Boldenone
{{Short description|Chemical compound}}
{{Distinguish|1-Testosterone}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 447429808
| IUPAC_name = (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
| image = Boldenone.svg
| image_class = skin-invert-image
| width = 215px
| image2 = Boldenone molecule ball.png
| width2 = 225px
| tradename =
| Drugs.com = {{Drugs.com|international|boldenone}}
| pregnancy_category = X (US)
X (AUS)
| legal_BR = C5
| legal_BR_comment = {{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}}
| legal_CA = Schedule IV
| legal_US = Schedule III
| legal_UK = POM
| legal_status =
| routes_of_administration = Intramuscular injection
| class = Androgen; Anabolic steroid
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life = Intramuscular: 14 days (as boldenone undecylenate){{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–}}
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 846-48-0
| ATC_prefix = None
| ATC_suffix =
| PubChem = 13308
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2106059
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01541
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12744
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5H7I2IP58X
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 34584
| synonyms = Δ1-Testosterone; 1-Dehydrotestosterone; RU-18761; Androsta-1,4-dien-17β-ol-3-one
| C=19 | H=26 | O=2
| 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 = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RSIHSRDYCUFFLA-DYKIIFRCSA-N
| melting_point = 165
}}
Boldenone (developmental code name RU-18761), is a naturally occurring anabolic–androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone.{{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–}}{{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–}}{{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–}}{{cite web|title=Boldenone international brand names|url=https://www.drugs.com/international/boldenone.html|publisher=Drugs.com|access-date=28 April 2017}}{{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}} Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.
{{TOC limit|3}}
Side effects
{{See also|Anabolic steroid#Adverse effects}}
Pharmacology
=Pharmacodynamics=
Like other AAS, boldenone is an agonist of the androgen receptor (AR). 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.{{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 }}
Chemistry
{{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. It is specifically testosterone with a double bond between the C1 and C2 positions. A related compound is quinbolone, the 17-cyclopentenyl enol ether of boldenone.
=Sources=
Boldenone occurs naturally in the scent gland of Ilybius fenestratus, a species of aquatic beetle.
In calves not fed boldenone, their urine 17α-boldenone content is strictly related to the phytosterol content of the diet. These naturally occurring amounts present are below doping attention limits.{{cite journal | vauthors = Gallina G, Ferretti G, Merlanti R, Civitareale C, Capolongo F, Draisci R, Montesissa C | title = Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites | journal = Journal of Agricultural and Food Chemistry | volume = 55 | issue = 20 | pages = 8275–83 | date = October 2007 | pmid = 17844992 | doi = 10.1021/jf071097c }}
History
Ciba reportedly patented boldenone in 1949. It subsequently developed several experimental esters of the drug in the 1950s and 1960s. 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. However, it was discontinued before the end of the 1970s. Subsequently, boldenone undecylenate was introduced by Squibb under the brand name Equipose for veterinary use, most commonly in horses.
Society and culture
=Generic names=
Boldenone is the generic name of the drug and its {{abbrlink|INN|International Nonproprietary Name}} and {{abbrlink|BAN|British Approved Name}}.
=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. It is marketed as a veterinary combination drug with methandriol under the brand name Drive.
In Ukraine, it is marketed for human consumption as the injectable steroid 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}}
=Doping in sports=
{{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
{{Reflist|30em}}
External links
- [https://web.archive.org/web/20190629101049/https://anabolic.org/equipoise-boldenone-undecylenate/ Equipoise (boldenone undecylenate) - William Llewellyn's Anabolic.org]
{{Androgens and antiandrogens}}
{{Androgen receptor modulators}}