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]

See also

• Chlorodehydromethylandrostenediol
• Chlorodehydromethyltestosterone
• Chloromethylandrostenediol
• Oxymesterone

References

1. Rahnema CD, Crosnoe LE, Kim ED (2015). "Designer steroids - over-the-counter supplements and their androgenic component: review of an increasing problem". Andrology. 3 (2): 150–5. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.
2. Pope HG, Wood RI, Rogol A, Nyberg F, Bowers L, Bhasin S (2014). "Adverse health consequences of performance-enhancing drugs: an Endocrine Society scientific statement". Endocr. Rev. 35 (3): 341–75. doi:10.1210/er.2013-1058. PMC 4026349. PMID 24423981.
3. Rahnema, C. D.; Crosnoe, L. E.; Kim, E. D. (2015). "Designer steroids - over-the-counter supplements and their androgenic component: Review of an increasing problem". Andrology. 3 (2): 150. doi:10.1111/andr.307. PMID 25684733. S2CID 6999218.
4. Lootens, L., Van Eenoo, P., Pozo Mendoza, O. J., Meulemans, P., Leroux-Roels, G., & Delbeke, F. (2010). Application of in vivo urinary steroid detection in uPA+/+-SCID chimeric mice. In 28th Cologne workshop on Dope Analysis (Manfred Donike workshop) (Vol. 18, pp. 52-61). Sportverlag Strauss.
5. "World Anti-Doping Code: International Standard Prohibited List" (PDF). January 2017.