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MSACL 2013 Oral Fluid Steroids

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MSACL 2013 Oral Fluid Steroids Testing Androgenic Anabolic Steroids in Oral Fluid using Turbulent Flow Orbitrap Mass Spectrometry Erica A. Guice, Matt Pentis, and Brad Holden Western Slope Laboratory, LLC Erica A. Guice is the Director of Research and Development at Western Slope Laboratory. Brad Holden and Matt Pentis were employed as Junior Analytical Chemists at Western Slope Laboratory for the course of this research. Funding for this research was provided by Western Slope Laboratory. Thermo Fisher Scientific supported this research by providing instrumentation. Outline • Background in AAS testing OF • Details of Method • Details of Current Study • Future Plans Developments with Western Slope Laboratory and beyond…. BACKGROUND IN ANABOLIC ANDROGENIC STEROID TESTING IN ORAL FLUID Foundation in Oral Fluid • Western Slope Laboratory was founded on oral fluid technologies and have continued down that path – Test for hundreds of analytes in oral fluid – Same catalogue as urine analytes – Low limits of detection and quantification Oral Fluid-Matrix of the Future? • Most toxicology laboratories now offer some testing with the oral fluid matrix • BUT, there are not any commercial laboratories that offer oral fluid steroid testing….Western Slope Laboratory sought to develop the method DETAILS OF METHODOLOGY Goal of testing for steroids: o For forensics: low limits of detection for as many compounds and their analogues o For post mortem: large dynamic range for as many compounds and their analogues o For clinical: low limits of detection for a specific group of compounds o For doping: large dynamic range for a specific group of compounds The Analytes • Androgenic anabolic steroids are hormones that mimic testosterone – They are lipids, but much different structure than the classical lipid – they are non-polar ∴ Need solvent based sample preparation probably SPE and high organic in mobile phases CH3 O CH3 HC OH H3C CH CH CH Testosterone Derivatives 3 3 CH3 OH 3 3 OH CH CH3 OH H3C OH 3 HC CH 3 CH3 H3C 3 OH CH CH O CH 3 OH 3 3 H3C H3C Boldione O O O O O Cl Desoxymethyltestosterone OH Cl O Methyltestosterone Boldenone CH3 Clostebol H3C O Dehydrochlormethyltestosterone Calusterone 6b Hydroxyboldenone CH3 Common Sports Doping Steroids Progesterones O Quinbolone Metabolic Pathway CH3 O CH CH CH3 O CH3 OH CH CH3 CH O 3 3 CH OH 3 3 OH 3 CH OH CH 3 CH HC CH3 5 3 3 CH3 H3C 3 O OH CH CH HN HO 3 3 CH3 OH N HO O CH3 CH H3C O O O 3 HO CH3 DHEA Estradiol CH Stanozolol Ethisterone Norethandrolone 3 Androstenedione 6 Methylandrostendione F 3 O O DHT Derivatives O CH 3 OH CH CH3 OH CH H3C 3 Tetrahydrogestrinone 3 CH3 OH Progesterone Fluoxymesterone CH3 OH O OH HC CH3 3 CH H3C HC CH 3 O 3 HO 3 H3C H3C 1 CH3 HN HO N O O Androgen Receptor Agonists O O 4 5 Androstenediol Dihydrotestosterone Metenolone Enanthate Mesterolone Testosterone CH O 3' Hydroxystanozolol HC CH OH 3 3 HO 3 OH CH H3C O 3 CH HO CH CH CH3 OH CH3 CH CH 