Mesabolone

Mesabolone, also known as 1-testosterone 17β-methoxycyclopentyl ether, is a synthetic anabolic–androgenic steroid (AAS) that was never marketed.[1] It is the 17β-(1-methoxycyclohexane) ether of 1-testosterone (dihydroboldenone).

Mesabolone
Clinical data
Other names1-Testosterone 17β-methoxycyclopentyl ether
Drug classAndrogen; Anabolic steroid; Androgen ether
Identifiers
IUPAC name
  • (5S,8R,9S,10R,13R,14R,17S)-17-(1-methoxycyclohexyl)oxy-10,13-dimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC26H40O3
Molar mass400.603 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@]12CC[C@H]3[C@H]([C@H]1CC[C@@H]2OC4(CCCCC4)OC)CC[C@@H]5[C@@]3(C=CC(=O)C5)C

  • O=C1\C=C/[C@@]5(C)[C@H](C1)CC[C@@H]4[C@@H]5CC[C@@]3(C)[C@H]4CC[C@@H]3OC2(OC)CCCCC2
InChI
  • InChI=1S/C26H40O3/c1-24-15-11-19(27)17-18(24)7-8-20-21-9-10-23(25(21,2)16-12-22(20)24)29-26(28-3)13-5-4-6-14-26/h11,15,18,20-23H,4-10,12-14,16-17H2,1-3H3/t18-,20-,21-,22-,23-,24-,25-/m0/s1 Y
  • Key:AGGYYWICUTUTCC-NMTVEPIMSA-N Y
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Side effects
See also: Anabolic steroid § Adverse effects

Chemistry
See also: List of androgens/anabolic steroids

Synthesis

Syntheses of mesabolone have been published.[2][3]

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 774–. ISBN 978-1-4757-2085-3.
  2. DE 1165021, Bork, Karl-Heinz; Brückner, Klaus & Irmscher, Klaus, "Verfahren zur Herstellung von 16α-Methyl-16β-halogenmethyl-17-ketosteroiden [Process for the preparation of 16α-methyl-16β-halomethyl-17-ketosteroids]", published 1964-03-12, assigned to Merck AG
  3. Vitali R, Gardi R, Falconi G, Ercoli A (October 1966). "New classes of orally active hormonal derivatives. 1. Alkyl androstan-17beta-YL and alkyl 19-norandrostan-17beta-YL mixed acetals". Steroids. 8 (4): 527–36. doi:10.1016/0039-128X(66)90047-X. PMID 5972513.
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