18-Methyltestosterone - Misplaced Pages

Chemical compound Not to be confused with Methyltestosterone. Pharmaceutical compound

18-Methyltestosterone
Clinical data

Other names	18-MT; 18-Methylandrost-4-en-17β-ol-3-one; 13β-Ethyl-17β-hydroxy-18-norandrost-4-en-3-one
Drug class	Androgen; 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-dodecahydrocyclopentaphenanthren-3-one
CAS Number	7381-64-8
PubChem CID	54393203
UNII	8MFH3FAP6D
Chemical and physical data
Formula	C₂₀H₃₀O₂
Molar mass	302.458 g·mol
3D model (JSmol)	Interactive image
SMILES CC12CC3(1CC2O)CCC4=CC(=O)CC34C
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

18-Methyltestosterone (18-MT) is an androgen/anabolic steroid (AAS) which was never marketed. 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; δ-17α-ethyl-18-methyl-19-nortestosterone).

References

Baddeley GV, Carpio H, Edwards JA (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.
Strike DP, Herbst D, Smith H (May 1967). "Totally Synthetic Hormones. XVI.(1) The Conversion of Estr-4-en-17-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. PMID 22185150.
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". Journal of Medicinal Chemistry. 10 (5): 783–789. doi:10.1021/jm00317a006. PMID 6048483.

ARTooltip Androgen receptor

Agonists

17α-Alkylated 5α-dihydro-19-nortestosterone derivatives: 5α-Dihydronorethandrolone
5α-Dihydronormethandrone

5α-Dihydro-17α-ethynyl-19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
5α-Dihydronorethisterone

SARMsTooltip Selective androgen receptor modulator

Antagonists

Agonists	Cations (incl. aluminium, calcium, gadolinium, magnesium, strontium, zinc) Dehydroandrosterone Dihydrotestosterone Estradiol L-α-Amino acids (incl. L-arginine, L-lysine, L-ornithine) Osteocalcin SHBGTooltip Sex hormone-binding globulin Testosterone

See also: Receptor/signaling modulators; Androgens and antiandrogens; Estrogen receptor modulators; Progesterone receptor modulators; List of androgens and anabolic steroids

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