Methylhydroxynandrolone

{{Short description|Chemical compound}}

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| 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

| image = Methylhydroxynandrolone.svg

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| routes_of_administration = By mouth

| class = Androgen; Anabolic steroid

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| CAS_number = 2747-16-2

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| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AL9HUA7C4C

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| PubChem = 351707

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| ChemSpiderID = 312271

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| synonyms = MOHN; MHN; 4-Hydroxy-17α-methyl-19-nortestosterone; HMNT; 4,17β-Dihydroxy-17α-methylestr-4-en-3-one

| C=19 | H=28 | O=3

| SMILES = CC12CCC3C(C1CCC2(C)O)CCC4=C(C(=O)CCC34)O

| StdInChI_Ref =

| StdInChI = 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

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| StdInChIKey = CLNUZOCYKSHICX-UHFFFAOYSA-N

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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.{{cite book|author=William Llewellyn|title=Anabolics: Anabolic Steroid Reference Guide|url=https://books.google.com/books?id=3-FAQgAACAAJ|date=1 November 2008|publisher=William Llewellyn|isbn=978-0-9679304-7-3|page=311}} It was first described in 1964 and was studied in the treatment of breast cancer, but was not introduced for clinical use.{{cite journal | vauthors = Di Pietro S, Salvadori B | title = Sperimentazione Clinica del 4-Idrossi-17-alfa-metil-19-nortestosterone nel Carcinoma Mammario Diffuso | trans-title = Clinical Trial with 4-Hydroxy-17α-methyl-19-nortestosterone in Advanced Breast Cancer | language = it | journal = Tumori | volume = 50 | issue = 6 | pages = 445–456 | date = 1964 | issn = 0300-8916 | pmid = 14261594 | doi = 10.1177/030089166405000602 | s2cid = 208183701 }} The drug re-emerged in 2004 when it started being sold on the Internet as a "dietary supplement". MOHN joined other AAS as a controlled substance in the United States on 20 January 2005.

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. 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). Early assays found that MOHN had approximately 13 times the anabolic activity and 3 times the androgenic activity of methyltestosterone.

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).