| Revision as of 18:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 471256548 of page 4-Chlorodehydromethyltestosterone for the Chem/Drugbox validation project (updated: 'CAS_number'). |
Latest revision as of 09:37, 4 November 2024 edit 203.170.73.62 (talk)No edit summaryTag: references removed |
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{{Short description|Chemical compound}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Distinguish|Turinal}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = 416242965 |
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| Watchedfields = changed |
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| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopentaphenanthren-3-one |
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| verifiedrevid = 477221278 |
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| image = 4-Chlorodehydromethyltestosterone.png |
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| IUPAC_name = 4-Chloro-17α-methylandrosta-1,4-dien-17β-ol-3-one |
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| image = Chlorodehydromethyltestosterone.svg |
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| width = 225px |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| pregnancy_US = X |
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| pregnancy_category = X (])<br/>X (]) |
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| pregnancy_AU = X |
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| legal_status = ] (]) <br/> ] (]) |
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| legal_BR = C5 |
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| routes_of_administration = Oral |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_US = Schedule III |
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| legal_UK = Class C |
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| routes_of_administration = ] |
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| class = ]; ] |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| bioavailability = 100% Oral |
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| bioavailability = High |
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| metabolism = ] |
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| metabolism = ] |
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| elimination_half-life = 16 hours |
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| elimination_half-life = 16 hours{{Citation needed|date=November 2017}} |
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| excretion = Undocumented |
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| excretion = ] |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|changed|??}} |
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| CAS_number = <!-- blanked - oldvalue: 2446-23-3 --> |
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| CAS_number = 2446-23-3 |
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| PubChem = 98521 |
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| PubChem = 98521 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = ZPZ473F40K |
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| ChemSpiderID = 88972 |
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| ChemSpiderID = 88972 |
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| synonyms = <small>4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone</small> |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=20 | H=27 | Cl=1 | O=2 |
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| C=20 | H=27 | Cl=1 | O=2 |
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| SMILES = O=C1\C=C/4(/C(=C1/Cl)CC34CC2(3CC2(O)C)C)C |
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| molecular_weight = 334.8854 |
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| smiles = O=C1\C=C/4(/C(=C1/Cl)CC34CC2(3CC2(O)C)C)C |
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| InChI = 1/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1 |
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| InChIKey = AGUNEISBPXQOPA-XMUHMHRVBK |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1 |
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| StdInChI = 1S/C20H27ClO2/c1-18-9-8-16(22)17(21)15(18)5-4-12-13(18)6-10-19(2)14(12)7-11-20(19,3)23/h8-9,12-14,23H,4-7,10-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1 |
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| StdInChIKey = AGUNEISBPXQOPA-XMUHMHRVSA-N |
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| StdInChIKey = AGUNEISBPXQOPA-XMUHMHRVSA-N |
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}} |
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'''Chlorodehydromethyltestosterone''' ('''CDMT'''; brand name '''Oral Turinabol'''), also known as '''4-chloro-17β-hydroxy17α-methylandrosta-1,4-dien-3-one''', is an ] (AAS). It is the 4-chloro-substituted ] of ] (dehydromethyltestosterone). |
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==Side effects== |
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{{See also|Anabolic steroid#Adverse effects}} |
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==History== |
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CDMT was the first original product of ], an ] ]. It was patented in 1961. The idea of combining the structures of ] (clostebol) and metandienone originated with chemist Albert Stachowiak.{{Citation needed|date=July 2012}} At the time, this represented a unique dissociation of ] from ]ic effects after oral administration.{{clarify|date=September 2021}}<ref name="pmid10443899">{{cite journal |vauthors =Schwarz S, Onken D, Schubert A |title=The steroid story of Jenapharm: from the late 1940s to the early 1970s |journal=Steroids |volume=64 |issue=7 |pages=439–45 |date=July 1999 |pmid=10443899 |doi=10.1016/S0039-128X(99)00003-3 |s2cid=40156824 }}</ref> The product was introduced for clinical use in 1965 and remained in use until 1994, when production was discontinued.{{cn|date=September 2021}} |
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==Society and culture== |
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===Doping in sports=== |
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{{see also|Doping at the Olympic Games}} |
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{{More citations needed|section |date=January 2012}} |
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CDMT was the key steroid administered to approximately ten thousand ] athletes as part of a secret doping program, known as ], often without them knowing the nature of the "vitamins" they were forced to take. The program remained in place from about 1968 until the collapse of the German Democratic Republic in 1989. In the 1990s, Franke and Berendonk examined GDR archives to elucidate the expansive scope of this operation, which had resulted in numerous medal wins and world-record performances.<ref name=CC>{{cite journal |vauthors=Franke WW, Berendonk B |title=Hormonal doping and androgenization of athletes: a secret program of the German Democratic Republic government |journal=Clin. Chem. |volume=43 |issue=7 |pages=1262–79 |date=July 1997 |pmid=9216474 |doi=10.1093/clinchem/43.7.1262 |url=http://www.clinchem.org/cgi/content/full/43/7/1262 |doi-access=free |access-date=2009-01-04 |archive-url=https://web.archive.org/web/20110514103044/http://www.clinchem.org/cgi/content/full/43/7/1262 |archive-date=2011-05-14 |url-status=dead }}</ref> |
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Following allegations{{by whom|date=September 2021}} of widespread doping, the ] reanalyzed samples from the ] and ] using the ] method developed by ] in 2011<ref>{{cite journal |vauthors=Sobolevsky T, Rodchenkov G |title=Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine |journal=The Journal of Steroid Biochemistry and Molecular Biology |volume=128 |issue=3–5 |pages=121–7 |year=2012 |pmid=22142641 |doi=10.1016/j.jsbmb.2011.11.004 |s2cid=42460280 }}</ref> for detecting long-lasting metabolites of CDMT. ] and ]s in particular were found to have used CDMT. |
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In August 2017, ] ] tested positive for turinabol following his victory over ] at ] the month prior.<ref>{{cite web|url=https://mmajunkie.usatoday.com/2017/09/jon-jones-b-sample-steroid-turinabol-positive-ufc-215-usada/amp|title=Jon Jones' B sample from UFC 214 also positive for steroid turinabol|work=MMAJunkie.com|date=13 September 2017}}</ref> |
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] third baseman ] tested positive in May 2021 while playing for the ] ]. He was suspended for eighty games.{{cn|date=September 2021}} |
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==See also== |
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* ] |
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* ] |
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==References== |
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{{Reflist|2}} |
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{{Androgens and antiandrogens}} |
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{{Androgen receptor modulators}} |
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] |
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] |
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] |
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] |
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] |
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] |