Quinbolone

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Quinbolone
Quinbolone.png
Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17S)-17-(1-Cyclopentenyloxy)-10,13-dimethyl- 6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Clinical data
Pregnancy cat. X
Legal status Schedule III (US), Schedule IV (CA)
Routes Oral
Pharmacokinetic data
Bioavailability ?
Metabolism hepatic
Half-life ? days
Excretion Renal
Identifiers
CAS number 2487-63-0 N
ATC code A14AA06
PubChem CID 10360683
ChemSpider 8536132 YesY
UNII W59598KWLX YesY
KEGG D05674 YesY
Chemical data
Formula C24H32O2 
Mol. mass 352.5156 g/mol
 N (what is this?)  (verify)

Quinbolone (Anabolicum Vister) is an anabolic steroid with weak androgenic effects. It was developed by Parke-Davis in an attempt to create a viable orally-administered anabolic steroid with little or no liver toxicity.

The drug is atypical in that steroid molecules are usually only given officially distinct names when there is a permanent structural difference between the parent molecule and itself. Quinbolone, however, differs from its parent molecule (boldenone) solely by the addition of an easily removed cyclopentenyl ether group.

Most orally administered anabolic steroids function by having an alkylated 17α-carbon atom, which prevents first-pass metabolism by the liver. This approach does, however, give the drug a high hepatotoxicity. Quinbolone is not 17α-alkylated; instead it has increased oral bioavailability due to its cyclopentenyl ether group. This allows the drug to be fully dissolved in an oil base, which is then absorbed into the lymphatic system via the large intestine, from which it travels into the blood. Once there the ester group detaches and the relatively inactive quinbolone becomes boldenone, which then reacts with the androgen receptor of any muscles it comes into contact with.

Quinbolone itself has very few androgenic effects, and most of what it does have are a result of its conversion to boldenone and its metabolites. This, combined with its unusual route of absorption, provides the drug with highly variable results, meaning that large quantities of the drug (100-200 mg per day) must be taken in order to maintain high enough concentrations in the blood for noticeable and consistent effects. The cost and inconvenience of this meant that quinbolone never proved commercially successful, and its clinical applications were fulfilled by alternative, more effective, steroids. Its illicit usage in bodybuilding and athletics likewise proved limited, though drug tests are still used to detect its metabolites as it remains a banned substance for most competitive sports.

Synthesis[edit]

Quinbolone synthesis.png

Reaction of testosterone with DDQ series subtracts hydrogen in ring A, as in the gonane series, to form the cross-conjugated 1,4-diene (). Acetal exchange of this product with the dimethyl acetal () from cyclopentanone gives the mixed acetal (). Heating that product in an inert solvent splits out 1 molar eq. of methanol to give the enol ether quinbolone ().

See also[edit]

  • Boldenone (active metabolite of quinbolone)

References[edit]