Chlorodehydromethyltestosterone

Chlorodehydromethyltestosterone
Clinical data
Other names	4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone
Pregnancy; category	AU: X (High risk); ;
Routes of; administration	By mouth
Drug class	Androgen; anabolic steroid
Legal status
Legal status	BR: Class C5 (Anabolic steroids); UK: Class C; US: Schedule III;
Pharmacokinetic data
Bioavailability	High
Metabolism	Liver
Elimination half-life	16 hours[citation needed]
Excretion	Urine
Identifiers
	IUPAC name 4-Chloro-17α-methylandrosta-1,4-dien-17β-ol-3-one;
CAS Number	2446-23-3 ;
PubChem CID	98521;
ChemSpider	88972 ;
UNII	ZPZ473F40K;
CompTox Dashboard (EPA)	DTXSID10179216 ;
ECHA InfoCard	100.392.451
Chemical and physical data
Formula	C20H27ClO2
Molar mass	334.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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 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 ; Key:AGUNEISBPXQOPA-XMUHMHRVSA-N ;
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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 anabolic–androgenic steroid (AAS). It is the 4-chloro-substituted derivative of metandienone (dehydromethyltestosterone).

Side effects

History

CDMT was the first original product of Jenapharm, an East German pharmaceutical company. It was patented in 1961. The idea of combining the structures of 4-chlorotestosterone (clostebol) and metandienone originated with chemist Albert Stachowiak.^{[citation needed]} At the time, this represented a unique dissociation of anabolic from androgenic 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

Doping in sports

CDMT was the key steroid administered to approximately ten thousand East German athletes as part of a secret doping program, known as State 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, the International Olympic Committee reanalyzed samples from the Beijing 2008 and London 2012 Olympic Games using the spectrometric method developed by Grigory Rodchenkov in 2011^[4] for detecting long-lasting metabolites of CDMT. Weightlifters and sprinters in particular were found to have used CDMT.

In August 2017, UFC Light Heavyweight Champion Jon Jones tested positive for turinabol following his victory over Daniel Cormier at UFC 214 the month prior.^[5]

Colorado Rockies third baseman Colton Welker tested positive in May 2021 while playing for the Triple-A Albuquerque Isotopes. He was suspended for eighty games.^{[citation needed]}

References

^ 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. Retrieved 2023-08-15.
^ 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.
^ 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 from the original on 2011-05-14. Retrieved 2009-01-04.
^ 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.
^ "Jon Jones' B sample from UFC 214 also positive for steroid turinabol". MMAJunkie.com. 13 September 2017.

[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. Retrieved 2023-08-15.

[pmid10443899-2] 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.

[CC-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 from the original on 2011-05-14. Retrieved 2009-01-04.

[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.

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