Boldione, also known as androstadienedione or 1-dehydroandrostenedione, as well as 1,4-androstadiene-3,17-dione, is an important industrial
precursor for various
steroid hormones.
In the
United States the chemical is regulated as a
Schedule III Controlled Substance.
Uses
Androstadienedione is an important industrial-scale
precursor for a wide variety of
steroid hormones within the
estrane and
androstane 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.
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 from
wool 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 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, and
dienedione. 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'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