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{{Short description|Chemical compound}}
{{Distinguish|1-Testosterone}}
{{Distinguish|1-Testosterone}}
{{Drugbox
{{Drugbox
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| verifiedrevid = 447429808
| verifiedrevid = 447429808
| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-Hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3''H''-cyclopenta[''a'']phenanthren-3-one
| IUPAC_name = (8''R'',9''S'',10''R'',13''S'',14''S'',17''S'')-17-Hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3''H''-cyclopenta[''a'']phenanthren-3-one
| image = Boldenone.png
| image = Boldenone.svg
| width = 225px
| width = 215px
| image2 = Boldenone molecule ball.png
| width2 = 225px


<!--Clinical data-->
<!--Clinical data-->
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| Drugs.com = {{Drugs.com|international|boldenone}}
| Drugs.com = {{Drugs.com|international|boldenone}}
| pregnancy_category = X ([[United States|US]])<br />X ([[Australia|AUS]])
| pregnancy_category = X ([[United States|US]])<br />X ([[Australia|AUS]])
| legal_BR = C5
| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-15 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref>
| legal_CA = Schedule IV
| legal_CA = Schedule IV
| legal_US = Schedule III
| legal_US = Schedule III
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| protein_bound =
| protein_bound =
| metabolism =
| metabolism =
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 14 days (as [[boldenone undecylenate]]){{Citation needed|date=November 2017}}
| elimination_half-life = [[Intramuscular injection|Intramuscular]]: 14 days (as [[boldenone undecylenate]])<ref name="RuizStrain2011">{{cite book| vauthors = Ruiz P, Strain EC |title=Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook|url=https://books.google.com/books?id=w4ZUJAdleTsC&pg=PA358|year=2011|publisher=Lippincott Williams & Wilkins|isbn=978-1-60547-277-5|pages=358–}}</ref>
| excretion =
| excretion =


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<!--Chemical data-->
<!--Chemical data-->
| C=19 | H=26 | O=2
| C=19 | H=26 | O=2
| molecular_weight = 286.409 g/mol
| SMILES = O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]2[C@@H]4CC[C@@]3([C@@H](O)CC[C@@H]23)C)C
| SMILES = O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]2[C@@H]4CC[C@@]3([C@@H](O)CC[C@@H]23)C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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}}
}}


'''Boldenone''', also known as '''Δ<sup>1</sup>-testosterone''', is a [[natural product|naturally occurring]] [[anabolic–androgenic steroid]] (AAS) and the 1(2)-[[dehydrogenated]] [[structural analog|analogue]] of [[testosterone]].<ref name="Elks2014">{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=131–}}</ref><ref name="MortonHall2012">{{cite book|author1=I.K. Morton|author2=Judith M. Hall|title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms|url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}}</ref><ref name="Drugs.com">{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|accessdate=28 April 2017}}</ref><ref name="Llewellyn2011">{{cite book|author=William Llewellyn|title=Anabolics|url=https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483|year=2011|publisher=Molecular Nutrition Llc|isbn=978-0-9828280-1-4|pages=483–}}</ref> Boldenone itself has never been marketed; as a [[pharmaceutical drug]], it is used as [[boldenone undecylenate]], the [[undecylic acid|undecylenate]] [[ester]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />
'''Boldenone''' (developmental code name '''RU-18761'''), is a [[natural product|naturally occurring]] [[anabolic–androgenic steroid]] (AAS) and the 1(2)-[[dehydrogenated]] [[structural analog|analogue]] of [[testosterone]].<ref name="Elks2014">{{cite book| vauthors = Elks J |title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA640|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=640–}}</ref><ref name="IndexNominum2000">{{cite book|title=Index Nominum 2000: International Drug Directory|url=https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA131|year=2000|publisher=Taylor & Francis|isbn=978-3-88763-075-1|pages=131–}}</ref><ref name="MortonHall2012">{{cite book| vauthors = Morton IK, Hall JM |title=Concise Dictionary of Pharmacological Agents: Properties and Synonyms |url=https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA52|date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-94-011-4439-1|pages=52–}}</ref><ref name="Drugs.com">{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|access-date=28 April 2017}}</ref><ref name="Llewellyn2011">{{cite book| vauthors = Llewellyn W |title=Anabolics |url= https://books.google.com/books?id=afKLA-6wW0oC&pg=PT483 |year=2011 |publisher=Molecular Nutrition Llc |isbn=978-0-9828280-1-4 |pages=483–490}}</ref> Boldenone itself has never been marketed; as a [[pharmaceutical drug]], it is used as [[boldenone undecylenate]], the [[undecylic acid|undecylenate]] [[ester]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" />


