Metenolone acetate

Clinical data
Trade names	Primobolan, Primobolan S, Primonabol, Nibal
Other names	Methenolone acetate; NSC-74226; SH-567; SQ-16496; Methenolone 17β-acetate; 1-Methyl-δ1-4,5α-dihydrotestosterone 17β-acetate; 1-Methyl-δ1-DHT acetate; 1-Methylandrost-1,4-dien-17β-ol-3-one 17β-acetate
Routes of administration	By mouth
Drug class	Androgen;Anabolic steroid;Androgen ester
Identifiers
IUPAC name [(5S,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number	434-05-9
PubChemCID	252372
ChemSpider	221129
UNII	W75590VPKQ
CompTox Dashboard(EPA)	DTXSID40963004
ECHA InfoCard	100.006.453
Chemical and physical data
Formula	C22H32O3
Molar mass	344.495 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C
InChI InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1 Key:PGAUJQOPTMSERF-QWQRBHLCSA-N

Metenolone acetate, ormethenolone acetate, sold under the brand namesPrimobolan andNibal, is anandrogen andanabolic steroid (AAS) medication which is used mainly in the treatment ofanemia due tobone marrow failure.^{[1][2][3][4][5][6]} It is takenby mouth.^[5] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.^[4][5][2] A related drug,metenolone enanthate, is given byinjection into muscle.^[5]

Side effects of metenolone acetate includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.^[5] The drug is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).^[5][7] It has moderateanabolic effects and weakandrogenic effects, as well as noestrogenic effects or risk ofliver damage.^[5][7] Metenolone enanthate is ametenolone ester and aprodrug ofmetenolone in the body.^[5]

Metenolone acetate was introduced for medical use in 1961.^[8][5] In addition to its medical use, metenolone acetate is used toimprove physique and performance.^[5] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.^[5] It remains marketed for medical use only in a few countries, such asJapan andMoldova.^[4][5]

Metenolone acetate, or metenolone 17β-acetate, is asyntheticandrostanesteroid and aderivative of DHT.^[1][2][5] It is the C17βacetateester ofmetenolone, which itself is 1-methyl-δ¹-4,5α-dihydrotestosterone (1-methyl-δ¹-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.^[1][2][5]

• v
• t
• e

Structural properties of major anabolic steroid esters

Anabolic steroid	Structure	Ester				Relative mol. weight	Relative AAS contentb	Durationc
		Position	Moiety	Type	Lengtha
Boldenone undecylenate		C17β	Undecylenic acid	Straight-chain fatty acid	11	1.58	0.63	Long
Drostanolone propionate		C17β	Propanoic acid	Straight-chain fatty acid	3	1.18	0.84	Short
Metenolone acetate		C17β	Ethanoic acid	Straight-chain fatty acid	2	1.14	0.88	Short
Metenolone enanthate		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.37	0.73	Long
Nandrolone decanoate		C17β	Decanoic acid	Straight-chain fatty acid	10	1.56	0.64	Long
Nandrolone phenylpropionate		C17β	Phenylpropanoic acid	Aromatic fatty acid	– (~6–7)	1.48	0.67	Long
Trenbolone acetate		C17β	Ethanoic acid	Straight-chain fatty acid	2	1.16	0.87	Short
Trenbolone enanthated		C17β	Heptanoic acid	Straight-chain fatty acid	7	1.41	0.71	Long
Footnotes:a = Length ofester incarbonatoms forstraight-chain fatty acids or approximate length of ester in carbon atoms foraromatic fatty acids.b = Relative androgen/anabolic steroid content by weight (i.e., relativeandrogenic/anabolicpotency).c =Duration byintramuscular orsubcutaneous injection inoil solution.d = Never marketed.Sources: See individual articles.

Metenolone acetate was first introduced for medical use inWest Germany in 1961 under the brand name Primobolan and in the United States in 1962.^[8][5]

Metenolone acetate is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name, whilemethenolone acetate is itsUSANTooltip United States Adopted Name andBANMTooltip British Approved Name.^{[1][2][3][4][5]}

Metenolone acetate is or has been marketed under a number of brand names including Primobolan, Primobolan S, Primonabol, and Nibal.^{[1][2][3][4][5]}

Metenolone acetate is marketed inJapan andMoldova.^[4][5]

• Acetate esters
• Androgen esters
• Androgens
• Androstanes
• Enones

• Articles with short description
• Short description matches Wikidata
• Short description is different from Wikidata
• ECHA InfoCard ID from Wikidata
• Articles without EBI source
• Chemical pages without DrugBank identifier
• Articles without KEGG source
• Drugs missing an ATC code
• Drugs with no legal status
• Articles containing unverified chemical infoboxes