Methylclostebol

Methylclostebol, also known as 4-chloro-17α-methyltestosterone or as 4-chloro-17α-methylandrost-4-en-17β-ol-3-one, is a synthetic, orally active anabolic-androgenic steroid (AAS) and designer steroid that has been sold on the Internet as a "dietary supplement",^[1][2] but it has never been studied for medical use.^[3] It is the 17α-alkylated variant of clostebol (4-chlorotestosterone).^[4]

Methylclostebol

Clinical data
Other names	Chloromethyltestosterone; CMT; 4-Chloro-17α-methyltestosterone; 4-Chloro-17α-methylandrost-4-en-17β-ol-3-one
Routes of administration	Oral
Legal status
Legal status	US: Schedule III
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17S)-4-Chloro-17-hydroxy-10,13,17-trimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number	5785-58-0
PubChem CID	227107
ChemSpider	197559
UNII	0956Z23Q9N
ChEBI	CHEBI:79860
Chemical and physical data
Formula	C20H29ClO2
Molar mass	336.90 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CCC(=O)C(=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C)O)C)Cl
InChI InChI=1S/C20H29ClO2/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/h12-14,23H,4-11H2,1-3H3/t12-,13+,14+,18-,19+,20+/m1/s1 Key:SOMOGWLYTLQJGT-XMUHMHRVSA-N

Rahnema, Crosnoe, and Kim (2015) reported that German athletes used methylclostebol as a performance enhancing drug in the 1960s and 1970s, but this has not been substantiated.^[3] The compound is listed as a banned anabolic agent by the World Anti-Doping Agency.^[5]