Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C19H24O2 |
| Molecular Weight | 284.3927 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)C=C[C@]34C
InChI
InChIKey=LUJVUUWNAPIQQI-QAGGRKNESA-N
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
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. Boldione is a direct precursor (prohormone) to the anabolic steroid boldenone (1,4-androstadiene-17beta-ol-3-one). It is advertised as a highly anabolic/androgenic compound promoting muscularity, enhancing strength and overall physical performance, and is available on the Internet and in health stores. Boldione was marketed as a prohormone “dietary supplement” for many years in the mid-2000’s, but it is truly a potent precursor (ie. converts in the body) to the anabolic steroid Boldenone. In 2005 the Anabolic Steroid Control Act of 2005 classified boldenone as a Schedule III controlled illegal steroid.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Unexpected formation of an estrone derivative from androsta-1,4-diene-3,17-dione]. | 2002 Dec |
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| Mixed culture bioconversion of 16-dehydropregnenolone acetate to androsta-1,4-diene-3,17-dione: optimization of parameters. | 2003 Mar-Apr |
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| Biotransformation of (+)-androst-4-ene-3,17-dione. | 2004 Dec |
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| Production of androgens by microbial transformation of progesterone in vitro: a model for androgen production in rivers. | 2004 Nov |
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| [Conversion of androstenedione and androstadienedione by sterol-degrading bacteria]. | 2004 Sep-Oct |
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| The effect of ethambutol on mycobacterial cell wall permeability to hydrophobic compounds. | 2005 |
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| Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. | 2005 Apr 29 |
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| ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results. | 2005 Aug |
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| Mycobacterium sp. mutant strain producing 9alpha-hydroxyandrostenedione from sitosterol. | 2005 Jun |
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| Bioconversion of phytosterols to androstanes by mycobacteria growing on sugar cane mud. | 2005 Mar |
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| Persistence of testosterone and 17beta-estradiol in soils receiving swine manure or municipal biosolids. | 2005 May-Jun |
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| Microbial hydroxylation of pregnenolone derivatives. | 2005 Nov |
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| A very efficient bioconversion of soybean phytosterols mixtures to androstanes by mycobacteria. | 2006 Aug |
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| Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 1. Metabolite profiles of boldenone, boldenone esters and boldione in cattle urine. | 2006 Dec |
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| C19-steroids as androgen receptor modulators: design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists. | 2006 Sep 1 |
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| Effect of anabolics on bovine granulosa-luteal cell primary cultures. | 2007 |
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| Excretion profile of boldenone and its metabolites after oral administration to veal calves. | 2007 Apr 25 |
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| Methyl-beta-cyclodextrin alters growth, activity and cell envelope features of sterol-transforming mycobacteria. | 2007 Jun |
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| An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions. | 2007 Mar 14 |
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| Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata. | 2007 Mar 14 |
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| Development and validation of a liquid chromatography-tandem mass spectrometry method for the separation of conjugated and unconjugated 17alpha- and 17beta-boldenone in urine sample. | 2007 Mar 14 |
|
| The ultimate veal calf reference experiment: hormone residue analysis data obtained by gas and liquid chromatography tandem mass spectrometry. | 2007 Mar 14 |
|
| [Preparation of androsta-1,4-diene-3,17-dione from sterols using Mycobacterium neoaurum VKPM As-1656 strain]. | 2007 May-Jun |
|
| Pathology of the testicle and sex accessory glands following the administration of boldenone and boldione as growth promoters in veal calves. | 2007 Nov |
|
| Studies directed towards a mechanistic evaluation of inactivation of aromatase by the suicide substrates androsta-1,4-diene-3,17-diones and its 6-ene derivatives aromatase inactivation by the 19-substituted derivatives and their enzymic aromatization. | 2007 Nov-Dec |
|
| Boldenone, boldione, and milk replacers in the diet of veal calves: the effects of phytosterol content on the urinary excretion of boldenone metabolites. | 2007 Oct 3 |
|
| Development of a rapid normal-phase LC-positive ion APCI-MS method for simultaneous detection and quantitation of cholesterol, androst-4-ene-3,1 7-dione, and androsta-1,4-diene-3,17-dione. | 2007 Sep |
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| Integrated analytical approach in veal calves administered the anabolic androgenic steroids boldenone and boldione: urine and plasma kinetic profile and changes in plasma protein expression. | 2007 Sep |
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| Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry. | 2008 |
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| Fractionation of free and conjugated steroids for the detection of boldenone metabolites in calf urine with ultra-performance liquid chromatography/tandem mass spectrometry. | 2008 Aug |
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| Enhancement of androstadienedione production from progesterone by biotransformation using the hydroxypropyl-beta-cyclodextrin complexation technique. | 2008 Jan |
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| Boldenone, testosterone and 1,4-androstadiene-3,17-dione determination in faeces from horses, untreated and after administration of androsta-1,4-diene-3,17-dione (boldione). | 2008 Jun |
|
| Naturally occurring progesterone in loblolly pine (Pinus taeda L.): a major steroid precursor of environmental androgens. | 2008 Jun |
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| Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. | 2008 May 2 |
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| Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis. | 2009 Apr 10 |
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| Cholesterol oxidase: physiological functions. | 2009 Dec |
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| Simultaneous determination of 15 steroids in rat blood via gas chromatography-mass spectrometry to evaluate the impact of emasculation on adrenal. | 2009 Dec 15 |
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| A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids. | 2009 Jan 15 |
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| Excretion of endogenous boldione in human urine: influence of phytosterol consumption. | 2009 Oct |
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| Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 2. Direct measurement of 17beta-boldenone sulpho-conjugate in calf urine by liquid chromatography--high resolution and tandem mass spectrometry. | 2009 Oct |
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| Aromatase inactivation by 2-substituted derivatives of the suicide substrate androsta-1,4-diene-3,17-dione. | 2009 Sep |
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| Sitosterol bioconversion with resting cells in liquid polymer based systems. | 2009 Sep |
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| Investigation on possible transformations of cortisol, cortisone and cortisol glucuronide in bovine faecal matter using liquid chromatography-mass spectrometry. | 2010 Apr |
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| Probing the binding pocket of the active site of aromatase with 2-phenylaliphatic androsta-1,4-diene-3,17-dione steroids. | 2010 Apr |
|
| Initial steps in anoxic testosterone degradation by Steroidobacter denitrificans. | 2010 Jul |
|
| Degradation kinetics of testosterone by manure-borne bacteria: influence of temperature, pH, glucose amendments, and dissolved oxygen. | 2010 Jul-Aug |
|
| A new steroid-transforming strain of Mycobacterium neoaurum and cloning of 3-ketosteroid 9alpha-hydroxylase in NwIB-01. | 2010 Nov |
|
| Quantification of testosterone and metabolites released after alkaline treatment in human urine. | 2010 Nov-Dec |
|
| Testosterone metabolism revisited: discovery of new metabolites. | 2010 Oct |
|
| Primary hepatocytes as an useful bioassay to characterize metabolism and bioactivity of illicit steroids in cattle. | 2012 Oct |
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DEA NO. |
4000
Created by
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212-977-2
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SUB194899
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BOLDIONE
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1269083
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DTXSID00862463
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49080
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13472
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C006573
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2166Q8568W
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897-06-3
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40799
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DB07373
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SUBSTANCE RECORD
