Normethandrone

Normethandrone
Clinical data
Routes of; administration	By mouth
ATC code	G03DC31 (WHO);
Identifiers
	IUPAC name (8R,9S,10R,13S,14S,17S)-17-Hydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;
Synonyms	17α-Methylestr-4-en-17β-ol-3-one; Lutenin; Matronal; Metalutin; Methalutin; Methylestrenolone; Methylnortestosterone; Normetandrone; Normethandrolone; Normethisterone; Normethanedrolone; Orgasteron; RU-598; NSC-10039
CAS Number	514-61-4;
PubChem CID	5284597;
ChemSpider	4447645;
UNII	743F1Z557A;
ChEMBL	CHEMBL269549;
ECHA InfoCard	100.007.440
Chemical and physical data
Formula	C19H28O2
Molar mass	288.42 g/mol
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CCC4=CC(=O)CC[C@H]34 ;
	InChI InChI=1S/C19H28O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16+,17-,18-,19-/m0/s1 ; Key:ZXSWTMLNIIZPET-ZOFHRBRSSA-N ;

Normethandrone (brand names Metalutin, Orgasteron, Lutenin, Matronal), also known as methylestrenolone, normethandrolone, and normethisterone, as well as 17α-methyl-19-nortestosterone or 17α-methylestr-4-en-17β-ol-3-one, is an orally active anabolic-androgenic steroid (AAS) and progestin.^[1]^[2] It has been marketed since 1957.^[3] Normethandrone is the 17α-methylated derivative of nandrolone (19-nortestosterone) and the 17α-methyl variant of norethisterone (17α-ethynyl-19-nortestosterone).

References[edit]

^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 888–. ISBN 978-1-4757-2085-3.
^ Begni-Calvet, D. (1959). "Two properties of methylestrenolone (17-alpha-methyl-19-nortestosterone): Its effectiveness in the treatment of dysmenorrhea, its anabolic action". Gynecologie pratique. 10: 261–272. PMID 13798272.
^ United States. Patent Office (1957). Official Gazette of the United States Patent Office. U.S. Patent Office.

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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 888–. ISBN 978-1-4757-2085-3.

[2] Begni-Calvet, D. (1959). "Two properties of methylestrenolone (17-alpha-methyl-19-nortestosterone): Its effectiveness in the treatment of dysmenorrhea, its anabolic action". Gynecologie pratique. 10: 261–272. PMID 13798272.

[Office1957-3] United States. Patent Office (1957). Official Gazette of the United States Patent Office. U.S. Patent Office.

[1]

[2]

[3]

Normethandrone

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Clinical data

Routes of administration	By mouth
ATC code	G03DC31 (WHO)
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17S)-17-Hydroxy-13,17-dimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms	17α-Methylestr-4-en-17β-ol-3-one; Lutenin; Matronal; Metalutin; Methalutin; Methylestrenolone; Methylnortestosterone; Normetandrone; Normethandrolone; Normethisterone; Normethanedrolone; Orgasteron; RU-598; NSC-10039
CAS Number	514-61-4
PubChem CID	5284597
ChemSpider	4447645
UNII	743F1Z557A
ChEMBL	CHEMBL269549
ECHA InfoCard	100.007.440
Chemical and physical data
Formula	C₁₉H₂₈O₂
Molar mass	288.42 g/mol
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C)O)CCC4=CC(=O)CC[C@H]34
InChI InChI=1S/C19H28O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h11,14-17,21H,3-10H2,1-2H3/t14-,15+,16+,17-,18-,19-/m0/s1 Key:ZXSWTMLNIIZPET-ZOFHRBRSSA-N