Contents

Boldione

Boldione

Clinical data
Other names	1,4-Androstadiene-3,17-dione; 1-Dehydroandrostenedione; androsta-1,4-diene-3,17-dione; ADD
Routes of administration	Oral
Identifiers
IUPAC name (8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione
CAS Number	897-06-3
PubChem CID	13472
ChemSpider	12893
UNII	2166Q8568W
ChEBI	CHEBI:40799
ChEMBL	ChEMBL1078534
CompTox Dashboard (EPA)	DTXSID00862463
ECHA InfoCard	100.011.798
Chemical and physical data
Formula	C19H24O2
Molar mass	284.399 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C\1\C=C/[C@]3(/C(=C/1)CC[C@H]4[C@@H]2CCC(=O)[C@]2(CC[C@H]34)C)C
InChI InChI=1S/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h7,9,11,14-16H,3-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1 Key:LUJVUUWNAPIQQI-QAGGRKNESA-N

Boldione, also known as androstadienedioneor1-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.

Uses[edit]

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

Preparation[edit]

Androstadienedione is obtained in high yield from both plant and animal sterolsbybiotransformation.^[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]

Regulation[edit]

United States[edit]

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]

WADA[edit]

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

References[edit]