{{TOC limit|3}}
{{TOC limit|3}}
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===Pharmacodynamics===
===Pharmacodynamics===
Like other AAS, boldenone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> The activity of boldenone is mainly [[anabolic]], with a low [[androgenic]] potency. Boldenone will increase [[nitrogen]] retention, protein synthesis, increases appetite and stimulates the release of [[erythropoietin]] in the kidneys.<ref>Forbes GB (1985) The effect of anabolic steroids on lean body mass the dose response curve. Metab Clin Exp 34(6) 571–573</ref> Boldenone was synthesized in an attempt to create a long-acting injectable [[metandienone]], for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects.{{Medcn|date=September 2015}} Although commonly compared to [[nandrolone]], boldenone lacks [[progesterone receptor]] interaction and associated [[progestogen]]ic side effects.
Like other AAS, boldenone is an [[agonist]] of the [[androgen receptor]] (AR).<ref name="Llewellyn2011" /> The activity of boldenone is mainly [[anabolic]], with a low [[androgenic]] potency. Boldenone will increase [[nitrogen]] retention, protein synthesis, increases appetite and stimulates the release of [[erythropoietin]] in the kidneys.<ref name="Forbes_1985">{{cite journal | vauthors = Forbes GB | title = The effect of anabolic steroids on lean body mass: the dose response curve | journal = Metabolism: Clinical and Experimental | volume = 34 | issue = 6 | pages = 571–3 | date = June 1985 | pmid = 3999979 | doi = 10.1016/0026-0495(85)90196-9 }}</ref>


==Chemistry==
==Chemistry==
{{See also|List of androgens/anabolic steroids}}
{{See also|List of androgens/anabolic steroids}}


Boldenone, also known as Δ<sup>1</sup>-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a [[natural product|naturally occurring]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is specifically testosterone with a [[double bond]] between the C1 and C2 positions.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> A related compound is [[quinbolone]], the 17-[[cyclopentene|cyclopentenyl]] [[enol]] [[ether]] of boldenone.<ref name="Elks2014" /><ref name="IndexNominum2000" />
Boldenone, also known as Δ<sup>1</sup>-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a [[natural product|naturally occurring]] [[androstane]] [[steroid]] and a [[chemical derivative|derivative]] of [[testosterone]].<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> It is specifically testosterone with a [[double bond]] between the C1 and C2 positions.<ref name="Elks2014" /><ref name="IndexNominum2000" /><ref name="Llewellyn2011" /> A related compound is [[quinbolone]], the 17-[[cyclopentene|cyclopentenyl]] [[enol ether]] of boldenone.<ref name="Elks2014" /><ref name="IndexNominum2000" />


===Sources===
===Sources===
Boldenone occurs naturally in the [[scent gland]] of ''[[Ilybius fenestratus]]'', a species of [[beetle]].<ref name="Elks2014" />
Boldenone occurs naturally in the [[scent gland]] of ''[[Ilybius fenestratus]]'', a species of [[aquatic beetle]].<ref name="Elks2014" />


