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 sy ...

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

dehydrogenated In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...

analogue of

testosterone Testosterone is the primary sex hormone and anabolic steroid in males. In humans, testosterone plays a key role in the development of male reproductive tissues such as testes and prostate, as well as promoting secondary sexual characteristi ...

. Boldenone itself has never been marketed; as a

pharmaceutical drug A medication (also called medicament, medicine, pharmaceutical drug, 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 medical field an ...

, 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 i ...

, the undecylenate

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

Side effects

Pharmacology

Pharmacodynamics

Like other AAS, boldenone is an agonist of the androgen receptor (AR). The activity of boldenone is mainly

anabolic Anabolism () is the set of metabolic pathways that construct molecules from smaller units. These reactions require energy, known also as an endergonic process. Anabolism is the building-up aspect of metabolism, whereas catabolism is the breaking ...

, with a low

androgenic An androgen (from Greek ''andr-'', the stem of the word meaning "man") is any natural or synthetic steroid hormone that regulates the development and maintenance of male characteristics in vertebrates by binding to androgen receptors. This incl ...

potency. Boldenone will increase

nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...

retention, protein synthesis, increases appetite and stimulates the release of erythropoietin in the kidneys. Boldenone was synthesized in an attempt to create a long-acting injectable

metandienone Metandienone, also known as methandienone or methandrostenolone and sold under the brand name Dianabol (D-Bol) among others, is an androgen and anabolic steroid (AAS) medication which is still quite often used because of its affordability and eff ...

, for androgen deficiency disorders. Boldenone acts similar to metandienone with fewer adverse androgenic effects. Although commonly compared to

nandrolone Nandrolone, also known as 19-nortestosterone, is an androgen and anabolic steroid (AAS) which is used in the form of esters such as nandrolone decanoate (brand name Deca-Durabolin) and nandrolone phenylpropionate (brand name Durabolin). Nandrolon ...

, boldenone lacks progesterone receptor interaction and associated progestogenic side effects.

Chemistry

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

androstane Androstane is a C19 steroidal hydrocarbon with a gonane core. Androstane can exist as either of two isomers, known as 5α-androstane and 5β-androstane. File:androstane.png, 5α-Androstane File:androstane 5beta.png, 5β-Androstane Pharmacology ...

steroid and a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

. 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 betwee ...

between the C1 and C2 positions. A related compound is

quinbolone Quinbolone (, ), sold under the brand names Anabolicum and Anabolvis, is an androgen and anabolic steroid (AAS) which was previously marketed in Italy. It was developed by Parke-Davis as a viable orally-administered AAS with little or no liver ...

, 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 includ ...

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 s ...

of '' Ilybius fenestratus'', a species of aquatic beetle.

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 pharmaceutical drug, 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) ...

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 or a fixed-dose combination (FDC) is a medicine that includes two or more active ingredients combined in a single dosage form. Terms like "combination drug" or "combination drug product" can be common shorthand for a FDC prod ...

with

methandriol Methandriol (brand names Anabol, Crestabolic, Cytobolin, Diandren, Durabolic, Madiol, Mestenediol, Methabolic, Methydiol, Sterabolic, Stenediol), also known as methylandrostenediol, is an androgen and anabolic steroid (AAS) medication which was ...

under the brand name ''Drive''. In

Ukraine Ukraine ( uk, Україна, Ukraïna, ) is a country in Eastern Europe. It is the second-largest European country after Russia, which it borders to the east and northeast. Ukraine covers approximately . Prior to the ongoing Russian inv ...

, 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 works in a specified professional activity. The term also describes the standards of education and training that prepare members of the profession with the particular knowledge and ski ...

athletes.

References

External links

Equipoise (boldenone undecylenate) - William Llewellyn's Anabolic.org
{{Androgen receptor modulators Secondary alcohols Androgens and anabolic steroids Androstanes Conjugated dienes Drugs in sport Equine medications Enones World Anti-Doping Agency prohibited substances