desoxymethyltestosterone

{{See also|Anabolic steroid#Adverse effects}}

In animal studies, desoxymethyltestosterone has been found to bind to the androgen receptor (AR) about half as strongly as DHT, and to cause side effects that are typical of 17α-alkylated AAS, such as liver damage and left ventricular hypertrophy when taken in higher doses.{{cite journal | vauthors = Diel P, Friedel A, Geyer H, Kamber M, Laudenbach-Leschowsky U, Schänzer W, Thevis M, Vollmer G, Zierau O | title = Characterisation of the pharmacological profile of desoxymethyltestosterone (Madol), a steroid misused for doping | journal = Toxicol. Lett. | volume = 169 | issue = 1 | pages = 64–71 | year = 2007 | pmid = 17254722 | doi = 10.1016/j.toxlet.2006.12.004 }}

Desoxymethyltestosterone is unusual in that it is structurally a 2-ene compound, lacking the 3-keto group present in almost all commercial AAS (with ethylestrenol 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. 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.{{cite journal | vauthors = Edwards JA, Bowers A | title = Delta-2-Hormone Analogues | journal = Chemistry and Industry | date = January 1961 | issue = 48 | pages = 1962–63}} Because of this favorable ratio, experiments in orchiectomized 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 leading the authors of one study to characterize desoxymethyltestosterone as a powerful AAS with attributes of a selective androgen receptor modulator (SARM) and some indication of toxicity.

{{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 a synthetic androstane steroid and a 17α-alkylated derivative of dihydrotestosterone (DHT).

Desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound the same year. It was described in the scientific literature in 1963. However, it was never brought to market as a commercial drug.{{US patent|2996524}} Desoxymethyltestosterone was rediscovered by chemist, AAS enthusiast, and amateur bodybuilder 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 and steroid supplier.{{cite press release |url=http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%20press.htm |title=Chemist Who Created "The Clear" Sentenced |publisher=United States Attorney for the Northern District of California |date=2006-08-04 |access-date=2007-10-08 |url-status=dead |archive-url=https://web.archive.org/web/20061014084938/http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%20press.htm |archive-date=2006-10-14 }}

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 along with boldione and dienedione.{{Cite web |url=http://www.deadiversion.usdoj.gov/fed_regs/rules/2008/fr0425.htm |title=Rules – 2008 – Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act |access-date=2008-05-06 |archive-date=2010-01-13 |archive-url=https://web.archive.org/web/20100113023637/http://www.deadiversion.usdoj.gov/fed_regs/rules/2008/fr0425.htm |url-status=dead }}{{Cite web |url=http://edocket.access.gpo.gov/2008/E8-8842.htm |title=FR Doc E8-8842 |access-date=2008-05-06 |archive-url=https://web.archive.org/web/20080505045134/http://edocket.access.gpo.gov/2008/E8-8842.htm |archive-date=2008-05-05 |url-status=dead }}{{Cite web |url=http://drugtopics.modernmedicine.com/drugtopics/article/articleDetail.jsp?id=512638 |title=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 |access-date=2008-05-06 |archive-url=https://web.archive.org/web/20080502193813/http://drugtopics.modernmedicine.com/drugtopics/article/articleDetail.jsp?id=512638 |archive-date=2008-05-02 |url-status=dead }}{{Cite web |url=http://www.tradingmarkets.com/.site/news/Stock%20News/1438704/ |title=Classification of Three Steroids as Schedule III Anabolic Steroids Under the Controlled Substances Act |access-date=2008-05-02 |archive-url=https://web.archive.org/web/20080706042514/http://www.tradingmarkets.com/.site/news/Stock%20News/1438704/ |archive-date=2008-07-06 |url-status=dead }} The substance had come under scrutiny after it was found to be present in several over-the-counter bodybuilding supplements.{{cite journal | vauthors = Okano M, Sato M, Ikekita A, Kageyama S | title = Analysis of non-ketoic steroids 17alpha-methylepithiostanol and desoxymethyl- testosterone in dietary supplements | journal = Drug Testing and Analysis | volume = 1 | issue = 11–12 | pages = 518–25 | date = November 2009 | pmid = 20355167 | doi = 10.1002/dta.72 }}

• 5α-Androst-2-en-17-one

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{{Androgen receptor modulators}}

Category:Abandoned drugs

Category:1-Methylcyclopentanols

Category:Anabolic–androgenic steroids

Category:Androstanes

Category:Designer drugs

Category:Hepatotoxins