==History==
==History==
[[Ciba Specialty Chemicals|Ciba]] reportedly patented boldenone in 1949.<ref name="Llewellyn2011" /> It subsequently developed several experimental esters of the drug in the 1950s and 1960s.<ref name="Llewellyn2011" /> One of these was boldenone undecylenate, which was introduced for clinical use under the brand name Parenabol and saw some use in the late 1960s and early 1970s.<ref name="Llewellyn2011" /> However, it was discontinued before the end of the 1970s.<ref name="Llewellyn2011" /> Subsequently, boldenone undecylenate was introduced by [[Squibb]] under the brand name Equipose for veterinary use most commonly in horses.<ref name="Llewellyn2011" />
[[Ciba Specialty Chemicals|Ciba]] reportedly patented boldenone in 1949.<ref name="Llewellyn2011" /> It subsequently developed several experimental esters of the drug in the 1950s and 1960s.<ref name="Llewellyn2011" /> One of these was boldenone undecylenate, which was introduced for clinical use under the brand name Parenabol and saw some use in the late 1960s and early 1970s.<ref name="Llewellyn2011" /> However, it was discontinued before the end of the 1970s.<ref name="Llewellyn2011" /> Subsequently, [[boldenone undecylenate]] was introduced by [[Bristol-Myers Squibb|Squibb]] under the brand name Equipose for veterinary use, most commonly in horses.<ref name="Llewellyn2011" />


==Society and culture==
==Society and culture==
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===Brand names===
===Brand names===
Boldenone is marketed as [[veterinary drug]] as boldenone undecylenate (a derivative of boldenone) under the following brand names: Boldebal H, Equipoise, and Sybolin.<ref name="Drugs.com" /> It is marketed as a veterinary [[combination drug]] with [[methandriol]] under the brand name Drive.<ref name="Drugs.com" />
Boldenone is marketed as [[veterinary drug]] as boldenone undecylenate (a derivative of boldenone) under the following brand names: ''Boldebal H'', ''Equipoise'', and ''Sybolin''.<ref name="Drugs.com" /> It is marketed as a veterinary [[combination drug]] with [[methandriol]] under the brand name ''Drive''.<ref name="Drugs.com" />

In [[Ukraine]], it is marketed for human consumption as the injectable steroid ''Boldenol''.<ref name="boldenol">{{cite web | work = Lyka Labs |title=Boldenol 200 (boldenone undecylenate) |url=http://ukroids.club/index.php?main_page=product_info&products_id=5071 |access-date=15 January 2020}}</ref>


===Doping in sports===
===Doping in sports===
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==External links==
==External links==
* [https://anabolic.org/equipoise-boldenone-undecylenate/ Equipoise (boldenone undecylenate) - William Llewellyn's Anabolic.org]
* [https://web.archive.org/web/20190629101049/https://anabolic.org/equipoise-boldenone-undecylenate/ Equipoise (boldenone undecylenate) - William Llewellyn's Anabolic.org]


{{Androgens and antiandrogens}}
{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}
{{Androgen receptor modulators}}


[[Category:Alcohols]]
[[Category:Secondary alcohols]]
[[Category:Androgens and anabolic steroids]]
[[Category:Anabolic–androgenic steroids]]
[[Category:Androstanes]]
[[Category:Androstanes]]
[[Category:Dienes]]
[[Category:Conjugated dienes]]
[[Category:Drugs in sport]]
[[Category:Drugs in sport]]
[[Category:Equine medications]]
[[Category:Equine medications]]
[[Category:Ketones]]
[[Category:Enones]]
[[Category:World Anti-Doping Agency prohibited substances]]

