4-Chlorodehydromethyltestosterone

4-Chlorodehydromethyltestosterone

Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17S)-4-chloro-17-hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
Clinical data
Pregnancy category	X (US) X (AUS)
Routes of administration	Oral
Legal status
Legal status	Schedule III (US) POM (UK)
Pharmacokinetic data
Bioavailability	100% Oral
Metabolism	Hepatic
Biological half-life	16 hours
Excretion	Kidneys (urine)
Identifiers
CAS Number	2446-23-3
PubChem	CID 98521
ChemSpider	88972
UNII	ZPZ473F40K
Synonyms	4-Chlordehydromethyltestosterone; Dehydrochloromethyltestosterone; 4-Chloromethandienone
Chemical data
Formula	C20H27ClO2
Molar mass	334.89 g/mol
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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4-Chlorodehydromethyltestosterone, sold under the brand name Oral Turinabol, is an anabolic steroid. It is a chlor-substituted version of metandienone (Dianabol). Turinabol 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 and methandrostenolone 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 in 1965. Turinabol was the key steroid administered to approximately 10,000 athletes from East Germany (GDR). The doping program was run by the East German Government from about 1968 until 1989 when the Berlin wall was destroyed. The doping program was known as STASI 14.25. The doping was done in secret and it was only in the 1990s when 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]

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.
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. PMID 9216474.