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Chlorodehydromethyltestosterone

From Wikipedia, the free encyclopedia
Chemical compound
Not to be confused withTurinal orC-DMT.
Pharmaceutical compound
Chlorodehydromethyltestosterone
Clinical data
Other names4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone
Pregnancy
category
Routes of
administration
By mouth
Drug classAndrogen;anabolic steroid
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh
MetabolismLiver
Eliminationhalf-life16 hours[citation needed]
ExcretionUrine
Identifiers
  • 4-Chloro-17α-methylandrosta-1,4-dien-17β-ol-3-one
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.392.451Edit this at Wikidata
Chemical and physical data
FormulaC20H27ClO2
Molar mass334.88 g·mol−1
3D model (JSmol)
  • O=C1\C=C/[C@]4(/C(=C1/Cl)CC[C@@H]3[C@@H]4CC[C@]2([C@H]3CC[C@@]2(O)C)C)C
  • InChI=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 checkY
  • Key:AGUNEISBPXQOPA-XMUHMHRVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Chlorodehydromethyltestosterone (CDMT; brand nameOral Turinabol), also known as4-chloro-17β-hydroxy17α-methylandrosta-1,4-dien-3-one, is ananabolic–androgenic steroid (AAS). It is the 4-chloro-substitutedderivative ofmetandienone (dehydromethyltestosterone).

Side effects

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See also:Anabolic steroid § Adverse effects

History

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CDMT was the first original product ofJenapharm, anEast Germanpharmaceutical company. It was patented in 1961. The idea of combining the structures of4-chlorotestosterone (clostebol) and metandienone originated with chemist Albert Stachowiak.[citation needed] At the time, this represented a unique dissociation ofanabolic fromandrogenic effects after oral administration.[clarification needed][2] The product was introduced for clinical use in 1965 and remained in use until 1994, when production was discontinued.[citation needed]

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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This sectionneeds additional citations forverification. Please helpimprove this article byadding citations to reliable sources in this section. Unsourced material may be challenged and removed.
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CDMT was the key steroid administered to approximately ten thousand East German athletes as part of a secret doping program, known asState Plan Topic 14.25, 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.[3]

Following allegations[by whom?] of widespread doping, theInternational Olympic Committee reanalyzed samples from theBeijing 2008 andLondon 2012 Olympic Games using thespectrometric method developed byGrigory Rodchenkov in 2011[4] for detecting long-lasting metabolites of CDMT. Weightlifters andsprinters in particular were found to have used CDMT.

In August 2017,UFC Light Heavyweight ChampionJon Jones tested positive for turinabol following his victory overDaniel Cormier atUFC 214 the month prior.[5]

Colorado Rockies third basemanColton Welker tested positive in May 2021 while playing for theTriple-AAlbuquerque Isotopes. He was suspended for eighty games.[6]

See also

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References

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  1. ^Anvisa (2023-03-31)."RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-04-04).Archived from the original on 2023-08-03. Retrieved2023-08-15.
  2. ^Schwarz S, Onken D, Schubert A (July 1999). "The steroid story of Jenapharm: from the late 1940s to the early 1970s".Steroids.64 (7):439–45.doi:10.1016/S0039-128X(99)00003-3.PMID 10443899.S2CID 40156824.
  3. ^Franke WW, Berendonk B (July 1997)."Hormonal doping and androgenization of athletes: a secret program of the German Democratic Republic government".Clin. Chem.43 (7):1262–79.doi:10.1093/clinchem/43.7.1262.PMID 9216474. Archived fromthe original on 2011-05-14. Retrieved2009-01-04.
  4. ^Sobolevsky T, Rodchenkov G (2012). "Detection and mass spectrometric characterization of novel long-term dehydrochloromethyltestosterone metabolites in human urine".The Journal of Steroid Biochemistry and Molecular Biology.128 (3–5):121–7.doi:10.1016/j.jsbmb.2011.11.004.PMID 22142641.S2CID 42460280.
  5. ^"Jon Jones' B sample from UFC 214 also positive for steroid turinabol".MMAJunkie.com. 13 September 2017.
  6. ^Byrne, Connor (May 6, 2021)."Rockies' Colton Welker Receives 80-Game Suspension".MLB Trade Rumors. Retrieved8 November 2025.
Androgens
(incl.AASTooltip anabolic–androgenic steroid)
ARTooltip Androgen receptoragonists
Progonadotropins
Antiandrogens
ARTooltip Androgen receptorantagonists
Steroidogenesis
inhibitors
5α-Reductase
Others
Antigonadotropins
Others
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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