edit]

  1. ^ "The World Anti-Doping Code: The 2012 Prohibited List". World Anti-Doping Agency. Retrieved 2012-05-10. 
  2. ^ "IOC withdraws gold medal from shot put athlete Nadzeya Ostapchuk". International Olympic Committee. Retrieved 13 August 2012. 
  3. ^ "Magic's Hedo Turkoglu suspended 20 games". 
  4. ^ http://www.sport24.co.za/OtherSport/Athletics/South-Africa/Two-Oceans-winner-loses-title-20131205
  5. ^ Wiechert, R.; 1968, U.S. Patent 3,361,773
  6. ^ Wiechert, R.; Kaspar, E. (1960). "Über Steroidpyrazoline und ihre Spaltung". Chemische Berichte 93 (8): 1710. doi:10.1002/cber.19600930803.  edit