Quinbolone

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Quinbolone
Quinbolone.png
Quinbolone molecule ball.png
Clinical data
Trade names Anabolicum, 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
Metabolism Liver
Excretion Urine
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
Formula C24H32O2
Molar mass 352.518 g·mol−1
3D model (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 Yes check.svgY
  • Key:IUVKMZGDUIUOCP-BTNSXGMBSA-N Yes check.svgY
   (verify)

Quinbolone (INN Tooltip International Nonproprietary Name, USAN Tooltip 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]

Contents

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

Chemistry

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: Quinbolone synthesis.png
Quinbolone synthesis:

History

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

Related Research Articles

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<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

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<span class="mw-page-title-main">Metandienone</span> Androgen and anabolic steroid

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<span class="mw-page-title-main">Boldenone</span> Chemical compound

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<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

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<span class="mw-page-title-main">Mesterolone</span> Chemical compound

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<span class="mw-page-title-main">Ethisterone</span> Chemical compound

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<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

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<span class="mw-page-title-main">Methandriol</span> Chemical compound

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<span class="mw-page-title-main">Enestebol</span> Chemical compound

Enestebol, also known as 4-hydroxy-17α-methyl-δ1-testosterone, as well as 4,17β-dihydroxy-17α-methylandrosta-1,4-dien-3-one, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated derivative of testosterone which was never marketed. It is closely related to oxymesterone (4-hydroxy-17α-methyltestosterone), as well as to chlorodehydromethyltestosterone (4-chloro-17α-methyl-δ1-testosterone), methylclostebol (4-chloro-17α-methyltestosterone), and metandienone (17α-methyl-δ1-testosterone).

<span class="mw-page-title-main">Normethandrone</span> Chemical compound

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

<span class="mw-page-title-main">Quingestanol acetate</span> Chemical compound

Quingestanol acetate, sold under the brand names Demovis and Pilomin among others, is a progestin medication which was used in birth control pills but is no longer marketed. It is taken by mouth.

<span class="mw-page-title-main">Methylepitiostanol</span> Chemical compound

Methylepitiostanol, known by the nicknames Epistane, Hemapolin, Havoc, and Epi Plex, is a synthetic and orally active anabolic–androgenic steroid (AAS) of the dihydrotestosterone (DHT) group which was first described in the literature in 1974 but was never marketed for medical use. It is the 17α-methylated derivative of epitiostanol, an AAS and antiestrogen which was formerly used in the treatment of breast cancer in Japan. Similarly to mepitiostane, methylepitiostanol is an orally active variant of epitiostanol. Due to its C17α methyl group, the drug is considered to have a high potential for hepatotoxicity.

<span class="mw-page-title-main">Boldenone undecylenate</span> Chemical compound

Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used in humans as well. It is given by injection into muscle.

<span class="mw-page-title-main">11β-Methyl-19-nortestosterone</span> Chemical compound

11β-Methyl-19-nortestosterone (11β-MNT) is a synthetic and orally active anabolic–androgenic steroid (AAS) and a derivative of nandrolone (19-nortestosterone) which was developed by the Contraceptive Development Branch (CDB) of the National Institute of Child Health and Human Development (NICHD) and has not been marketed at this time.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. 1 2 3 4 Galletti F, Gardi R (July 1971). "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. 18 (1): 39–50. doi:10.1016/s0039-128x(71)80169-1. PMID   5098537.
  2. 1 2 3 4 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1056–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 904–. ISBN   978-3-88763-075-1.
  4. ↑ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 243–. ISBN   978-94-011-4439-1.
  5. 1 2 3 Mullen C, Whalley BJ, Schifano F, Baker JS (May 2020). "Anabolic androgenic steroid abuse in the United Kingdom: An update". British Journal of Pharmacology. 177 (10): 2180–2198. doi:10.1111/bph.14995. PMC   7174889 . PMID   31989581.
  6. 1 2 Finkelstein M, Klopper A, Conti C (22 October 2013). Research on Steroids: Proceedings of the Fourth Meeting of the International Study Group for Steroid Hormones. Elsevier Science. pp. 121–. ISBN   978-1-4831-5403-9.
  7. 1 2 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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