Metenolone acetate
Chemical compound
Metenolone acetate Trade names Primobolan, Primobolan S, Primonabol, Nibal Other names Methenolone 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 class Androgen ; Anabolic steroid ; Androgen ester
[(5S ,8R ,9S ,10S ,13S ,14S ,17S )-1,10,13-Trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a ]phenanthren-17-yl] acetate
CAS Number PubChem CID ChemSpider UNII CompTox Dashboard (EPA ) ECHA InfoCard 100.006.453 Formula C 22 H 32 O 3 Molar mass 344.495 g·mol−1 3D model (JSmol )
CC1=CC(=O)C[C@H]2[C@]1([C@H]3CC[C@]4([C@H]([C@@H]3CC2)CC[C@@H]4OC(=O)C)C)C
InChI=1S/C22H32O3/c1-13-11-16(24)12-15-5-6-17-18-7-8-20(25-14(2)23)21(18,3)10-9-19(17)22(13,15)4/h11,15,17-20H,5-10,12H2,1-4H3/t15-,17-,18-,19-,20-,21-,22-/m0/s1
Key:PGAUJQOPTMSERF-QWQRBHLCSA-N
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
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 esters a
Oil solution
Triolandren
10–20 days
Mixed testosterone esters b
Oil solution
Testosid Depot
14–20 days
Testosterone enanthate
Oil solution
Delatestryl
14–28 days
Testosterone cypionate
Oil solution
Depovirin
14–28 days
Mixed testosterone esters c
Oil solution
Sustanon 250
28 days
Testosterone undecanoate
Oil solution
Aveed, Nebido
100 days
Testosterone buciclate d
Aqueous suspension
20 Aet-1, CDB-1781e
90–120 days
Nandrolone phenylpropionate
Oil solution
Durabolin
10 days
Nandrolone decanoate
Oil solution
Deca Durabolin
21–28 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 Tooltip International Nonproprietary Name , while methenolone acetate is its USAN Tooltip United States Adopted Name and BANM Tooltip British Approved Name .[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
Androgens (incl. AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor antagonists Steroidogenesis inhibitors
Antigonadotropins
D2 receptor antagonists (prolactin releasers ) (e.g., domperidone , metoclopramide , risperidone , haloperidol , chlorpromazine , sulpiride )
Estrogens (e.g., bifluranol , diethylstilbestrol , estradiol , estradiol esters , ethinylestradiol , ethinylestradiol sulfonate , paroxypropione )
GnRH agonists (e.g., leuprorelin )
GnRH antagonists (e.g., cetrorelix )
Progestogens (incl., chlormadinone acetate , cyproterone acetate , hydroxyprogesterone caproate , gestonorone caproate , medroxyprogesterone acetate , megestrol acetate )
Others
AR Tooltip Androgen receptor
Agonists SARMs Tooltip Selective androgen receptor modulator Antagonists
GPRC6A