Metandienone

Metandienone
Clinical data
Trade names	Dianabol, others
Other names	Methandienone; Methandrostenolone; Methandrolone; Dehydromethyltestosterone; Methylboldenone; Perabol; Ciba-17309-Ba; TMV-17; NSC-51180; NSC-42722; 17α-Methyl-δ1-testosterone; 17β-Hydroxy-17α-methylandrosta-1,4-dien-3-one; 17α-Methylandrost-1,4-dien-17β-ol-3-one
Routes of; administration	By mouth, intramuscular injection (veterinary)
Drug class	Androgen; Anabolic steroid
ATC code	A14AA03 (WHO) D11AE01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C5 (Anabolic steroids); CA: Schedule IV; US: Schedule III;
Pharmacokinetic data
Bioavailability	High
Metabolism	Hepatic
Elimination half-life	3–6 hours
Excretion	Urine
Identifiers
CAS Number	72-63-9 ;
PubChem CID	6300;
DrugBank	DB13586 ;
ChemSpider	6061 ;
UNII	COZ1R7EOCC;
KEGG	D00389;
ChEMBL	ChEMBL1418176 ;
CompTox Dashboard (EPA)	DTXSID2023276 ;
ECHA InfoCard	100.000.716
Chemical and physical data
Formula	C20H28O2
Molar mass	300.442 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]3[C@@H]4CC[C@]2([C@H]3CC[C@@]2(O)C)C)C;
	InChI InChI=1S/C20H28O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1 ; Key:XWALNWXLMVGSFR-HLXURNFRSA-N ;
	S,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[aphenanthren-3-one&page2=Metandienone (verify)]

Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is mostly no longer prescribed. It is also used non-medically for physique- and performance-enhancing purposes. It is often taken by mouth.

Side effects of metandienone include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire, estrogenic effects like fluid retention and breast enlargement, and liver damage. The drug is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT), and has strong anabolic effects and moderate androgenic effects. It also has moderate estrogenic effects.

Metandienone was originally developed in 1955 by CIBA and marketed in Germany and the United States. As the CIBA product Dianabol, metandienone quickly became the first widely used AAS among professional and amateur athletes, and remains the most common orally active AAS for non-medical use. It is currently a controlled substance in the United States and United Kingdom and remains popular among bodybuilders. Metandienone is readily available without a prescription in certain countries such as Mexico, and is also manufactured in some Asian countries.