Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial

precursor Precursor or Precursors may refer to: *Precursor (religion), a forerunner, predecessor ** The Precursor, John the Baptist Science and technology * Precursor (bird), a hypothesized genus of fossil birds that was composed of fossilized parts of unr ...

for various

steroid hormone A steroid hormone is a steroid that acts as a hormone. Steroid hormones can be grouped into two classes: corticosteroids (typically made in the adrenal cortex, hence ''cortico-'') and sex steroids (typically made in the gonads or placenta). Wi ...

s. In the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...

the chemical is regulated as a

Schedule III Controlled Substance The prohibition of drugs through sumptuary legislation or religious law is a common means of attempting to prevent the recreational use of certain intoxicating substances. While some drugs are illegal to possess, many governments regulate the ...

Uses

Androstadienedione is an important industrial-scale

for a wide variety of

s within the

estrane Estrane is a C18 steroid derivative, with a gonane core. ''Estrenes'' are estrane derivatives that contain a double bond, with an example being nandrolone. ''Estratrienes'' (estrins) are estrane derivatives that contain three double bonds, for i ...

and

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 ...

classifications.

Preparation

Androstadienedione is obtained in high yield from both plant and animal

sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...

s by

biotransformation Biotransformation is the biochemical modification of one chemical compound or a mixture of chemical compounds. Biotransformations can be conducted with whole cells, their lysates, or purified enzymes. Increasingly, biotransformations are effected w ...

. The chemical is a common

byproduct A by-product or byproduct is a secondary product derived from a production process, manufacturing process or chemical reaction; it is not the primary product or service being produced. A by-product can be useful and marketable or it can be consid ...

derived from other processes (e.g. vegetable oil deodorization and the production of

lanolin Lanolin (from Latin 'wool', and 'oil'), also called wool yolk, wool wax, or wool grease, is a wax secreted by the sebaceous glands of wool-bearing animals. Lanolin used by humans comes from domestic sheep breeds that are raised specifically fo ...

from

wool Wool is the textile fibre obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have properties similar to animal wool. As ...

processing). The product is produced in a single step via a simultaneous side-chain cleavage at the C17 position and an

alcohol oxidation Alcohol oxidation is a class of organic reactions in which the alcohol functional group is converted into another functional group (e.g., aldehyde, ketone, carboxylic acid) in which carbon carries a higher oxidation state. Through a variety of mec ...

in the C3 position.

Regulation

United States

In 2004 the United States Congress passed the

Anabolic Steroid Control Act of 2005 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- ...

which placed 36 steroids and over-the-counter prohormones into schedule III of the

Controlled Substances Act The Controlled Substances Act (CSA) is the statute establishing federal government of the United States, federal drug policy of the United States, U.S. drug policy under which the manufacture, importation, possession, use, and distribution of ...

. In this legislation boldenone was classified as a controlled substance and boldione remained legal. In April 2008 the United States Drug Enforcement Administration published an "Initial Notice of Proposed Rulemaking" concerning the scheduling of three anabolic substances: boldione,

desoxymethyltestosterone Desoxymethyltestosterone (DMT), known by the nicknames Madol and Pheraplex, is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-methylated derivative of dihydrotestosterone (DHT) which was never marketed for medical ...

, and

dienedione Dienedione, also known as estra-4,9-diene-3,17-dione, is a synthetic, orally active anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never introduced for medical use. It is thought to be a prohormone of dienolone. The ...

. In 2008, at the time of the proposal, these three substances were listed as ingredients in more than 58 dietary supplements which were available for purchase over the counter. Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States.

WADA

Boldione 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.

References

{{Androgen receptor modulators Androgens and anabolic steroids Androstanes Diketones World Anti-Doping Agency prohibited substances