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.[1] In the United States the chemical is regulated as a Schedule III Controlled Substance.

Boldione
Boldione.png
Clinical data
Other names1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione
Routes of
administration
Oral
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.011.798 Edit this at Wikidata
Chemical and physical data
FormulaC19H24O2
Molar mass284.39 g/mol g·mol−1
3D model (JSmol)

UsesEdit

Androstadienedione is an important industrial-scale precursor for a wide variety of steroid hormones within the estrane and androstane classifications.[1]

PreparationEdit

Androstadienedione is obtained in high yield from both plant and animal sterols by biotransformation.[1] The chemical is a common byproduct 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 in the C3 position.[2]

RegulationEdit

United StatesEdit

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. In this legislation boldenone was classified as a controlled substance and boldione remained legal.[3] 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.[3] Effective January 4, 2010 these three chemicals, including boldione, were classified as Schedule III Controlled Substances and became illegal in the United States.[4]

WADAEdit

Boldione is on the World Anti-Doping Agency's list of prohibited substances,[5] and is therefore banned from use in most major sports.

ReferencesEdit

  1. ^ a b c Sandow, Jürgen; Scheiffele, Ekkehard; Haring, Michael; Neef, Günter; Prezewowsky, Klaus; Stache, Ulrich (2000). "Hormones". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a13_089. ISBN 3527306730.
  2. ^ Hesselink, Paul G.M.; Vliet, Steven van; Vries, Harrie de; Witholt, Bernard (1989). "Optimization of steroid side chain cleavage by Mycobacterium sp. in the presence of cyclodextrins". Enzyme and Microbial Technology. 11 (7): 398–404. doi:10.1016/0141-0229(89)90133-6.
  3. ^ a b "Archived copy" (PDF). Archived from the original (PDF) on 2010-10-17. Retrieved 2010-10-20.CS1 maint: archived copy as title (link)
  4. ^ http://www.deadiversion.usdoj.gov/fed_regs/rules/2009/fr1204.htm
  5. ^ "The World Anti-Doping Code: The 2020 Prohibited List" (PDF). World Anti-Doping Agency. Retrieved 2019-12-28.