| Systematic (IUPAC) name | |
|---|---|
| (5α,17β)-1-methyl-3-oxoandrost-1-en-17-yl heptanoate | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | Schedule III (US) |
| Pharmacokinetic data | |
| Half-life | 10.5 days |
| Identifiers | |
| CAS number | 303-42-4 |
| ATC code | None |
| PubChem | CID 248271 |
| ChemSpider | 217360 |
| Synonyms | [(5S,8S,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] heptanoate |
| Chemical data | |
| Formula | C27H42O3 |
| Mol. mass | 414.621 g/mol |
| SMILES | eMolecules & PubChem |
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Methenolone enanthate, or metenolone enanthate, is a dihydrotestosterone (DHT) based anabolic steroid. It is an ester derivative of methenolone sold commonly under the brand names Primobolan (tablet form) or Primobolan Depot (injectable). When it interacts with the aromatase enzyme it does not form any estrogens. It is used by people who are very susceptible to estrogenic side effects, having lower estrogenic properties than nandrolone. Methenolone, in form of enanthate and acetate, is available as an injection or as an oral respectively. The injection is naturally regarded as having a higher bioavailability. It is an enanthate ester which is quite long-acting. Because it by-passes hepatic breakdown on the first pass, it also has a higher survival rate. The tablets are in a short-lived acetate form. Methenolone is not 17-alpha-alkylated, but 1-methylated for oral bioavailability. This reduces the stress on the liver, but also the availability. It is considered one of the safer steroids, meaning it has few side effects. Methenolone has no estrogenic side effects, and its effects on cholesterol levels are minimal. In doses of 200 mg per week or less (intramuscular) blood pressure is rarely altered. It is possibly one of the safer anabolic steroids for females due to very low virilization effects in short-term usage. Methenolone is also not overly suppressive of the HPTA axis, although how suppressive is debatable. For this reason, many bodybuilders use it in between steroid cycles during their "off-time" to help maintain their gains and strength. The long term safety of such a practice is possibly dangerous and can lead to permanent suppression of the HPTA.[1]
In February 2009, Sports Illustrated reported that Alex Rodriguez tested positive for two anabolic steroids, testosterone and Primobolan, while playing for the Texas Rangers in 2003. He claims to have purchased them over the counter, in the Dominican Republic. However, "boli" is an illegal substance in the Dominican.[2][3] 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.[4][5] 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.[4]
Primobolan, which has no approved prescriptive use,[2] is the same steroid to which Barry Bonds allegedly tested positive in 2000 and 2001 (though such 'evidence' was dismissed as inadmissible hearsay).[3] A weak steroid on its own, it is generally used in conjunction with other steroids.[6] The drug is generally preferred in injected rather than oral form due to its cost.[6]