Metenolone

Not to be confused with metandienone (methandrostenolone).
Metenolone
Clinical data
Trade namesPrimobolan, Nibal (as metenolone acetate); Primobolan Depot, Nibal Injection (as metenolone enanthate)
Other namesMethenolone; Methylandrostenolone; 1-Methyl-δ1-4,5α-dihydrotestosterone; 1-Methyl-δ1-DHT; 1-Methyl-5α-androst-1-en-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth (as metenolone acetate), intramuscular injection (as metenolone enanthate)
Drug classAndrogen; Anabolic steroid
ATC code
Legal status
Legal status
Identifiers
  • (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-1,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.005.285 Edit this at Wikidata
Chemical and physical data
FormulaC20H30O2
Molar mass302.458 g·mol−1
3D model (JSmol)
  • O=C2\C=C(\C)[C@@]3([C@H]1CC[C@@]4([C@@H](O)CC[C@H]4[C@@H]1CC[C@H]3C2)C)C
  • InChI=1S/C20H30O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h10,13,15-18,22H,4-9,11H2,1-3H3/t13-,15-,16-,17-,18-,19-,20-/m0/s1 checkY
  • Key:ANJQEDFWRSLVBR-VHUDCFPWSA-N checkY

Metenolone, or methenolone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as metenolone acetate (brand name Primobolan, Nibal) and metenolone enanthate (brand name Primobolan Depot, Nibal Injection).[2][3][4][5][6] Metenolone esters are used mainly in the treatment of anemia due to bone marrow failure.[7] Metenolone acetate is taken by mouth, while metenolone enanthate is given by injection into muscle.[6]

Side effects of metenolone esters include symptoms of masculinization like acne, increased hair growth, voice changes, and increased sexual desire.[6] Metenolone esters are synthetic androgens and anabolic steroids and hence are agonists of the androgen receptor (AR), the biological target of androgens like testosterone and dihydrotestosterone (DHT).[6][8] They have moderate anabolic effects and weak androgenic effects, as well as no estrogenic effects or risk of liver damage.[6][8] Metenolone esters are androgen esters and prodrugs of metenolone in the body.[6]

Metenolone esters were introduced for medical use in the early 1960s.[6] In addition to their medical use, metenolone esters are used to improve physique and performance.[6] The drugs are controlled substances in many countries and so non-medical use is generally illicit.[6] They have mostly been discontinued for medical use and have limited availability.[5][6]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 784–. ISBN 978-1-4757-2085-3.
  3. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 659–660. ISBN 978-3-88763-075-1.
  4. ^ Morton IK, Hall JM (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 "List of Androgens and anabolic steroids". Drugs.com.
  6. ^ a b c d e f g h i j William Llewellyn (2011). Anabolics. Molecular Nutrition Llc. pp. 625–, 633–. ISBN 978-0-9828280-1-4.
  7. ^ Handelsman DJ (25 February 2015). "Androgen Physiology, Pharmacology, and Abuse". In Jameson JL, De Groot LJ (eds.). Endocrinology: Adult and Pediatric E-Book. Elsevier Health Sciences. pp. 2388–. ISBN 978-0-323-32195-2.
  8. ^ a b Kicman AT (June 2008). "Pharmacology of anabolic steroids". British Journal of Pharmacology. 154 (3): 502–521. doi:10.1038/bjp.2008.165. PMC 2439524. PMID 18500378.