Desoxymethyltestosterone

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Desoxymethyltestosterone
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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
Clinical data
Pregnancy
category
  • X
Routes of
administration		 Oral, IM, Transdermal
Legal status
Legal status
Identifiers
CAS Number 3275-64-7
ATC code none
PubChem CID 18651
Synonyms Desoxymethyltestosterone, Madol, Pheraplex, 17α-methyl-5α-androst-2-en-17β-ol
Chemical data
Formula C20H32O
Molar mass 288.46748 g/mol[[Script error: No such module "String".]]
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Desoxymethyltestosterone (Madol, Pheraplex) 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 bind to the androgen receptor about as half as strongly as dihydrotestosterone, and caused side effects that are typical of 17α-alkylated steroids, such as liver damage when taken in higher dosages and left ventricular hypertrophy.[1]

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 a 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.[3] 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.[4] 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[5]. 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 produced by elephants and other mammals.

DMT became a controlled substance in the US on January 4, 2010, and is classified as a Schedule III anabolic steroid under the United States Controlled Substances Act.[6][7][8][9] The substance had come under scrutiny after it was found to be present in several over-the-counter bodybuilding supplements.

References

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Anabolic steroids (A14) (tradename in brackets)
Androstane (carbon 19 present)
Adrenosterone • Androisoxazole • Bolasterone (Myagen) • Bolazine • Boldione • Boldenone undecylenate (Equipoise) • 4-Chlordehydromethyltestosterone (Turinabol) • 4-Hydroxytestosterone • Calusterone • Clostebol • Danazol • Desoxymethyltestosterone (Madol) • DHT • Drostanolone (Masteron) • Enestebol • Epitiostanol • Fluoxymesterone (Halotestin) • Formebolone • Furazabol (Miotolan) • Hydroxystenozole • Mebolazine • Mesabolone • Mestanolone • Mesterolone (Proviron) • Methandriol • Methandrostenolone (Dianabol) • Methenolone • Methenolone enanthate (Primobolan) • Methasterone (Superdrol) • Methyltestosterone • Oxandrolone (Anavar) • Oxymetholone (Anadrol) • Oxymesterone • Prostanozol • Quinbolone (Anabolicum Vister) • Roxibolone • Silandrone • Stanozolol (Strombafort, Winstrol) • Stenbolone • Testosterone`s (Sustamed, Sustanon) • 1-Testosterone • Thiomesterone • Trestolone
Estrene (carbon 19 absent)
Prohormones
de:Desoxymethyltestosteron hu:Dezoximetiltesztoszteron
  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. ↑ "Chemist Who Created "The Clear" Sentenced" (Press release). United States Attorney for the Northern District of California. 2006-08-04. http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%20press.htm. Retrieved 2007-10-08. 
  3. ↑ http://www.ncbi.nlm.nih.gov/pubmed/17254722
  4. ↑ Edwards J.A. and Bowers A. Chemistry and Industry (1961) 1962-63.
  5. ↑ http://www.ncbi.nlm.nih.gov/pubmed/17254722
  6. ↑ Rules - 2008 - Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act
  7. ↑ FR Doc E8-8842
  8. ↑ DEA proposes listing three steroids under Schedule III - Since three steroids have a high potential for drug abuse and trafficking, the Drug Enforcement Administration wants to classify them as Schedu
  9. ↑ Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act
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