Boldenone

Not to be confused with 1-Testosterone.

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]

Boldenone

Clinical data
Other names	Δ1-Testosterone; 1-Dehydrotestosterone; RU-18761; Androsta-1,4-dien-17β-ol-3-one
AHFS/Drugs.com	International Drug Names
Pregnancy category	X (US) X (AUS)
Routes of administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid
ATC code	None
Legal status
Legal status	BR: Class C5 (Anabolic steroids)[1] CA: Schedule IV UK: POM (Prescription only) US: Schedule III
Pharmacokinetic data
Elimination half-life	Intramuscular: 14 days (as boldenone undecylenate)[2]
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
ChEBI	CHEBI:34584 Y
ChEMBL	ChEMBL2106059 N
CompTox Dashboard (EPA)	DTXSID20894201
ECHA InfoCard	100.011.533
Chemical and physical data
Formula	C19H26O2
Molar mass	286.415 g·mol−1
3D model (JSmol)	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)

Side effects

See also: Anabolic steroid § Adverse effects

Pharmacology

Pharmacodynamics

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

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

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

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.^[9]

History

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

Generic names

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

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.^[10]

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.