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
| Molecular Formula | C19H24O2 |
| Molecular Weight | 284.3927 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| Biotransformation of (+)-androst-4-ene-3,17-dione. | 2004 Dec |
|
| Analytical strategies for the detection of non-labelled anabolic androgenic steroids in nutritional supplements. | 2004 Jul |
|
| Confirmatory analysis of 17beta-boldenone, 17alpha-boldenone and androsta-1,4-diene-3,17-dione in bovine urine, faeces, feed and skin swab samples by liquid chromatography-electrospray ionisation tandem mass spectrometry. | 2004 Mar 5 |
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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 |
|
| Screening of anabolic steroids in horse urine by liquid chromatography-tandem mass spectrometry. | 2005 Apr 29 |
|
| ADD, AED, alpha-boldenone and epitestosterone neo formation in calf faeces: preliminary results. | 2005 Aug |
|
| Some unreported by-products from the reaction of 1,4-dien-3-one steroids with 2-(methylammo)benzethiol/BF3. | 2005 Feb |
|
| Mycobacterium sp. mutant strain producing 9alpha-hydroxyandrostenedione from sitosterol. | 2005 Jun |
|
| Bioconversion of phytosterols to androstanes by mycobacteria growing on sugar cane mud. | 2005 Mar |
|
| Persistence of testosterone and 17beta-estradiol in soils receiving swine manure or municipal biosolids. | 2005 May-Jun |
|
| Persistence and pathways of testosterone dissipation in agricultural soil. | 2005 May-Jun |
|
| Androstadienetrione, a boldenone-like component, detected in cattle faeces with GC-MS(n) and LC-MS(n). | 2005 Sep |
|
| Scanning electron microscopy investigations on bis(2-ethylhexyl)phthalate treated Mycobacterium cells. | 2006 Aug |
|
| 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 |
|
| Effect of anabolics on bovine granulosa-luteal cell primary cultures. | 2007 |
|
| Excretion profile of boldenone and its metabolites after oral administration to veal calves. | 2007 Apr 25 |
|
| Methyl-beta-cyclodextrin alters growth, activity and cell envelope features of sterol-transforming mycobacteria. | 2007 Jun |
|
| An in vitro study on metabolism of 17beta-boldenone and boldione using cattle liver and kidney subcellular fractions. | 2007 Mar 14 |
|
| Formation of boldenone and boldenone-analogues by maggots of Lucilia sericata. | 2007 Mar 14 |
|
| 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 |
|
| 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 |
|
| Evaluation of boldenone formation and related steroids transformations in veal faeces by liquid chromatography/tandem mass spectrometry. | 2008 |
|
| 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 |
|
| Enhancement of androstadienedione production from progesterone by biotransformation using the hydroxypropyl-beta-cyclodextrin complexation technique. | 2008 Jan |
|
| 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 |
|
| Comprehensive screening of acidic and neutral drugs in equine plasma by liquid chromatography-tandem mass spectrometry. | 2008 May 2 |
|
| Characterization of 3-ketosteroid 9{alpha}-hydroxylase, a Rieske oxygenase in the cholesterol degradation pathway of Mycobacterium tuberculosis. | 2009 Apr 10 |
|
| Cholesterol oxidase: physiological functions. | 2009 Dec |
|
| Classification of three steroids as schedule III anabolic steroids under the Controlled Substances Act. Final rule. | 2009 Dec 4 |
|
| A new mixed micellar electrokinetic chromatography method for analysis of natural and synthetic anabolic steroids. | 2009 Jan 15 |
|
| 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 |
|
| Aromatase inactivation by 2-substituted derivatives of the suicide substrate androsta-1,4-diene-3,17-dione. | 2009 Sep |
|
| Sitosterol bioconversion with resting cells in liquid polymer based systems. | 2009 Sep |
|
| Investigation on possible transformations of cortisol, cortisone and cortisol glucuronide in bovine faecal matter using liquid chromatography-mass spectrometry. | 2010 Apr |
|
| 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 |
|
| Characterisation of steroids in wooden crates of veal calves by accelerated solvent extraction (ASE) and ultra-high performance liquid chromatography coupled to triple quadrupole mass spectrometry (U-HPLC-QqQ-MS-MS). | 2010 May |
|
| 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 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:58:38 GMT 2023
by
admin
on
Fri Dec 15 17:58:38 GMT 2023
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| Record UNII |
2166Q8568W
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| Record Status |
Validated (UNII)
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| Record Version |
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DEA NO. |
4000
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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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100000181312
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C006573
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DB07373
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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