Quinbolone

Quinbolone

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 category	X
Legal status	Schedule III (US), Schedule IV (CA)
Routes of administration	Oral
Pharmacokinetic data
Bioavailability	?
Metabolism	hepatic
Biological half-life	? days
Excretion	Renal
Identifiers
CAS Number	2487-63-0 N
ATC code	A14AA06 (WHO)
PubChem	CID: 10360683
ChemSpider	8536132 Y
UNII	W59598KWLX Y
KEGG	D05674 Y
Chemical data
Formula	C24H32O2
Molecular mass	352.5156 g/mol
SMILES O=C\1\C=C/[C@]5(/C(=C/1)CC[C@@H]3[C@@H]5CC[C@@]4([C@@H](O/C2=C/CCC2)CC[C@@H]34)C)C
InChI InChI=1S/C24H32O2/c1-23-13-11-17(25)15-16(23)7-8-19-20-9-10-22(26-18-5-3-4-6-18)24(20,2)14-12-21(19)23/h5,11,13,15,19-22H,3-4,6-10,12,14H2,1-2H3/t19-,20-,21-,22-,23-,24-/m0/s1 Y Key:IUVKMZGDUIUOCP-BTNSXGMBSA-N Y
NY (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.

Quinbolone is a derivative of boldenone with 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. After ingestion, the inactive quinbolone becomes boldenone.

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. Because of high doses necessary for androgenic effects, cost and inconvenience meant that quinbolone never proved to be 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

Quinbolone can be prepared from testosterone. Dehydrogenation using DDQ forms boldenone. Reaction with 1,1-dimethoxycyclopentane followed by heating to eliminate methanol gives quinbolone.

Quinbolone synthesis: