Chemistry:Metenolone enanthate
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| Clinical data | |
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| 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 | |
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| Identifiers | |
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| Chemical and physical data | |
| Formula | C27H42O3 |
| Molar mass | 414.630 g·mol−1 |
| 3D model (JSmol) | |
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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.[1][2][3][4][5][6] It is given by injection into muscle.[5] 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. [4][5][2] A related drug, metenolone acetate, is taken by mouth.[5]
Side effects of metenolone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[5] 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).[5][7] It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.[5][7] Metenolone enanthate is a metenolone ester and a long-lasting prodrug of metenolone in the body.[5]
Metenolone enanthate was introduced for medical use in 1962.[5] In addition to its medical use, metenolone enanthate is used to improve physique and performance.[5] The drug is a controlled 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 as Spain and Turkey.[4][5]
Medical uses
Metenolone enanthate has been studied in the treatment of breast cancer.[8][9]
Side effects
Pharmacology
Pharmacodynamics
| 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 | 1:2–1:30 |
| Oxymetholone | 1:2–1:9 |
| Oxandrolone | 1:3–1:13 |
| Stanozolol | 1:1–1:30 |
| Nandrolone | 1:3–1:16 |
| Ethylestrenol | 1:2–1:19 |
| Norethandrolone | 1:1–1:20 |
| 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.[5] As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility.[5][10]
Pharmacokinetics
The biological half-life of metenolone enanthate is reported to be about 10.5 days by intramuscular injection.[11]
| 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 | 14–20 days |
| Testosterone cypionate | Oil solution | Depovirin | 14–20 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 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 via i.m. injection. 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. | |||
Chemistry
Metenolone enanthate, or metenolone 17β-enanthate, is a synthetic androstane steroid and a derivative of DHT.[1][2][5] 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.[1][2][5]
History
Metenolone enanthate was introduced for medical use in 1962 in the United States under the brand name Nibal Depot.[5] 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.[5]
Society and culture
Generic names
Methenolone enanthate is the USAN of metenolone enanthate, and methenolone is the BAN of its active form, metenolone.[1][2][3][4] Conversely, metenolone is the INN of metenolone.[1][2][3][4]
Brand names
Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.[1][2][5][4]
Availability
Metenolone enanthate is marketed in Spain and Turkey.[4][5]
Doping in sports
There are known cases of doping in sports with metenolone enanthate by professional athletes.
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 784–. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA784.
- ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA660.
- ↑ 3.0 3.1 3.2 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. pp. 178–. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA178.
- ↑ 4.0 4.1 4.2 4.3 4.4 4.5 4.6 "List of Androgens and anabolic steroids". https://www.drugs.com/international/metenolone.html.
- ↑ 5.00 5.01 5.02 5.03 5.04 5.05 5.06 5.07 5.08 5.09 5.10 5.11 5.12 5.13 5.14 5.15 5.16 5.17 5.18 5.19 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 633–. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT625.
- ↑ "Androgen Physiology, Pharmacology, and Abuse". Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. 25 February 2015. pp. 2388–. ISBN 978-0-323-32195-2. https://books.google.com/books?id=xmLeBgAAQBAJ&pg=PA2388.
- ↑ 7.0 7.1 "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. 2008. doi:10.1038/bjp.2008.165. PMID 18500378.
- ↑ "Effect of methenolone enanthate (NSC-64967) in advanced cancer of the breast". Cancer 21 (2): 197–201. February 1968. doi:10.1002/1097-0142(196802)21:2<197::AID-CNCR2820210207>3.0.CO;2-R. PMID 4952912.
- ↑ "Treatment of disseminated carcinoma of the breast by metenolone enanthate". Acta Radiologica 14 (6): 545–551. December 1975. doi:10.3109/02841867509132696. PMID 1224996.
- ↑ "Androgenic anabolic steroid use and severe hypothalamic-pituitary dysfunction: a case study". Int J Sports Med 24 (3): 195–196. Apr 2003. doi:10.1055/s-2003-39089. PMID 12740738.
- ↑ Cite error: Invalid
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