Chlorodehydromethyltestosterone

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).

Not to be confused with Turinal.
Chlorodehydromethyltestosterone
Clinical data
Other names4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone
Pregnancy
category
  • AU: X (High risk)
Routes of
administration		By mouth
Drug classAndrogen; anabolic steroid
Legal status
Legal status
Pharmacokinetic data
BioavailabilityHigh
MetabolismLiver
Elimination half-life16 hours
ExcretionUrine
Identifiers
IUPAC name
  • 4-Chloro-17α-methylandrosta-1,4-dien-17β-ol-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H27ClO2
Molar mass334.88 g·mol−1
3D model (JSmol)
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 Y
  • Key:AGUNEISBPXQOPA-XMUHMHRVSA-N Y
 NY (what is this?)  (verify)

Side effects
See also: Anabolic steroid § Adverse effects
  • Chlorodehydromethyltestosterone

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. At the time, this represented a unique dissociation of anabolic from androgenic effects after oral administration.[1] The product was introduced for clinical use in 1965 and remained in use until 1994, when production was discontinued.

Society and culture

Doping in sports
See also: Doping at the Olympic Games

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 their 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.[2]

Following allegations 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[3] for detecting long-lasting metabolites of CDMT. Weightlifters and sprinters in particular were found to have used CDMT. Most of the doped athletes came from Russia, Ukraine, and Belarus.[4]

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.

See also

References
  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. S2CID 40156824.
  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. 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.
  4. "Retests of Olympic Doping Samples *15 More Positives from 2008 Announced* - All Things Gym". All Things Gym. 2016-09-09. Retrieved 2016-12-31.
  5. "Jon Jones' B sample from UFC 214 also positive for steroid turinabol". MMAJunkie.com. 13 September 2017.
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