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Desoxymethyltestosterone



Desoxymethyltestosterone
Systematic (IUPAC) name
(5S,8R,9S,10S,13S,14S,17S)-10,13,17-trimethyl -1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
Identifiers
CAS number 3275-64-7
ATC code  ?
PubChem 18651
Chemical data
Formula C20H32O 
Mol. mass 288.46748 g/mol
Synonyms Desoxymethyltestosterone, Madol, 17α-methyl-5α-androst-2-en-17β-ol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

X

Legal status
Routes Oral, IM, Transdermal

Desoxymethyltestosterone (Madol) is an anabolic steroid. It was one of the first "designer steroids" to be marketed as a performance-enhancing drug to athletes and bodybuilders. In animal studies it has been found to be a powerful androgen approximately half as potent as dihydrotestosterone, but caused serious side effects that are typical of 17α-alkylated steroids, such as liver damage and left ventricular hypertrophy.[1]

Additional recommended knowledge

Desoxymethyltestosterone is sometimes referred to as "DMT", though it is not the same compound as the hallucinogen Dimethyltryptamine, also known as DMT.

Desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound. It was never brought to market as commercial drug and existed only in some obscure journal articles until it was rediscovered by chemist Patrick Arnold in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte of Bay Area Laboratory Co-operative (BALCO), an American nutritional supplement company.[2]

Desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3-keto group present on nearly all commercial anabolic steroids. This does not mean it is a weak compound, and clinical research has determined that it is a fairly potent oral agent. Rat studies indicate desoxymethyltestosterone has an anabolic effect 160% that of testosterone while being only 60% as androgenic giving it a Q ratio of 6.5:1. Because of this favorable ratio, experiments in orchiectomised rats have demonstrated that treatment with desoxymethyltestosterone resulted only in a stimulation of the weight of the levator ani muscle; the prostate and seminal vesicle weights remained unaffected. In humans, this may mean that it would be less likely to cause unfavorable androgenic side effects like hair loss, acne and prostate enlargement.

Interestingly, although desoxymethyltestosterone is completely synthetic in origin, it is nearly identical in structure to delta2-androstenol, a naturally-occurring pheromone found in elephant urine.


References

  1. ^ Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Thevis M, Vollmer G, Zierau O. Characterisation of the pharmacological profile of desoxymethyltestosterone (Madol), a steroid misused for doping. Toxicology Letters. 2007 Feb 28;169(1):64-71.
  2. ^ United States Attorney for the Northern District of California (2006-08-04). "Chemist Who Created "The Clear" Sentenced". Press release. Retrieved on 2007-10-08.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Desoxymethyltestosterone". A list of authors is available in Wikipedia.
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