Boldenone (developmental code name RU-18761), is a

naturally occurring A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical ...

anabolic–androgenic steroid (AAS) and the 1(2)- dehydrogenated analogue of

testosterone Testosterone is the primary male sex hormone and androgen in Male, males. In humans, testosterone plays a key role in the development of Male reproductive system, male reproductive tissues such as testicles and prostate, as well as promoting se ...

. Boldenone itself has never been marketed; as a

pharmaceutical drug Medication (also called medicament, medicine, pharmaceutical drug, medicinal product, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacotherapy) is an important part of the ...

, it is used as

boldenone undecylenate Boldenone undecylenate, or boldenone undecenoate, sold under the brand names Equipoise and Parenabol among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, mainly in horses. It was formerly used ...

, the undecylenate

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

Side effects

Pharmacology

Pharmacodynamics

Like other AAS, boldenone is an

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

of the

androgen receptor The androgen receptor (AR), also known as NR3C4 (nuclear receptor subfamily 3, group C, member 4), is a type of nuclear receptor that is activated by binding any of the androgenic hormones, including testosterone and dihydrotestosterone, in th ...

(AR). The activity of boldenone is mainly

anabolic Anabolism () is the set of metabolic pathways that construct macromolecules like DNA or RNA from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catab ...

, with a low androgenic potency. Boldenone will increase

nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...

retention, protein synthesis, increases appetite and stimulates the release of

erythropoietin Erythropoietin (; EPO), also known as erythropoetin, haematopoietin, or haemopoietin, is a glycoprotein cytokine secreted mainly by the kidneys in response to cellular hypoxia; it stimulates red blood cell production ( erythropoiesis) in th ...

in the kidneys.

Chemistry

Boldenone, also known as Δ¹-testosterone, 1-dehydrotestosterone, or androsta-1,4-dien-17β-ol-3-one, is a

androstane

steroid A steroid is an organic compound with four fused compound, fused rings (designated A, B, C, and D) arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes t ...

and a

derivative In mathematics, the derivative is a fundamental tool that quantifies the sensitivity to change of a function's output with respect to its input. The derivative of a function of a single variable at a chosen input value, when it exists, is t ...

. It is specifically testosterone with a

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betw ...

between the C1 and C2 positions. A related compound is quinbolone, the 17- cyclopentenyl

enol ether In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers incl ...

of boldenone.

Sources

Boldenone occurs naturally in the

scent gland Scent gland are exocrine glands found in most mammals. They produce semi-viscous secretions which contain pheromones and other semiochemical compounds. These odor-messengers indicate information such as status, territorial marking, mood, and se ...

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.

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,

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 and .

Brand names

Boldenone is marketed as

veterinary drug An animal drug (also veterinary drug) refers to a drug intended for use in the diagnosis, cure, mitigation, treatment, or prevention of disease in animals. Regulation United States The U.S. Food and Drug Administration (FDA) has the broad mandat ...

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 A combination drug is a combination of two or more pharmaceutical drugs as active ingredients combined into a single dosage form, typically as a ''fixed-dose combination'', with each constituent standardized to specifications of a fixed dose. Fix ...

with methandriol under the brand name ''Drive''. In

Ukraine Ukraine is a country in Eastern Europe. It is the List of European countries by area, second-largest country in Europe after Russia, which Russia–Ukraine border, borders it to the east and northeast. Ukraine also borders Belarus to the nor ...

, it is marketed for human consumption as the injectable steroid ''Boldenol''.

Doping in sports

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

professional A professional is a member of a profession or any person who work (human activity), works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the partic ...

athlete An athlete is most commonly a person who competes in one or more sports involving physical strength, speed, power, or endurance. Sometimes, the word "athlete" is used to refer specifically to sport of athletics competitors, i.e. including track ...

References

External links

Equipoise (boldenone undecylenate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Secondary alcohols Anabolic–androgenic steroids Androstanes Conjugated dienes Drugs in sport Equine medications Enones