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{{short description|Chemical compound}}
{{drugbox | verifiedrevid = 399891863
{{Drugbox
|
| Watchedfields = changed
| IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthren-17-ol
| verifiedrevid = 411618770
| image = Desoxymethyltestosterone.png
| IUPAC_name = (5''S'',8''R'',9''S'',10''S'',13''S'',14''S'',17''S'')-10,13,17-trimethyl-1,4,5,6,7,8,9,11,12,14,15,16-dodecahydrocyclopentaphenanthren-17-ol
| width = 200
| image = Desoxymethyltestosterone.svg
| width = 200px

<!--Clinical data-->
| tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = X
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = Class C<ref>{{Cite web |url=https://www.criminallawandjustice.co.uk/features/Misuse-Drugs-Legislation |title=Misuse of Drugs Legislation }}{{Dead link|date=January 2024 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
| legal_US = Schedule III
| legal_status =
| routes_of_administration = ]
| class = ]; ]

<!--Pharmacokinetic data-->
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 3275-64-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B9E9G5A169
| ATC_prefix = None
| ATC_suffix =
| PubChem = 18651
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17611 | ChemSpiderID = 17611
| synonyms = DMT; Madol; Pheraplex; 3-Desoxy-17α-methyl-δ<sup>2</sup>-5α-dihydrotestosterone; 3-Desoxy-17α-methyl-δ<sup>2</sup>-DHT; 17α-Methyl-5α-androst-2-en-17β-ol; NSC-63329; SC-11977
| InChI = 1/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

| InChIKey = FRVHJVATKMIOPQ-PAPWGAKMBS
<!--Chemical data-->
| smiles = O4(2((1CC3(1CC2)(C)C\C=C/C3)CC4)C)C
| C=20 | H=32 | O=1
| SMILES = O4(2((1CC3(1CC2)(C)C\C=C/C3)CC4)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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 | StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FRVHJVATKMIOPQ-PAPWGAKMSA-N | StdInChIKey = FRVHJVATKMIOPQ-PAPWGAKMSA-N
| CAS_number = 3275-64-7
| synonyms = Desoxymethyltestosterone; Madol; Pheraplex; 17α-Methyl-5α-androst-2-en-17β-ol
| ATC_prefix = none
| ATC_suffix =
| PubChem = 18651
| DrugBank =
| C=20 | H=32 | O=1
| molecular_weight = 288.46748 g/mol
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category= X
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->
| legal_US =
| legal_status = ] (])
| routes_of_administration = Oral, IM, Transdermal
}} }}


'''Desoxymethyltestosterone''' ('''DMT'''), known by the nicknames '''Madol''' and '''Pheraplex''', is a ] and ] ] (AAS) and a ] ] of ] (DHT) which was never marketed for medical use. It was one of the first ]s to be marketed as a ] to ]s and ]s.
'''Desoxymethyltestosterone''' ('''Madol''', '''Pheraplex''') is an ]. It was one of the first "designer steroids" to be marketed as a ] to athletes and bodybuilders. In animal studies it has been found to bind to the androgen receptor about as half as strongly as ], and caused side effects that are typical of 17α-alkylated steroids, such as ] when taken in higher dosages and ].<ref name=Diel>{{cite journal | doi = 10.1016/j.toxlet.2006.12.004 | author = 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=Toxicology Letters | year=2007 |volume=169 | issue = 1 | pages = 64–71 | pmid = 17254722}}</ref>

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

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

==Pharmacology==

===Pharmacodynamics===
In animal studies, desoxymethyltestosterone has been found to bind to the ] (AR) about half as strongly as DHT, and to cause ]s that are typical of 17α-alkylated AAS, such as ] and ] when taken in higher doses.<ref name="pmid17254722">{{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 }}</ref>

Desoxymethyltestosterone is unusual in that it is structurally a 2-] compound, lacking the 3-] group present in almost all commercial AAS (with ] 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.<ref name="pmid17254722" /> 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.<ref>{{cite journal | vauthors = Edwards JA, Bowers A | title = Delta-2-Hormone Analogues | journal = Chemistry and Industry | date = January 1961 | issue = 48 | pages = 1962–63}}</ref> Because of this favorable ratio, experiments in ] rats have demonstrated that treatment with desoxymethyltestosterone resulted only in a stimulation of the weight of the levator ani muscle; the ] and ] weights remained unaffected leading the authors of one study to characterize desoxymethyltestosterone as a powerful AAS with attributes of a ] (SARM) and some indication of ].<ref name="pmid17254722" />

==Chemistry==
{{See also|List of androgens/anabolic steroids}}


Desoxymethyltestosterone, also known as 3-desoxy-17α-methyl-δ<sup>2</sup>-5α-dihydrotestosterone (3-desoxy-17α-methyl-δ<sup>2</sup>-DHT) or as 17α-methyl-5α-androst-2-en-17β-ol, is a ] ] ] and a ] ] of ] (DHT).
Desoxymethyltestosterone is sometimes referred to as "DMT", though it is not the same compound as the hallucinogen ], also known as DMT.


==History==
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. It was rediscovered by chemist ] in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte of ] (BALCO), an American nutritional supplement company and steroid supplier.<ref>{{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 |accessdate=2007-10-08}}</ref>
Desoxymethyltestosterone was invented in 1961 by Max Huffman who obtained a patent on the compound the same year.<ref name="pmid17254722" /> It was described in the scientific literature in 1963.<ref name="pmid17254722" /> However, it was never brought to market as a commercial drug.<ref>{{US patent|2996524}}</ref><ref name="pmid17254722" /> Desoxymethyltestosterone was rediscovered by chemist, AAS enthusiast, and amateur bodybuilder ] in 2005. Arnold produced desoxymethyltestosterone and supplied it to Victor Conte of ] (BALCO), an American nutritional supplement company and steroid supplier.<ref>{{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 }}</ref>


DMT became a controlled substance in the US on January 4, 2010, and is classified as a ] ] under the United States ] along with ] and ].<ref>{{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<!-- Bot generated title --> |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 }}</ref><ref>{{Cite web |url=http://edocket.access.gpo.gov/2008/E8-8842.htm |title=FR Doc E8-8842<!-- Bot generated title --> |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 }}</ref><ref>{{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<!-- Bot generated title --> |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 }}</ref><ref>{{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<!-- Bot generated title --> |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 }}</ref> The substance had come under scrutiny after it was found to be present in several over-the-counter ].<ref>{{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 }}</ref>
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.<ref name=Diel/> 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.<ref>{{cite journal | author = Edwards J.A. and Bowers A. | journal = Chemistry and Industry | year = 1961 | pages = 1962–63}}</ref> 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.<ref name=Diel/> Toxic side effects including stimulation of gene expression in the liver and increase of heart weight were also observed.<ref name=Diel/>


==See also==
DMT became a controlled substance in the US on January 4, 2010, and is classified as a ] ] under the United States ] along with ] and ].<ref></ref><ref></ref><ref></ref><ref></ref> The substance had come under scrutiny after it was found to be present in several over-the-counter ].
* ]


==References== ==References==
{{Reflist}} {{Reflist|2}}


{{Anabolic steroids}}


{{Androgen receptor modulators}}
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