Metenolone enanthate

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Metenolone enanthate
Metenolone enanthate.png
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
Biological half-life IM: 4–5 days[citation needed]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.005.584
Chemical and physical data
Formula C27H42O3
Molar mass 414.621 g/mol
3D model (JSmol)
 NYesY (what is this?)  (verify)

Metenolone enanthate, or methenolone enanthate, sold under the brand names Nibal Injection and Primobolan Depot, is an injected anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group.[1][2][3][4][5] It is a C17β ester of metenolone,[1][2] and acts as a prodrug of metenolone in the body.[5] Whereas metenolone enanthate is the form of metenolone used for intramuscular injection, metenolone acetate is the form used for oral administration.[5]

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.[5] As an AAS, metenolone enanthate is antigonadotropic and can suppress the hypothalamic–pituitary–gonadal axis and produce reversible hypogonadism and infertility.[5][6]

Chemistry[edit]

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]

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.[1][2][3][4] Conversely, metenolone is the INN of metenolone.[1][2][3][4]

Brand names[edit]

Metenolone enanthate is or has been marketed under the brand names Nibal Injection and Primobolan Depot.[1][2][5][4]

Use in sports[edit]

In February 2009, Sports Illustrated reported that Alex Rodriguez tested positive for two AAS, testosterone and metenolone enanthate, while playing for the Texas Rangers in 2003. He claims to have purchased them over the counter, in the Dominican Republic. However, "boli," as he referred to it, is an illegal substance in the Dominican Republic.[7][8] In an interview with ESPN two days after the SI revelations, Rodriguez admitted to using banned substances from 2001 to 2003, citing "an enormous amount of pressure to perform," but said he had not since then used banned performance-enhancing substances.[9][10] He said he did not know the name(s) of the particular substance(s) he was using, and would not specify whether he took them in injectable form.[9]

Metenolone enanthate, which has no approved uses in the United States,[7] is the same AAS with which Barry Bonds allegedly tested positive in 2000 and 2001.[8] A weak AAS on its own, it is generally used in conjunction with other steroids.[11] The drug is generally preferred in injected rather than oral form due to its cost.[11]

References[edit]

  1. ^ a b c d e f g 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. 
  2. ^ a b c d e f g Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN 978-3-88763-075-1. 
  3. ^ 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. 
  4. ^ a b c d https://www.drugs.com/international/metenolone.html
  5. ^ a b c d e f g h William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 633–. ISBN 978-0-9828280-1-4. 
  6. ^ 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. 
  7. ^ a b "Alex Rodriguez tested positive for steroids in 2003". Sports Illustrated. February 2009. Retrieved 2009-02-09.  By Selena Roberts and David Epstein.
  8. ^ a b Schmidt, Michael S. (2009-02-07). "Alex Rodriguez Said to Test Positive in 2003". New York Times. Retrieved 2009-02-09. 
  9. ^ a b Gammons, Peter (2009-02-09). "A-Rod admits, regrets use of PEDs". ESPN. Retrieved 2009-02-09. 
  10. ^ Schmidt, Michael S. (2009-02-09). "Rodriguez Admits to Using Performance-Enhancing Drugs". New York Times. Retrieved 2009-02-09. 
  11. ^ a b Prunty, Brendan (2009-02-07). "What is Primobolan?". Star-Ledger. Retrieved 2009-02-09.