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| Clinical data | |
|---|---|
| Other names | 1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione; androsta-1,4-diene-3,17-dione; ADD |
| Routes of administration | Oral |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.011.798 |
| Chemical and physical data | |
| Formula | C19H24O2 |
| Molar mass | 284.399 g·mol−1 |
| 3D model (JSmol) | |
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Boldione, also known asandrostadienedione or1-dehydroandrostenedione, as well as1,4-androstadiene-3,17-dione, is an important industrialprecursor for varioussteroid hormones.[1] In theUnited States the chemical is regulated as aSchedule III Controlled Substance.
Androstadienedione is an important industrial-scaleprecursor for a wide variety ofsteroid hormones within theestrane andandrostane classifications.[1] For example, boldione was recently used in the synthesis of estrogen.[2][3][4] Additionally, it has been used in the synthesis oftestolactone (via aBaeyer-villiger rearrangement)[5] and ofatamestane.[6] Boldione was used in a synthesis of1-Testosterone.[7]
Androstadienedione is obtained in high yield from both plant and animalsterols bybiotransformation.[1] The chemical is a commonbyproduct derived from other processes (e.g. vegetable oildeodorization and the production oflanolin fromwool processing). The product is produced fromcholesterol by a bacteria in a single step via a simultaneousside-chaincleavage at theC17 position and analcohol oxidation in the C3 position.[8]
The enzyme3-oxosteroid 1-dehydrogenase produces boldione from androstenedione:[9]
In 2004 the United States Congress passed theAnabolic Steroid Control Act of 2005 which placed 36 steroids and over-the-counter prohormones into schedule III of theControlled Substances Act. In this legislation boldenone was classified as a controlled substance and boldione remained legal.[10] 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, anddienedione. 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.[10] Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States.[11]
Boldione is on theWorld Anti-Doping Agency's list of prohibited substances,[12] and is therefore banned from use in most major sports.
