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| Clinical data | |
|---|---|
| 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 |
| Routes of administration | Intramuscular injection |
| Drug class | Androgen;Anabolic steroid;Androgen ester |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Eliminationhalf-life | IMTooltip Intramuscular injection: 10.5 days[1] |
| Identifiers | |
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| UNII | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.005.584 |
| Chemical and physical data | |
| Formula | C27H42O3 |
| Molar mass | 414.630 g·mol−1 |
| 3D model (JSmol) | |
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Metenolone enanthate, ormethenolone enanthate, sold under the brand namesPrimobolan Depot andNibal Injection, is anandrogen andanabolic steroid (AAS) medication which is used mainly in the treatment ofanemia due tobone marrow failure.[2][3][4][5][6][7] It is given byinjection into muscle.[6] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly only available on the black market.[5][6][3] A related drug,metenolone acetate, is takenby mouth.[6]
Side effects of metenolone enanthate includesymptoms ofmasculinization likeacne,increased hair growth,voice changes, and increasedsexual desire.[6] The drug is asynthetic androgen and anabolic steroid and hence is anagonist of theandrogen receptor (AR), thebiological target of androgens liketestosterone anddihydrotestosterone (DHT).[6][8] It has moderateanabolic effects and weakandrogenic effects, as well as noestrogenic effects or risk ofliver damage.[6][8] Metenolone enanthate is ametenolone ester and a long-lastingprodrug ofmetenolone in the body.[6]
Metenolone enanthate was introduced for medical use in 1962.[6] In addition to its medical use, metenolone enanthate is used toimprove physique and performance.[6] The drug is acontrolled substance in many countries and so non-medical use is generally illicit.[6] It remains marketed for medical use only in a few countries, such asSpain andTurkey.[5][6]
Metenolone enanthate has been studied in the treatment ofbreast cancer.[9][10]
| Medication | Ratioa |
|---|---|
| Testosterone | ~1:1 |
| Androstanolone (DHT) | ~1:1 |
| Methyltestosterone | ~1:1 |
| Methandriol | ~1:1 |
| Fluoxymesterone | 1:1–1:15 |
| Metandienone | 1:1–1:8 |
| Drostanolone | 1:3–1:4 |
| Metenolone | 1:2–1:3 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:13–1:3 |
| Stanozolol | 1:1–1:3 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:2 |
| 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 notaromatized, and so has no propensity for producingestrogenicside effects likegynecomastia.[6] As an AAS, metenolone enanthate isantigonadotropic and can suppress thehypothalamic–pituitary–gonadal axis and produce reversiblehypogonadism andinfertility.[6][11]
Thebiological half-life of metenolone enanthate is reported to be about 10.5 days byintramuscular injection.[1]
| Medication | Form | Major brand names | Duration |
|---|---|---|---|
| Testosterone | Aqueous suspension | Andronaq, Sterotate, Virosterone | 2–3 days |
| Testosterone propionate | Oil solution | Androteston, Perandren, Testoviron | 3–4 days |
| Testosterone phenylpropionate | Oil solution | Testolent | 8 days |
| Testosterone isobutyrate | Aqueous suspension | Agovirin Depot, Perandren M | 14 days |
| Mixed testosterone estersa | Oil solution | Triolandren | 10–20 days |
| Mixed testosterone estersb | Oil solution | Testosid Depot | 14–20 days |
| Testosterone enanthate | Oil solution | Delatestryl | 14–28 days |
| Testosterone cypionate | Oil solution | Depovirin | 14–28 days |
| Mixed testosterone estersc | Oil solution | Sustanon 250 | 28 days |
| Testosterone undecanoate | Oil solution | Aveed, Nebido | 100 days |
| Testosterone buciclated | Aqueous suspension | 20 Aet-1, CDB-1781e | 90–120 days |
| Nandrolone phenylpropionate | Oil solution | Durabolin | 10 days |
| Nandrolone decanoate | Oil solution | Deca Durabolin | 21–28 days |
| Methandriol | Aqueous suspension | Notandron, Protandren | 8 days |
| Methandriol bisenanthoyl acetate | Oil solution | Notandron Depot | 16 days |
| Metenolone acetate | Oil solution | Primobolan | 3 days |
| Metenolone enanthate | Oil solution | Primobolan Depot | 14 days |
| Note: All are viai.m. injection.Footnotes:a =TP,TV, andTUe.b =TP andTKL.c =TP,TPP,TiCa, andTD.d = Studied but never marketed.e = Developmental code names.Sources: See template. | |||
Metenolone enanthate, or metenolone 17β-enanthate, is asyntheticandrostanesteroid and aderivative of DHT.[2][3][6] It is the C17βenanthate (heptanoate)ester 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.[2][3][6]
| 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 enanthate was introduced for medical use in 1962 in theUnited States under the brand name Nibal Depot.[6] It was soon discontinued in the United States and was marketed instead inEurope in the 1960s and 1970s under the brand name Primobolan Depot.[6]
Methenolone enanthate is theUSANTooltip United States Adopted Name of metenolone enanthate, andmethenolone is theBANTooltip British Approved Name of its active form, metenolone.[2][3][4][5] Conversely,metenolone is theINNTooltip International Nonproprietary Name of metenolone.[2][3][4][5]
Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.[2][3][6][5]
Metenolone enanthate is marketed inSpain andTurkey.[5][6]
There are known cases of doping in sports with metenolone enanthate byprofessionalathletes.