Quinbolone

Quinbolone (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name), sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy.^[2][3][4] It was developed by Parke-Davis^[3] as a viable orally administered AAS with little or no liver toxicity.^[1]

Quinbolone

Clinical data
Trade names	Anabolicum, Anabolvis
Other names	MK-810; Δ1-Testosterone 17β-cyclopent-1-enyl enol ether; 1-Dehydrotestosterone 17β-cyclopent-1-enyl ether; 17β-(1-Cyclopenten-1-yloxy)androsta-1,4-dien-3-one; Androsta-1,4-dien-17β-ol-3-one 17β-(1-cyclopent-1-ene)
Pregnancy category	X
Routes of administration	By mouth[1]
ATC code	A14AA06 (WHO)
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Metabolism	Liver
Excretion	Urine
Identifiers
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
CAS Number	2487-63-0 Y
PubChem CID	10360683
ChemSpider	8536132 Y
UNII	W59598KWLX
KEGG	D05674 Y
CompTox Dashboard (EPA)	DTXSID20179580
Chemical and physical data
Formula	C24H32O2
Molar mass	352.518 g·mol−1
3D model (JSmol)	Interactive image
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
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Pharmacology

Most orally administered anabolic steroids function by having an alkylated 17α-carbon atom, which prevents first-pass metabolism by the liver.^[5] This approach however results in the AAS having hepatotoxicity.^[5] Quinbolone is not 17α-alkylated; instead it has increased oral bioavailability due to its cyclopentenyl ether group.^{[citation needed]} After ingestion, the inactive quinbolone is transformed into boldenone.^[1]

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.^{[1][6][additional citation(s) needed]} 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, AAS.^{[citation needed]} 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.^[5]

Quinbolone, via boldenone, can be transformed into estrogens, and hence may have some estrogenic activity.^[6]

Side effects

See also: Anabolic steroid § Adverse effects

Chemistry

See also: List of androgens/anabolic steroids and List of androgen esters § Ethers of synthetic AAS

Quinbolone, also known as δ¹-testosterone 17β-cyclopent-1-enyl enol ether or as androsta-1,4-dien-17β-ol-3-one 17β-(1-cyclopent-1-ene) enol ether, is a synthetic androstane steroid and a derivative of testosterone.^[2][3] It is the C17β cyclopentyl enol ether of boldenone (δ¹-testosterone).^[2][3] A related AAS is boldenone undecylenate (δ¹-testosterone 17β-undec-10-enoate).^[2][3]

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:^[7]

History

Quinbolone was described as early as 1962.^[7] It was marketed in Italy by Parke-Davis.^[3]