|Trade names||Nibal Injection, Primobolan Depot|
|Other names||Methenolone enanthate; Metenolone heptanoate; Metenolone 17β-enanthate; NSC-64967; SH-601; SQ-16374; 1-Methyl-4,5α-dihydrotestosterone 17β-heptanoate; 1-Methyl-DHT heptanoate; 1-Methyl-5α-androst-1-en-17β-ol-3-one 17β-heptanoate|
|Drug class||Androgen; Anabolic steroid; Androgen ester|
|Elimination half-life||IM: 10.5 days|
|CompTox Dashboard (EPA)|
|Chemical and physical data|
|Molar mass||414.621 g/mol g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Metenolone enanthate, or methenolone enanthate, sold under the brand names Primobolan Depot and Nibal Injection, is an androgen and anabolic steroid (AAS) medication which is used mainly in the treatment of anemia due to bone marrow failure. It is given by injection into muscle. Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available. A related drug, metenolone acetate, is taken by mouth.
Side effects of metenolone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire. The drug is a synthetic androgen and anabolic steroid and hence is an agonist of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT). It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage. Metenolone enanthate is a metenolone ester and a long-lasting prodrug of metenolone in the body.
Metenolone enanthate was introduced for medical use in 1962. In addition to its medical use, metenolone enanthate is used to improve physique and performance. The drug is a controlled substance in many countries and so non-medical use is generally illicit. It remains marketed for medical use only in a few countries, such as Spain and Turkey.
|Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.|
As a derivative of DHT, metenolone, the active form of metenolone enanthate, is not aromatized, and so has no propensity for producing estrogenic side effects like gynecomastia. As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility.
|Testosterone (aq. susp.)||Andronaq, Sterotate, Virosterone||Androgen||2–3 days|
|Testosterone propionate||Androteston, Perandren, Testoviron||Androgen||3–4 days|
|Testosterone phenylpropionate||Testolent||Androgen||8 days|
|Testosterone isobutyrate (aq. susp.)||Agovirin Depot, Perandren M||Androgen||14 days|
|Mixed testosterone estersa||Triolandren||Androgen||10–20 days|
|Mixed testosterone estersb||Testosid Depot||Androgen||14–20 days|
|Testosterone enanthate||Delatestryl||Androgen||14–20 days|
|Testosterone cypionate||Depovirin||Androgen||14–20 days|
|Mixed testosterone estersc||Sustanon 250||Androgen||28 days|
|Testosterone undecanoate||Aveed, Nebido||Androgen||100 days|
|Testosterone buciclate (aq. susp.)d||20 Aet-1, CDB-1781e||Androgen||90–120 days|
|Nandrolone phenylpropionate||Durabolin||Anabolic||10 days|
|Nandrolone decanoate||Deca Durabolin||Anabolic||21 days|
|Methandriol (aq. susp.)||Notandron, Protandren||Androgen||8 days|
|Methandriol bisenanthoyl acetate||Notandron Depot||Androgen||16 days|
|Metenolone acetate||Primobolan||Anabolic||3 days|
|Metenolone enanthate||Primobolan Depot||Anabolic||14 days|
|Note: All are via i.m. injection of oil solution unless noted otherwise. Footnotes: a = TP, TV, and TUe. b = TP and TKL. c = TP, TPP, TiCa, and TD. d = Studied, but never marketed. e = Developmental code names. Sources: See template.|
Metenolone enanthate, or metenolone 17β-enanthate, is a synthetic androstane steroid and a derivative of DHT. It is the C17β enanthate (heptanoate) ester of metenolone, which itself is 1-methyl-δ1-4,5α-dihydrotestosterone (1-methyl-δ1-DHT) or 1-methyl-5α-androst-1-en-17β-ol-3-one.
|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 of ester in carbon atoms for straight-chain fatty acids or approximate length of ester in carbon atoms for aromatic fatty acids. b = Relative androgen/anabolic steroid content by weight (i.e., relative androgenic/anabolic potency). c = Duration by intramuscular or subcutaneous injection in oil solution. d = Never marketed. Sources: See individual articles.|
Metenolone enanthate was introduced for medical use in 1962 in the United States under the brand name Nibal Depot. It was soon discontinued in the United States and was marketed instead in Europe in the 1960s and 1970s under the brand name Primobolan Depot.