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Metenolone acetate

Metenolone acetate
Metenolone acetate.svg
Clinical data
Trade namesPrimobolan, Primobolan S, Primonabol, Nibal
SynonymsMethenolone acetate; NSC-74226; SH-567; SQ-16496; Methenolone 17β-acetate; 1-Methyl-δ1-4,5α-dihydrotestosterone 17β-acetate; 1-Methyl-δ1-DHT acetate; 1-Methylandrost-1,4-dien-17β-ol-3-one 17β-acetate
Routes of
administration
By mouth
Drug classAndrogen; Anabolic steroid; Androgen ester
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.006.453 Edit this at Wikidata
Chemical and physical data
FormulaC22H32O3
Molar mass344.495 g·mol−1
3D model (JSmol)

Metenolone acetate, or methenolone acetate, sold under the brand names Primobolan and Nibal, 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 taken by mouth.[5] Although it was widely used in the past, the drug has mostly been discontinued and hence is now mostly no longer available.[4][5][2] A related drug, metenolone enanthate, is given by injection into muscle.[5]

Side effects of metenolone acetate 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 prodrug of metenolone in the body.[5]

Metenolone acetate was introduced for medical use in 1961.[8][5] In addition to its medical use, metenolone acetate 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 Japan and Moldova.[4][5]

Side effects

Chemistry

Metenolone acetate, or metenolone 17β-acetate, is a synthetic androstane steroid and a derivative of DHT.[1][2][5] It is the C17β acetate 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]

Structural properties of major anabolic steroid esters

Anabolic steroid Structure Ester Rel. MWb Rel. AASc Durationd
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 enanthatee
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 molecular weight compared to unesterified parent steroid. c = Relative anabolic steroid content by weight (i.e., relative androgenic potency) compared to unesterified parent steroid. d = Duration by intramuscular or subcutaneous injection. e = Never marketed. Sources: See individual articles.

History

Metenolone acetate was first introduced for medical use in West Germany in 1961 under the brand name Primobolan and in the United States in 1962.[8][5]

Society and culture

Generic names

Metenolone acetate is the generic name of the drug and its INN, while methenolone acetate is its USAN and BANM.[1][2][3][4][5]

Brand names

Metenolone acetate is or has been marketed under a number of brand names including Primobolan, Primobolan S, Primonabol, and Nibal.[1][2][3][4][5]

Availability

Metenolone acetate is marketed in Japan and Moldova.[4][5]

References

  1. ^ a b c d e 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 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–661. 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 e f [www.drugs.com]
  5. ^ a b c d e f g h i j k l m n o p q r William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–632. ISBN 978-0-9828280-1-4.
  6. ^ 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.
  7. ^ 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.
  8. ^ a b William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 2109–. ISBN 978-0-8155-1856-3.

External links