Normethandrone

Normethandrone
Clinical data
Trade names	Metalutin, others
Other names	Normetandrone; Methylestrenolone; Methyloestrenolone; Methylnortestosterone; Normethyltestosterone; Normethandrolone; Normethisterone; Methylnandrolone; NMT; 17α-Methyl-19-nortestosterone; 17α-Methylestr-4-en-17β-ol-3-one; P-6051; RU-598; NSC-10039
Routes of; administration	By mouth
Drug class	Progestogen; Progestin; Androgen; Anabolic steroid
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;
CAS Number	514-61-4;
PubChem CID	5284597;
ChemSpider	4447645;
UNII	743F1Z557A;
ChEMBL	ChEMBL269549;
CompTox Dashboard (EPA)	DTXSID4023383 ;
ECHA InfoCard	100.007.440
Chemical and physical data
Formula	C19H28O2
Molar mass	288.431 g·mol−1
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, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

Side effects of normethandrone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. It can also cause liver damage. Normethandrone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It is also a synthetic AAS and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has some estrogenic activity as well and no other important hormonal activity.

Normethandrone was introduced for medical use by 1957. It is available only in a few countries, including Brazil, Indonesia, and Venezuela, and is available only in combination with methylestradiol or estradiol valerate.

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