Metenolone enanthate

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Metenolone enanthate
Metenolone enanthate.png
Clinical data
Trade namesNibal Injection, Primobolan Depot
SynonymsMethenolone 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 classAndrogen; Anabolic steroid; Androgen ester
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeIM: 10.5 days[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.005.584 Edit this at Wikidata
Chemical and physical data
FormulaC27H42O3
Molar mass414.621 g/mol 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.[2][3][4][5][6][7] It is given by injection into muscle.[6] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.[5][6][3] A related drug, metenolone acetate, is taken by mouth.[6]

Side effects of metenolone enanthate include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[6] 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).[6][8] It has moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.[6][8] Metenolone enanthate is a metenolone ester and a long-lasting prodrug of metenolone in the body.[6]

Metenolone enanthate was introduced for medical use in 1962.[6] In addition to its medical use, metenolone enanthate is used to improve physique and performance.[6] The drug is a controlled 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 as Spain and Turkey.[5][6]

Medical uses[edit]

Metenolone enanthate has been studied in the treatment of breast cancer.[9][10]

Side effects[edit]

Pharmacology[edit]

Pharmacodynamics[edit]

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.[6] As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility.[6][11]

Pharmacokinetics[edit]

The biological half-life of metenolone enanthate is reported to be about 10.5 days by intramuscular injection.[1]

Parenteral durations of androgens/anabolic steroids

Compound Brand name(s) Type Duration
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.

Chemistry[edit]

Metenolone enanthate, or metenolone 17β-enanthate, is a synthetic androstane steroid and a derivative of DHT.[2][3][6] 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.[2][3][6]

Structural properties of major anabolic steroid esters

Anabolic steroid Structure Ester Relative
mol. weight
Relative
AAS contentb
Durationc
Position Moiety Type Lengtha
Boldenone undecylenate
Boldenone undecylenate.svg
C17β Undecylenic acid Straight-chain fatty acid 11 1.58 0.63 Long
Drostanolone propionate
Drostanolone propionate.svg
C17β Propanoic acid Straight-chain fatty acid 3 1.18 0.84 Short
Metenolone acetate
Metenolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid 2 1.14 0.88 Short
Metenolone enanthate
Metenolone enanthate.png
C17β Heptanoic acid Straight-chain fatty acid 7 1.37 0.73 Long
Nandrolone decanoate
Nandrolone decanoate.svg
C17β Decanoic acid Straight-chain fatty acid 10 1.56 0.64 Long
Nandrolone phenylpropionate
Nandrolone phenylpropionate.svg
C17β Phenylpropanoic acid Aromatic fatty acid – (~6–7) 1.48 0.67 Long
Trenbolone acetate
Trenbolone acetate.svg
C17β Ethanoic acid Straight-chain fatty acid 2 1.16 0.87 Short
Trenbolone enanthated
Trenbolone enanthate.svg
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.

History[edit]

Metenolone enanthate was introduced for medical use in 1962 in the United States under the brand name Nibal Depot.[6] 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.[6]

Society and culture[edit]

Generic names[edit]

Methenolone enanthate is the USAN of metenolone enanthate, and methenolone is the BAN of its active form, metenolone.[2][3][4][5] Conversely, metenolone is the INN of metenolone.[2][3][4][5]

Brand names[edit]

Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.[2][3][6][5]

Availability[edit]

Metenolone enanthate is marketed in Spain and Turkey.[5][6]

Doping in sports[edit]

There are known cases of doping in sports with metenolone enanthate by professional athletes.

References[edit]

  1. ^ a b Pedro Ruiz; Eric C. Strain (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
  2. ^ a b c d e f J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
  3. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. ISBN 978-3-88763-075-1.
  4. ^ a b c I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 178–. ISBN 978-94-011-4439-1.
  5. ^ a b c d e f g https://www.drugs.com/international/metenolone.html
  6. ^ a b c d e f g h i j k l m n o p q r s t William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 633–. ISBN 978-0-9828280-1-4.
  7. ^ J. Larry Jameson; Leslie J. De Groot (25 February 2015). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
  8. ^ a b Kicman AT (2008). "Pharmacology of anabolic steroids". Br. J. Pharmacol. 154 (3): 502–21. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.
  9. ^ Kennedy, B. J.; Yarbro, John W. (1968). "Effect of methenolone enanthate (NSC-64967) in advanced cancer of the breast". Cancer. 21 (2): 197–201. doi:10.1002/1097-0142(196802)21:2<197::AID-CNCR2820210207>3.0.CO;2-R. ISSN 0008-543X.
  10. ^ Notter, G. (1975). "Treatment of Disseminated Carcinoma of the Breast by Metenolone Enanthate". Acta Radiologica: Therapy, Physics, Biology. 14 (6): 545–551. doi:10.3109/02841867509132696. ISSN 0567-8064.
  11. ^ van Breda E, Keizer HA, Kuipers H, Wolffenbuttel BH (Apr 2003). "Androgenic anabolic steroid use and severe hypothalamic-pituitary dysfunction: a case study". Int J Sports Med. 24 (3): 195–196. doi:10.1055/s-2003-39089. PMID 12740738.

External links[edit]