Chlorodehydromethyltestosterone

Chlorodehydromethyltestosterone
Clinical data
Other names	4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone
Pregnancy; category	AU: X (High risk) ; US: X (Contraindicated) ;
Routes of; administration	By mouth
Drug class	Androgen; anabolic steroid
Legal status
Legal status	UK: Class C ; US: Schedule III ;
Pharmacokinetic data
Bioavailability	High
Metabolism	Liver
Elimination half-life	16 hours
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 ;
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

Chlorodehydromethyltestosterone

History

CDMT was the first original product of Jenapharm, an East German pharmaceutical company. The patent registration took place in 1961. The idea of combining the structures of 4-chlorotestosterone (clostebol) and metandienone originated from the chemist Albert Stachowiak. At the time this represented a unique dissociation of anabolic and androgenic effects after oral administration.[1] The product had been introduced for clinical use from 1965 until 1994 when its production was discontinued.

Society and culture

Doping in sports

CDMT was the key steroid administered to approximately 10,000 athletes from East Germany (GDR) as secret official policy, often without their knowing the nature of the "vitamins" they were forced to take. The doping program was run by the East German Government from about 1968 until 1989 when the GDR collapsed. The doping program was known as State Plan Topic 14.25. The doping was done in secret; it was only in the 1990s that Franke and Berendonk looked closely at the original archived information and discovered the true scope of just how well-planned and successful the doping regime had been (in terms of medal success and world record performances).[2]

Following allegations by the German documentary of widespread doping the IOC kicked off a reanalysis of Beijing 2008 and London 2012 samples for all sports.

Weightlifters and sprinters in particular were found to have used CDMT. Most of the doped athletes coming from Russia, Ukraine, and Belarus.[3] However, the method developed by Grigory Rodchenkov in 2011[4] was used in 2016 to detect long-term metabolites of CDMT while retesting the athletes' Olympic samples.

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References

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.
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.
"Retests of Olympic Doping Samples *15 More Positives from 2008 Announced* - All Things Gym". All Things Gym. 2016-09-09. Retrieved 2016-12-31.
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.

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[pmid10443899-1] 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.

[CC-2] 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.

[3] "Retests of Olympic Doping Samples *15 More Positives from 2008 Announced* - All Things Gym". All Things Gym. 2016-09-09. Retrieved 2016-12-31.

[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.