Methylhydroxynandrolone

Methylhydroxynandrolone (MOHN, MHN), also known as 4-hydroxy-17α-methyl-19-nortestosterone (HMNT), as well as 4,17β-dihydroxy-17α-methylestr-4-en-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of nandrolone (19-nortestosterone) which was never marketed.[1] It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use.[1][2] The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement".[1] MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.[1]

Methylhydroxynandrolone
Clinical data
Other namesMOHN; MHN; 4-Hydroxy-17α-methyl-19-nortestosterone; HMNT; 4,17β-Dihydroxy-17α-methylestr-4-en-3-one
Routes of
administration		By mouth[1]
Drug classAndrogen; Anabolic steroid
Identifiers
IUPAC name
  • 4,17-dihydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC19H28O3
Molar mass304.430 g·mol−1
3D model (JSmol)
SMILES
  • CC12CCC3C(C1CCC2(C)O)CCC4=C(C(=O)CCC34)O
InChI
  • InChI=1S/C19H28O3/c1-18-9-7-12-11-5-6-16(20)17(21)14(11)4-3-13(12)15(18)8-10-19(18,2)22/h11-13,15,21-22H,3-10H2,1-2H3
  • Key:CLNUZOCYKSHICX-UHFFFAOYSA-N

MOHN is non-aromatizable due to the presence of a hydroxy group at the C4 position, and for this reason, poses no risk of estrogenic side effects like gynecomastia at any dosage, unlike many other AAS.[1] 5α-Reduction is also inhibited by the C4 hydroxy group of MOHN and, because of this, MOHN may have a relatively higher ratio of androgenic to anabolic activity than other nandrolone derivatives (as 5α-reduction, opposite to the case of most other AAS, decreases AAS potency for most nandrolone derivatives).[1] Early assays found that MOHN had approximately 13 times the anabolic activity and 3 times the androgenic activity of methyltestosterone.[1]

MOHN is the 4-hydroxylated derivative of normethandrone (17α-methyl-19-nortestosterone), the 17α-methylated derivative of oxabolone (4-hydroxy-19-nortestosterone), the 4-hydroxylated and 17α-methylated derivative of nandrolone (19-nortestosterone), and the 19-demethylated analogue of oxymesterone (4-hydroxy-17α-methyltestosterone).[1]

See also

References
  1. William Llewellyn (1 November 2008). Anabolics: Anabolic Steroid Reference Guide. William Llewellyn. p. 311. ISBN 978-0-9679304-7-3.
  2. Di Pietro S, Salvadori B (1964). "Sperimentazione Clinica del 4-Idrossi-17-alfa-metil-19-nortestosterone nel Carcinoma Mammario Diffuso" [Clinical Trial with 4-Hydroxy-17α-methyl-19-nortestosterone in Advanced Breast Cancer]. Tumori (in Italian). 50 (6): 445–456. doi:10.1177/030089166405000602. ISSN 0300-8916. PMID 14261594. S2CID 208183701.



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