18-Methyltestosterone

18-Methyltestosterone (18-MT) is an androgen/anabolic steroid (AAS) which was never marketed.[1][2][3] Along with 19-nortestosterone (nandrolone) and 17α-ethynyltestosterone (ethisterone), it is a parent structure of a number of progestogens and AAS. These include the progestogens levonorgestrel (17α-ethynyl-18-methyl-19-nortestosterone) and its derivatives (e.g., desogestrel, gestodene, norgestimate, gestrinone) as well as AAS such as norboletone (17α-ethyl-18-methyl-19-nortestosterone) and tetrahydrogestrinone (THG; δ9,11-17α-ethyl-18-methyl-19-nortestosterone).

Not to be confused with Methyltestosterone.
18-Methyltestosterone
Clinical data
Other names18-MT; 18-Methylandrost-4-en-17β-ol-3-one; 13β-Ethyl-17β-hydroxy-18-norandrost-4-en-3-one
Drug classAndrogen; Anabolic steroid
Identifiers
IUPAC name
  • (8R,9S,10R,13S,14S,17S)-13-ethyl-17-hydroxy-10-methyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC20H30O2
Molar mass302.458 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C
InChI
  • InChI=1S/C20H30O2/c1-3-20-11-9-16-15(17(20)6-7-18(20)22)5-4-13-12-14(21)8-10-19(13,16)2/h12,15-18,22H,3-11H2,1-2H3/t15-,16+,17+,18+,19+,20+/m1/s1
  • Key:VIDBKWVIQCRYHG-HLXURNFRSA-N

See also

References
  1. Baddeley, G. V.; Carpio, H.; Edwards, J. A. (1966). "Steroids. CCLXXXVIII.1The Synthesis of 18-Methylprogesterone and Related Compounds2". The Journal of Organic Chemistry. 31 (4): 1026–1032. doi:10.1021/jo01342a009. ISSN 0022-3263.
  2. Strike, D. P.; Herbst, D.; Smith, Herchel. (1967). "Totally Synthetic Hormones. XVI. The Conversion of Estr-4-en-17β-ol to Testosterone and the Total Synthesis of Some 18-Methylandrostane and 18-Methylpregnane Derivatives". Journal of Medicinal Chemistry. 10 (3): 446–451. doi:10.1021/jm00315a034. ISSN 0022-2623. PMID 22185150.
  3. Rees R, Strike DP, Smith H (September 1967). "Totally synthetic steroid hormones. XVII. Further studies on the synthesis of dl-18-methylandrostane and dl-18-methylpregnane derivatives". J. Med. Chem. 10 (5): 783–9. doi:10.1021/jm00317a006. PMID 6048483.


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