Quinbolone

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Quinbolone
Clinical data
Trade namesAnabolicum, Anabolvis
Other namesMK-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
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
ExcretionUrine
Identifiers
  • (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
JSmol)
  • 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=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 checkY
  • Key:IUVKMZGDUIUOCP-BTNSXGMBSA-N checkY
  (verify)

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]

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

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

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

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]

References

  1. ^
    PMID 5098537
    .
  2. ^
    ISBN 978-1-4757-2085-3
    .
  3. ^
    ISBN 978-3-88763-075-1
    .
  4. ISBN 978-94-011-4439-1
    .
  5. ^
    PMID 31989581
    .
  6. ^
    ISBN 978-1-4831-5403-9
    .
  7. ^ a b Ercoli A, Gardi R, Vitali R (1962). "Steroid-17β-yl acetals and enol ethers. New classes of orally and parenterally active hormonal derivatives". Chemistry & Industry. 28: 1284–1285.
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