Metandienone

Metandienone
Clinical data

Trade names	Averbol, Dianabol, Danabol, Metanabol, Naposim, Vetanabol
Pregnancy category	US: X (Contraindicated)
Routes of administration	Oral
ATC code	A14AA03 (WHO) D11AE01 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	4.5–6 hours
Excretion	Renal
Identifiers
IUPAC name (8S,9S,10S,13S,14S,17S)-17-Hydroxy-10,13,17-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
Synonyms	Methandienone; Methandrostenolone; Methandrolone; Dehydromethyltestosterone; Methylboldenone; NSC-51180; NSC-42722; 17α-Methyl-δ¹-testosterone; 17α-Methylandrost-1,4-dien-17β-ol-3-one
CAS Number	72-63-9^Y
PubChem CID	6300
ChemSpider	6061^Y
UNII	COZ1R7EOCC
ChEMBL	CHEMBL1418176^N
ECHA InfoCard	100.000.716
Chemical and physical data
Formula	C₂₀H₂₈O₂
Molar mass	300.441 g/mol
3D model (Jmol)	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^Y Key:XWALNWXLMVGSFR-HLXURNFRSA-N^Y
^NY (what is this?)

Metandienone (INN) (brand names Averbol, Dianabol, Danabol, Metanabol, Naposim, Vetanabol), or methandienone (BAN), also known as methandrostenolone, as well as 17α-methyl-δ¹-testosterone or as 17α-methylandrost-1,4-dien-17β-ol-3-one, is an orally active, synthetic anabolic-androgenic steroid (AAS) and a 17α-methylated derivative of testosterone (specifically, the 17α-methylated derivative of boldenone (Δ¹-testosterone)).

Metandienone was originally developed in 1957 by CIBA and marketed in Germany and the United States. As the CIBA product Dianabol, metandienone quickly became became the first widely used anabolic-androgenic steroid among professional and amateur athletes, and remains the most common orally-administered steroid for non-medical use.

It is currently a controlled substance in the U.S. and UK and remains popular among bodybuilders. Metandienone is readily available without a prescription in certain countries such as Mexico (under the brand name Reforvit-b), and is also manufactured in Asia and many Eastern European countries.

Metandienone was first synthesized in 1956 by researchers at the CIBA laboratories in Basel, Switzerland. CIBA filed for a US patent in 1957, and began marketing the compound as Dianabol in 1958.

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