Chemistry:Metenolone acetate

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Short description: Chemical compound
Metenolone acetate
Metenolone acetate.svg
Clinical data
Trade namesPrimobolan, Primobolan S, Primonabol, Nibal
Other namesMethenolone 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
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

Pharmacology

v · d · e Androgenic vs. anabolic activity
of androgens/anabolic steroids
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.
v · d · e Parenteral durations of androgens/anabolic steroids
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 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]


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. 1.0 1.1 1.2 1.3 1.4 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. 2.0 2.1 2.2 2.3 2.4 2.5 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. 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. 4.0 4.1 4.2 4.3 4.4 4.5 "List of Androgens and anabolic steroids". drugs.com. https://www.drugs.com/international/metenolone.html. 
  5. 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 William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–632. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT625. 
  6. "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. 7.0 7.1 "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. June 2008. doi:10.1038/bjp.2008.165. PMID 18500378. 
  8. 8.0 8.1 William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 2109–. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA2109-IA118. 

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See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids

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