3 3 3 CH 3 OH 3 CH3 CH H3C HC OH 3 CH3 CH 3 CH OH HO CH 3 3 H3C OH 3 OH CH3 H3C O F HO CH3 O Drostanolone Propionate 4 Androstenediol O O O O O HN OH 1 Testosterone O O Methyl 1 Testosterone Gestrinone Methandieone N Epitestosterone Formebolone 6b Hydroxyfluoxymesterone CH HC HO 3 O 3 OH CH3 OH CH3 O HC CH 3 CH CH 3 HC 3 CH3 3 OH CH3 HC 3 CH3 3 OH OH Prostanozol HC 3 O CH3 H3C CH HC 3 3 O O HO HO H3C CH3 OH 11b Hydroxyandrosterone CH3 CH3 Stenbolone 19 Norandrostenediol 19 Norandrostenedione OH HC HO O O 7 2 3 CH CH 1 O 3 Methandriol 3 OH Mestanolone HC HO CH 3 OH CH CH OH 3 OH Methasterone 3 3 Nandrolone Derivatives CH O Androsterone HC CH3 O CH H3C 3 3 OH 4 Hydroxytestosterone OH CH3 CH CH3 3 O O HC OH HO 3 H3C OH H3C 16a Hydroetiocholanolone O Mibolerone O O HO 1 Danazol 5a Androstanediol CH3 Nandrolone O O O 1= 3 Hydroxysteroid Dehydrogenase OH HO Oxandrolone Oxymesterone Oxabolone 2= 17b Hydroxysteroid Dehydrogenase HC CH CH3 O 3= Aromatase 3 OH O 3 O CH CH 4= 5a Reductase 3 O CH3 3 CH3 OH 5= 17, 20 Lyase OH H3C Norbolethone 6= 3b Hydroxysteroid Dehydrogenase CH CH3 CH CH 3 CH 7= Liver Metabolism 3 3 3 OH OH Cl CH CH3 3 O O CH3 OH NH N HO O O CH3 Trenbolone O 5a Androstanedione HO CH3 CH3 Methandrostenolone CH 19 Norandrosterone HN 3 Ethylestrenol Information Compiled forE. WSLA. Guice, by M.S. Formestane HO 2 H3C N Cl Furazabol O Clenbuterol Oxymetholone CH3 O CH3 HC OH H3C CH CH CH Testosterone Derivatives 3 3 CH3 OH 3 3 OH CH CH3 OH H3C OH 3 HC CH 3 CH3 H3C 3 OH CH CH O CH 3 OH 3 3 H3C H3C Boldione O O O O O Cl Desoxymethyltestosterone OH Cl O Methyltestosterone Boldenone CH3 Clostebol H3C O Dehydrochlormethyltestosterone Calusterone 6b Hydroxyboldenone CH3 Common Sports Doping Steroids Progesterones O Quinbolone Metabolic Pathway CH3 O CH CH CH3 O CH3 OH CH CH3 CH O 3 3 CH OH 3 3 OH 3 CH OH CH 3 CH HC CH3 5 3 3 CH3 H3C 3 O OH CH CH HN HO 3 3 CH3 OH N HO O CH3 CH H3C O O O 3 HO CH3 DHEA Estradiol CH Stanozolol Ethisterone Norethandrolone 3 Androstenedione 6 Methylandrostendione F 3 O O DHT Derivatives O CH 3 OH CH CH3 OH CH H3C 3 Tetrahydrogestrinone 3 CH3 OH Progesterone Fluoxymesterone CH3 OH O OH HC CH3 3 CH H3C HC CH 3 O 3 HO 3 H3C H3C 1 CH3 HN HO N O O Androgen Receptor Agonists O O 4 5 Androstenediol Dihydrotestosterone Metenolone Enanthate Mesterolone Testosterone CH O 3' Hydroxystanozolol HC CH OH 3 3 HO 3 OH CH H3C O 3 CH HO CH CH CH3 OH CH3 CH CH 3 3 3 CH 3 OH 3 CH3 CH H3C HC OH 3 CH3 CH 3 CH OH HO CH 3 3 H3C OH 3 OH CH3 H3C O F HO CH3 O Drostanolone Propionate 4 Androstenediol O O O O O HN OH 1 Testosterone O O Methyl 1 Testosterone Gestrinone Methandieone N Epitestosterone Formebolone 6b Hydroxyfluoxymesterone CH HC HO 3 O 3 OH CH3 OH CH3 O HC CH 3 CH CH 3 HC 3 CH3 3 OH CH3 HC 3 CH3 3 OH OH Prostanozol HC 3 O CH3 H3C CH HC 3 3 O O HO HO H3C CH3 OH 11b Hydroxyandrosterone CH3 CH3 Stenbolone 19 Norandrostenediol 19 Norandrostenedione OH HC HO O O 7 2 3 CH CH 1 O 3 Methandriol 3 OH Mestanolone HC HO CH 3 OH CH CH OH 3 OH Methasterone 3 3 Nandrolone Derivatives CH O Androsterone HC CH3 O CH H3C 3 3 OH 4 