Latest revision as of 12:33, 26 October 2024

Not to be confused with 1-Testosterone.
Boldenone
Clinical data
Other namesΔ1-Testosterone; 1-Dehydrotestosterone; RU-18761; Androsta-1,4-dien-17β-ol-3-one
AHFS/Drugs.comInternational Drug Names
Pregnancy
category
Routes of
administration		Intramuscular injection
Drug classAndrogen; Anabolic steroid
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Elimination half-lifeIntramuscular: 14 days (as boldenone undecylenate)[2]
Identifiers
  • (8R,9S,10R,13S,14S,17S)-17-Hydroxy-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.533 Edit this at Wikidata
Chemical and physical data
FormulaC19H26O2
Molar mass286.415 g·mol−1
3D model (JSmol)
Melting point165 °C (329 °F)
  • O=C\1\C=C/[C@]4(/C(=C/1)CC[C@@H]2[C@@H]4CC[C@@]3([C@@H](O)CC[C@@H]23)C)C
  • InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-17,21H,3-6,8,10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1 checkY
  • Key:RSIHSRDYCUFFLA-DYKIIFRCSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Boldenone (developmental code name RU-18761), is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone.[3][4][5][6][7] Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.[3][4][7]

Side effects

[edit]
See also: Anabolic steroid § Adverse effects

Pharmacology

[edit]

Pharmacodynamics

[edit]

Like other AAS, boldenone is an agonist of the androgen receptor (AR).[7] The activity of boldenone is mainly anabolic, with a low androgenic potency. Boldenone will increase nitrogen retention, protein synthesis, increases appetite and stimulates the release of erythropoietin in the kidneys.[8]

Chemistry

[edit]
See also: List of androgens/anabolic steroids

Boldenone, also known as Δ1-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a naturally occurring androstane steroid and a derivative of testosterone.[3][4][7] It is specifically testosterone with a double bond between the C1 and C2 positions.[3][4][7] A related compound is quinbolone, the 17-cyclopentenyl enol ether of boldenone.[3][4]

Sources

[edit]

Boldenone occurs naturally in the scent gland of Ilybius fenestratus, a species of aquatic beetle.[3]

History

[edit]

Ciba reportedly patented boldenone in 1949.[7] It subsequently developed several experimental esters of the drug in the 1950s and 1960s.[7] One of these was boldenone undecylenate, which was introduced for clinical use under the brand name Parenabol and saw some use in the late 1960s and early 1970s.[7] However, it was discontinued before the end of the 1970s.[7] Subsequently, boldenone undecylenate was introduced by Squibb under the brand name Equipose for veterinary use, most commonly in horses.[7]

Society and culture

[edit]

Generic names

[edit]

Boldenone is the generic name of the drug and its INNTooltip International Nonproprietary Name and BANTooltip British Approved Name.[3][4][5][6]

Brand names

[edit]

Boldenone is marketed as veterinary drug as boldenone undecylenate (a derivative of boldenone) under the following brand names: Boldebal H, Equipoise, and Sybolin.[6] It is marketed as a veterinary combination drug with methandriol under the brand name Drive.[6]

In Ukraine, it is marketed for human consumption as the injectable steroid Boldenol.[9]

Doping in sports

[edit]
See also: List of doping in sport cases § Boldenone undecylenate

There are many known cases of doping in sports with boldenone undecylenate by professional athletes.

References

[edit]
  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-15.
  2. ^ Ruiz P, Strain EC (2011). Lowinson and Ruiz's Substance Abuse: A Comprehensive Textbook. Lippincott Williams & Wilkins. pp. 358–. ISBN 978-1-60547-277-5.
  3. ^ a b c d e f g Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 640–. ISBN 978-1-4757-2085-3.
  4. ^ a b c d e f Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 131–. ISBN 978-3-88763-075-1.
  5. ^ a b Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 52–. ISBN 978-94-011-4439-1.
  6. ^ a b c d "Boldenone international brand names". Drugs.com. Retrieved 28 April 2017.
  7. ^ a b c d e f g h i j Llewellyn W (2011). Anabolics. Molecular Nutrition Llc. pp. 483–490. ISBN 978-0-9828280-1-4.
  8. ^ Forbes GB (June 1985). "The effect of anabolic steroids on lean body mass: the dose response curve". Metabolism: Clinical and Experimental. 34 (6): 571–3. doi:10.1016/0026-0495(85)90196-9. PMID 3999979.
  9. ^ "Boldenol 200 (boldenone undecylenate)". Lyka Labs. Retrieved 15 January 2020.
[edit]
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