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Desoxymethyltestosterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Desoxymethyltestosterone
Clinical data
Other namesDMT; Madol; Pheraplex; 3-Desoxy-17α-methyl-δ2-5α-dihydrotestosterone; 3-Desoxy-17α-methyl-δ2-DHT; 17α-Methyl-5α-androst-2-en-17β-ol; NSC-63329; SC-11977
Pregnancy
category
  • X
Routes of
administration
By mouth
Drug classAndrogen;Anabolic steroid
ATC code
  • None
Legal status
Legal status
Identifiers
  • (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
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC20H32O
Molar mass288.475 g·mol−1
3D model (JSmol)
  • O[C@@]4([C@@]2([C@H]([C@@H]1CC[C@@H]3[C@]([C@H]1CC2)(C)C\C=C/C3)CC4)C)C
  • InChI=1S/C20H32O/c1-18-11-5-4-6-14(18)7-8-15-16(18)9-12-19(2)17(15)10-13-20(19,3)21/h4-5,14-17,21H,6-13H2,1-3H3/t14-,15-,16+,17+,18+,19+,20+/m1/s1 checkY
  • Key:FRVHJVATKMIOPQ-PAPWGAKMSA-N checkY
  (verify)

Desoxymethyltestosterone (DMT), known by the nicknamesMadol andPheraplex, is asynthetic andorally activeanabolic–androgenic steroid (AAS) and a17α-methylatedderivative ofdihydrotestosterone (DHT) which was never marketed for medical use. It was one of the firstdesigner steroids to be marketed as aperformance-enhancing drug toathletes andbodybuilders.

Desoxymethyltestosterone is sometimes abbreviated as DMT, though it should not be confused with thehallucinogendimethyltryptamine, which is also known by the same acronym.

Side effects

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See also:Anabolic steroid § Adverse effects

Pharmacology

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Pharmacodynamics

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In animal studies, desoxymethyltestosterone has been found to bind to theandrogen receptor (AR) about half as strongly as DHT, and to causeside effects that are typical of 17α-alkylated AAS, such asliver damage andleft ventricular hypertrophy when taken in higher doses.[2]

Desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3-keto group present in almost all commercial AAS (withethylestrenol being a rare and notable exception). This does not mean it is a weak compound, and clinical research has determined that it is a fairly potent oral agent.[2] Rat studies indicate that desoxymethyltestosterone has an anabolic effect 160% that of testosterone while being only 60% as androgenic, giving it a Q ratio of 6.5:1.[3] Because of this favorable ratio, experiments inorchiectomized rats have demonstrated that treatment with desoxymethyltestosterone resulted only in a stimulation of the weight of the levator ani muscle; theprostate andseminal vesicle weights remained unaffected leading the authors of one study to characterize desoxymethyltestosterone as a powerful AAS with attributes of aselective androgen receptor modulator (SARM) and some indication oftoxicity.[2]

Chemistry

[edit]
See also:List of androgens/anabolic steroids

Desoxymethyltestosterone, also known as 3-desoxy-17α-methyl-δ2-5α-dihydrotestosterone (3-desoxy-17α-methyl-δ2-DHT) or as 17α-methyl-5α-androst-2-en-17β-ol, is asyntheticandrostanesteroid and a17α-alkylatedderivative ofdihydrotestosterone (DHT).

History

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Desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound the same year.[2] It was described in the scientific literature in 1963.[2] However, it was never brought to market as a commercial drug.[4][2] Desoxymethyltestosterone was rediscovered by chemist, AAS enthusiast, and amateur bodybuilderPatrick Arnold in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte ofBay Area Laboratory Co-operative (BALCO), an American nutritional supplement company and steroid supplier.[5]

DMT became a controlled substance in the US on January 4, 2010, and is classified as aSchedule IIIanabolic steroid under the United StatesControlled Substances Act along withboldione anddienedione.[6][7][8][9] The substance had come under scrutiny after it was found to be present in several over-the-counterbodybuilding supplements.[10]

See also

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References

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  1. ^"Misuse of Drugs Legislation".[permanent dead link]
  2. ^abcdefDiel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Thevis M, Vollmer G, Zierau O (2007). "Characterisation of the pharmacological profile of desoxymethyltestosterone (Madol), a steroid misused for doping".Toxicol. Lett.169 (1):64–71.doi:10.1016/j.toxlet.2006.12.004.PMID 17254722.
  3. ^Edwards JA, Bowers A (January 1961). "Delta-2-Hormone Analogues".Chemistry and Industry (48):1962–63.
  4. ^U.S. patent 2,996,524
  5. ^"Chemist Who Created "The Clear" Sentenced" (Press release). United States Attorney for the Northern District of California. 2006-08-04. Archived fromthe original on 2006-10-14. Retrieved2007-10-08.
  6. ^"Rules – 2008 – Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". Archived fromthe original on 2010-01-13. Retrieved2008-05-06.
  7. ^"FR Doc E8-8842". Archived fromthe original on 2008-05-05. Retrieved2008-05-06.
  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". Archived fromthe original on 2008-05-02. Retrieved2008-05-06.
  9. ^"Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act". Archived fromthe original on 2008-07-06. Retrieved2008-05-02.
  10. ^Okano M, Sato M, Ikekita A, Kageyama S (November 2009). "Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements".Drug Testing and Analysis.1 (11–12):518–25.doi:10.1002/dta.72.PMID 20355167.


ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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