Bolandiol (

INN Inns are generally establishments or buildings where travelers can seek lodging, and usually, food and drink. Inns are typically located in the country or along a highway; before the advent of motorized transportation they also provided accommo ...

, also known as 19-nor-4-androstenediol, estr-4-ene-3β,17β-diol, or 3β-dihydronandrolone) is an

anabolic-androgenic steroid Anabolic steroids, also known more properly as anabolic–androgenic steroids (AAS), are steroidal androgens that include natural androgens like testosterone (medication), testosterone as well as synthetic androgens that are structurally related ...

(AAS) that was never marketed. However, a dipropionate

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 ar ...

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. F ...

bolandiol dipropionate Bolandiol dipropionate (USAN) (brand names Anabiol, Storinal; former developmental code name SC-7525), or bolandiol propionate (JAN), also known as norpropandrolate or 19-nor-4-androstenediol dipropionate, as well as estr-4-ene-3β,17β-diol 3,17 ...

, has been marketed. Bolandiol and its dipropionate ester are unique among AASs in that they reportedly also possesses

estrogen Estrogen or oestrogen is a category of sex hormone responsible for the development and regulation of the female reproductive system and secondary sex characteristics. There are three major endogenous estrogens that have estrogenic hormonal acti ...

ic and

progestogen Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. ...

ic activity. Bolandiol is on the

World Anti-Doping Agency The World Anti-Doping Agency (WADA; french: Agence mondiale antidopage, AMA) is a foundation initiated by the International Olympic Committee based in Canada to promote, coordinate, and monitor the fight against drugs in sports. The agency's key ...

's list of prohibited substances, and is therefore banned from use in most major sports. It is a potential

metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

precursor 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 ...

. However, several clinical studies have concluded that bolandiol does not alter strength, body composition, or exercise performance.

References

{{Progesterone receptor modulators Androgens and anabolic steroids Estranes Estrogens Prodrugs Progestogens World Anti-Doping Agency prohibited substances Cyclohexenols Cyclopentanols Abandoned drugs

See also

References