Chemistry:Chlorodehydromethyltestosterone

Short description: Chemical compound

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	BR: Class C5 (Anabolic steroids) 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 N
PubChem CID	98521
ChemSpider	88972 Y
UNII	ZPZ473F40K
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 Y Key:AGUNEISBPXQOPA-XMUHMHRVSA-N Y
NY (what is this?)  (verify)

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).

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. 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

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.

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 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.

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.

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

• Chlorodehydromethylandrostenediol
• Chloromethylandrostenediol

References

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| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
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| group1 = Androgens
(incl. AAS)

| list1 =

AR agonists

Testosterone derivatives: Androstenediol dipropionate Boldenone undecylenate Clostebol Clostebol acetate Clostebol caproate Clostebol propionate Cloxotestosterone acetate Prasterone (dehydroepiandrosterone, DHEA) Prasterone enanthate (DHEA enanthate) Prasterone sulfate (DHEA sulfate) Quinbolone Testosterone# Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot)) Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT) Androstanolone esters Bolazine capronate Drostanolone propionate (dromostanolone propionate) Epitiostanol Mepitiostane Mesterolone Metenolone acetate (methenolone acetate) Metenolone enanthate (methenolone enanthate) Stenbolone acetate 19-Nortestosterone derivatives: Bolandiol dipropionate Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norclostebol Norclostebol acetate Oxabolone cipionate (oxabolone cypionate) Trenbolone acetate Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate) 17α-Alkylated testosterone derivatives: Bolasterone Calusterone Chlorodehydromethyltestosterone (CDMT) Fluoxymesterone Formebolone Metandienone (methandienone, methandrostenolone) Methandriol (methylandrostenediol) Methandriol bisenanthoyl acetate Methandriol dipropionate Methandriol propionate Methyltestosterone Methyltestosterone 3-hexyl ether Oxymesterone Penmesterol Tiomesterone (thiomesterone) 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole Furazabol Mebolazine (dimethazine) Mestanolone Oxandrolone Oxymetholone Stanozolol 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol Mibolerone Norethandrolone Normethandrone (methylestrenolone, normethisterone) Propetandrol (propethandrol) 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone) 17α-Ethynyltestosterone derivatives: Danazol Gestrinone Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]]) Tibolone Progesterone derivatives: Medroxyprogesterone acetate

Progonadotropins

Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;

  | group1 = AR antagonists
  | list1 =

• Steroidal: Abiraterone acetate
• Canrenone
• Chlormadinone acetate
• Cyproterone acetate
• Delmadinone acetate
• Dienogest
• Drospirenone
• Medrogestone
• Megestrol acetate
• Nomegestrol acetate
• Osaterone acetate
• Oxendolone
• Potassium canrenoate
• Spironolactone

• Nonsteroidal: Apalutamide
• Bicalutamide
• Cimetidine
• Darolutamide
• Enzalutamide
• Flutamide
• Ketoconazole
• Nilutamide
• Seviteronel^†
• Topilutamide (fluridil)

  | group2 = Steroidogenesis
inhibitors

| list2 =

5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel† Spironolactone

  | group3 = Antigonadotropins
  | list3 =

• D₂ receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
• Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
• GnRH agonists (e.g., leuprorelin)
• GnRH antagonists (e.g., cetrorelix)
• Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

  | group4 = Others
  | list4 =

• Androstenedione immunogens: Androvax (androstenedione albumin)
• Ovandrotone albumin (Fecundin)

}}

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| list3 =

• ^#WHO-EM
• ^‡Withdrawn from market
• Clinical trials:
  • ^†Phase III
  • ^§Never to phase III

See also

Androgen receptor modulators

Estrogens and antiestrogens

Progestogens and antiprogestogens

List of androgens/anabolic steroids

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