Boldenone

Boldenone

Clinical data
AHFS/Drugs.com	International Drug Names
Pregnancy category	X (US) X (AUS)
Routes of administration	Intramuscular
ATC code	none
Legal status
Legal status	CA: Schedule IV UK: POM (Prescription only) US: Schedule III
Pharmacokinetic data
Biological half-life	14 days
Identifiers
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
CAS Number	846-48-0 Y
PubChem (CID)	13308
DrugBank	DB01541 Y
ChemSpider	12744 Y
UNII	5H7I2IP58X Y
ChEBI	CHEBI:34584 Y
ChEMBL	CHEMBL2106059 N
Chemical and physical data
Formula	C19H26O2
Molar mass	286.409 g/mol
3D model (Jmol)	Interactive image
Melting point	165 °C (329 °F)
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
InChI 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 Y Key:RSIHSRDYCUFFLA-DYKIIFRCSA-N Y
NY (what is this?)  (verify)

Boldenone (INN, BAN), also known as Δ¹-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-3-one-17β-ol, is a synthetic anabolic-androgenic steroid (AAS) and the 1(2)-dehydrogenated analogue of testosterone. Boldenone itself has never been marketed; as a pharmaceutical drug, it is used as boldenone undecylenate, the undecylenate ester.

Effects and side-effects

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.^[1] Boldenone was synthesized in an attempt to create a long-acting injectable methandrostenolone (Dianabol), for androgen deficiency disorders. Boldenone acts similar to methandrostenolone with fewer adverse androgenic effects. Although commonly compared to nandrolone, boldenone lacks progesterone receptor interaction and all the associated progestogenic side effects.

Use in sports

Baseball

Boldenone is among the substances banned by Major League Baseball, as well as most other major athletic organizations. Los Angeles Angels minor league outfielder Reynaldo Ruiz in September 2010^[2] and Philadelphia Phillies minor league pitcher San Lazaro Solano in January 2011^[3] each received a 50-game suspension for the 2011 season as a result of testing positive for a metabolite of boldenone. Jenrry Mejia, formerly of the New York Mets, was suspended in July 2015 when he tested positive for boldenone and stanozolol, and in February 2016 he again tested positive for boldenone; this marked Mejia's third positive test for a performance-enhancing drug, for which he received the first PED-related lifetime ban in MLB history.^[4] Abraham Almonte was suspended for 80 games before the 2016 season after testing positive for boldenone.^[5]

Mixed martial arts

Stephan Bonnar and Josh Barnett, mixed martial arts (MMA) fighters from the UFC and PRIDE Fighting Championships, have also tested positive for the banned substance.^[6] After the World Extreme Cagefighting show on January 20, 2006 Muay Thai turned MMA fighter Kit Cope also tested positive for boldenone.^[7] Following the Strikeforce card on June 22, 2007 former PRIDE and UFC fighter Phil Baroni tested positive for boldenone, as well as stanozolol.^[8] At a K-1 WGP event in Las Vegas on August 17, 2007 two fighters, Rickard Nordstrand and Zabit Samedov, both tested positive for boldenone.^[9] Alexandre Franca Nogueira tested positive for boldenone in July 2008.^[10]

Antonio Silva tested positive for boldenone after his July 26, 2008 fight against Justin Eilers in the EliteXC promotion. Silva was suspended by the California State Athletic Commission for a year and fined $2500.^[11]

Australian Football League

Justin Charles, a former minor league baseball player with the Florida Marlins, of Richmond FC tested positive for the substance in 1997 and was suspended for 16 matches.^[12]

Major League Soccer

Jon Conway (goal keeper) and Jeff Parke (defender) of the New York Red Bulls both tested positive for the substance in 2008 and were suspended 10 games and fined 10% of their annual income. They are also the first to abuse MLS drug policy.^[13]

Horse racing

Leading horse trainer Gai Waterhouse was fined $10,000 after being found guilty on the 15th of May 2008 of presenting a horse to the races with a prohibited substance in its system. Her horse Perfectly Poised was found to have traces of the banned substance boldenone in its system after finishing second at Canterbury in April 2007.^[14]

See also

• Quinbolone, the 17-cyclopentenyl enol ether of boldenone.

References