Hydroxytestosterone OH CH3 CH CH3 3 O O HC OH HO 3 H3C OH H3C 16a Hydroetiocholanolone O Mibolerone O O HO 1 Danazol 5a Androstanediol CH3 Nandrolone O O O 1= 3 Hydroxysteroid Dehydrogenase OH HO Oxandrolone Oxymesterone Oxabolone 2= 17b Hydroxysteroid Dehydrogenase HC CH CH3 O 3= Aromatase 3 OH O 3 O CH CH 4= 5a Reductase 3 O CH3 3 CH3 OH 5= 17, 20 Lyase OH H3C Norbolethone 6= 3b Hydroxysteroid Dehydrogenase CH CH3 CH CH 3 CH 7= Liver Metabolism 3 3 3 OH OH Cl CH CH3 3 O O CH3 OH NH N HO O O CH3 Trenbolone O 5a Androstanedione HO CH3 CH3 Methandrostenolone CH 19 Norandrosterone HN 3 Ethylestrenol Information Compiled forE. WSLA. Guice, by M.S. Formestane HO 2 H3C N Cl Furazabol O Clenbuterol Oxymetholone CH3 O CH3 HC OH H3C CH CH CH Testosterone Derivatives 3 3 CH3 OH 3 3 OH CH CH3 OH H3C OH 3 HC CH 3 CH3 H3C 3 OH CH CH O CH 3 OH 3 3 H3C H3C Boldione O O O O O Cl Desoxymethyltestosterone OH Cl O Methyltestosterone Boldenone CH3 Clostebol H3C O Dehydrochlormethyltestosterone Calusterone 6b Hydroxyboldenone CH3 Common Sports Doping Steroids Progesterones O Quinbolone Metabolic Pathway CH3 O CH CH CH3 O CH3 OH CH CH3 CH O 3 3 CH OH 3 3 OH 3 CH OH CH 3 CH HC CH3 5 3 3 CH3 H3C 3 O OH CH CH HN HO 3 3 CH3 OH N HO O CH3 CH H3C O O O 3 HO CH3 DHEA Estradiol CH Stanozolol Ethisterone Norethandrolone 3 Androstenedione 6 Methylandrostendione F 3 O O DHT Derivatives O CH 3 OH CH CH3 OH CH H3C 3 Tetrahydrogestrinone 3 CH3 OH Progesterone Fluoxymesterone CH3 OH O OH HC CH3 3 CH H3C HC CH 3 O 3 HO 3 H3C H3C 1 CH3 HN HO N O O Androgen Receptor Agonists O O 4 5 Androstenediol Dihydrotestosterone Metenolone Enanthate Mesterolone Testosterone CH O 3' Hydroxystanozolol HC CH OH 3 3 HO 3 OH CH H3C O 3 CH HO CH CH CH3 OH CH3 CH CH 3 3 3 CH 3 OH 3 CH3 CH H3C HC OH 3 CH3 CH 3 CH OH HO CH 3 3 H3C OH 3 OH CH3 H3C O F HO CH3 O Drostanolone Propionate 4 Androstenediol O O O O O HN OH 1 Testosterone O O Methyl 1 Testosterone Gestrinone Methandieone N Epitestosterone Formebolone 6b Hydroxyfluoxymesterone CH HC HO 3 O 3 OH CH3 OH CH3 O HC CH 3 CH CH 3 HC 3 CH3 3 OH CH3 HC 3 CH3 3 OH OH Prostanozol HC 3 O CH3 H3C CH HC 3 3 O O HO HO H3C CH3 OH 11b Hydroxyandrosterone CH3 CH3 Stenbolone 19 Norandrostenediol 19 Norandrostenedione OH HC HO O O 7 2 3 CH CH 1 O 3 Methandriol 3 OH Mestanolone HC HO CH 3 OH CH CH OH 3 OH Methasterone 3 3 Nandrolone Derivatives CH O Androsterone HC CH3 O CH H3C 3 3 OH 4 Hydroxytestosterone OH CH3 CH CH3 3 O O HC OH HO 3 H3C OH H3C 16a Hydroetiocholanolone O Mibolerone O O HO 1 Danazol 5a Androstanediol CH3 Nandrolone O O O 1= 3 Hydroxysteroid Dehydrogenase OH HO Oxandrolone Oxymesterone Oxabolone 2= 17b Hydroxysteroid Dehydrogenase HC CH CH3 O 3= Aromatase 3 OH O 3 O CH CH 4= 5a Reductase 3 O CH3 3 CH3 OH 5= 17, 20 Lyase OH H3C Norbolethone 6= 3b Hydroxysteroid Dehydrogenase CH CH3 CH CH 3 CH 7= Liver Metabolism 3 3 3 OH OH Cl CH CH3 3 O O CH3 OH NH N HO O O CH3 Trenbolone O 5a Androstanedione HO CH3 CH3 Methandrostenolone CH 19 Norandrosterone HN 3 Ethylestrenol Information Compiled forE.
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