Quinbolone

Overview

Quinbolone (INN (International Nonproprietary Name), USAN (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. It was developed by Parke-Davis as a viable orally administered AAS with little or no liver toxicity.[1–4] WP

Pharmacology

Pharmacology

Most orally administered anabolic steroids function by having an alkylated 17α-carbon atom, which prevents first-pass metabolism by the liver. This approach however results in the AAS having hepatotoxicity. Quinbolone is not 17α-alkylated; instead it has increased oral bioavailability due to its cyclopentenyl ether group. After ingestion, the inactive quinbolone is transformed into boldenone.[4][5] WP⚠ Wikipedia itself has flagged this text: citation needed.

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, AAS. 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.[4][5][6] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.⚠ Wikipedia itself has flagged this text: citation needed.

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

History

History

Quinbolone was described as early as 1962. It was marketed in Italy by Parke-Davis.[2][7] WP

Chemistry

Formula

C24H32O2 PC

CAS number

2487-63-0 PC

Molar mass (g/mol)

352.5 PC

IUPAC name (computed by PubChem)

(8R,9S,10R,13S,14S,17S)-17-(cyclopenten-1-yloxy)-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one PC

SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2OC4=CCCC4)CCC5=CC(=O)C=C[C@]35C PC

InChIKey

IUVKMZGDUIUOCP-BTNSXGMBSA-N PC

PubChem CID

10360683

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Other Elks J. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014
2. Other Index Nominum 2000: International Drug Directory. 2000
3. Other Morton IK, Hall JM. Concise Dictionary of Pharmacological Agents: Properties and Synonyms. 6 December 2012
4. Journal / agency Galletti F, Gardi R. Metabolism of 1-dehydroandrostanes in man. I. Metabolism of 17 -hydroxyandrosta-1,4-dien-3-one, 17 -cyclopent-1'-enyloxyandrosta-1,4-dien-3-one (quinbolone) and androsta-1,4-diene-3,17-dione (1). Steroids. July 1971. doi:10.1016/s0039-128x(71)80169-1 · PMID 5098537
5. Journal / agency Mullen C, Whalley BJ, Schifano F, Baker JS. Anabolic androgenic steroid abuse in the United Kingdom: An update. British Journal of Pharmacology. May 2020. doi:10.1111/bph.14995 · PMID 31989581 · PMC7174889
6. Other Finkelstein M, Klopper A, Conti C. Research on Steroids: Proceedings of the Fourth Meeting of the International Study Group for Steroid Hormones. 22 October 2013
7. Journal / agency Ercoli A, Gardi R, Vitali R. Steroid-17β-yl acetals and enol ethers. New classes of orally and parenterally active hormonal derivatives. Chemistry & Industry. 1962

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.