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Chemical compound
Quinbolone
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
Routes of administration
By mouth
[1]
ATC code
Legal status
Metabolism
Liver
Excretion
Urine
(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 )
Formula C 24 H 32 O 2
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
Y Key:IUVKMZGDUIUOCP-BTNSXGMBSA-N
Y
(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]
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:
[7]
History
Quinbolone was described as early as 1962.
[7] It was marketed in
Italy by
Parke-Davis .
[3]
References
^
a
b
c
d 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 .
^
a
b
c
d 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 .
^
a
b
c
d
e
f
Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 904–.
ISBN
978-3-88763-075-1 .
^ 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 .
^
a
b
c 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 .
^
a
b 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 .
^
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.
Androgens (incl.
AAS Tooltip anabolic–androgenic steroid )
Antiandrogens
AR Tooltip Androgen receptor
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Agonists
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ER Tooltip Estrogen receptor
Agonists
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3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
3α-Androstanediol
3α,5α-Dihydrolevonorgestrel
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8,9-Dehydroestradiol
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8β-VE2
10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
11β-Chloromethylestradiol
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RU-16117
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Tibolone
Xenoestrogens:
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Lavender oil
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Metalloestrogens (e.g.,
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Phytosteroids (e.g.,
digitoxin (
digitalis ),
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guggulsterone )
Phytosterols (e.g.,
β-sitosterol ,
campesterol ,
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Resorcylic acid lactones (e.g.,
zearalanone ,
α-zearalenol ,
β-zearalenol ,
zearalenone ,
zeranol (α-zearalanol) ,
taleranol (teranol, β-zearalanol) )
Steroid -like (e.g.,
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Stilbenoids (e.g.,
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Mixed (
SERMs Tooltip Selective estrogen receptor modulators ) Antagonists
Coregulator-binding modulators:
ERX-11
GPER Tooltip G protein-coupled estrogen receptor
Agonists Antagonists Unknown