Metenolone enanthate

Metenolone enanthate
Clinical data
Trade names Nibal Injection, Primobolan Depot
Synonyms 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
Elimination half-life IM: 10.5 days[1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.005.584 Edit this at Wikidata
Chemical and physical data
Formula C27H42O3
Molar mass 414.621 g/mol
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]

Side effects

Pharmacology

Pharmacodynamics

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][9]

Pharmacokinetics

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

Chemistry

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]

History

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

Generic names

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

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

Availability

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

Doping in sports

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

References

  1. 1 2 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. 1 2 3 4 5 6 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. 1 2 3 4 5 6 7 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. ISBN 978-3-88763-075-1.
  4. 1 2 3 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. 1 2 3 4 5 6 7 https://www.drugs.com/international/metenolone.html
  6. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 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. 1 2 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. ↑ 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.


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