Il controllo antidoping da Atene 2004 a Torino 2006



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!" # $% Il controllo antidoping da Atene 2004 a Torino 2006 Francesco Botrè Laboratorio Antidoping, FMSI, Rome, Italy

LOCATION

Prohibited classes and methods (The last WADA list, effective Jan 1st 2005) Prohibited classes of substances Stimulants, narcotics, anabolic agents (anabolic androgenic steroids & beta-2-agonists), diuretics, peptide hormones, mimetics and analogues, agents with anti-oestrogenic activity, masking agents, glucocorticoids, cannabinoids Prohibited methods Enhancement of oxygen transfer, pharmacological, chemical and physical manipulation, gene doping Classes of prohibited substances in certain sports Alcohol, beta-blockers www.wada-ama.org

Law n. 376/2000 ( Legge antidoping, 15.12.2000) I farmaci ( ) sono ripartiti in classi ( ) approvate con decreto del Ministero della Sanità, d intesa con il Ministero per i Beni e le Attività Culturali, su proposta della Commissione. ( )

Analytical laboratory Clinical chemistry: Matrices: any suitable biological material Aim: diagnostic tests test report based on: detection and quantitation of specific markers multiparametric profiles doubtful=positive (further investigation) Doping control analysis: Matrices: only urine for officially recognized tests Aim: to supply evidence test report based on: unambiguous identification of specific drugs/metabolites doubtful=negative (no further investigation)

The 33 ISO-IOC-WADA laboratories Africa: South Africa (Bloemfontein), Tunisia (Tunis) Americas: Brazil (Rio de Janeiro), Canada (Montreal), Colombia (Bogota), Cuba (La Habana), United States (Los Angeles) Asia: China (Beijing), S. Corea (Seoul), Japan (Tokyo), Malaysia (Penang), Thailand (Bangkok) Europa: Austria (Seibersdorf), Belgium (Ghent), Czech Republic (Prague), Finland (Helsinki), France (Paris), Germany (Cologne, Kreischa), Greece (Athens), Italy (Rome), Norway (Oslo), Poland (Sofia), Portugal (Lisbon), Russian Federation (Moscow), Spain (Barcelona, Madrid), Sweden (Stockholm), Switzerland (Lausanne), Turkey (Ankara), United Kingdom (Cambridge, London) Oceania: Australia (Sydney)\

Doping control laboratories must obtain and maintain accreditation ISO 17025 accreditation IOC-WADA accreditation ISO-IOC-WADA harmonization compliance with IOC-WADA ethical code

WAADS World Association of Anti-Doping Scientists Formed in 2001 All IOC accredited laboratories represented

SAMPLE RECEIPT - ALLOCATION REGISTRATION ( internal identification code) transport SAMPLE COLLECTION PROCEED ONLY IF CRITERIA FOR ACCEPTANCE ARE MATCHED, OTHERWISE INFORM THE RELEVANT AUTHORITIES (IOC-MC, WADA) { OPENING OF TRANSPORT BAGS AND OF EXTERNAL SEALS VISUAL INSPECTION (col, V, sediments ) / BOTTLE OPENING, ALIQUOTING, BATCHING NEW ALIQUOTING - SAMPLE PRETREATMENT SCREENING ANALYSIS SUSPECT SAMPLE SPECIFIC PRETREATMENT CONFIRMATION ANALYSIS NO CRITERIA FOR REVIEWING OF RESULTS CONFIRMATION MATCHED? YES NEGATIVE INTERNAL IDENTIFICATION OF SAMPLE (INTERNAL/EXTERNAL CODE) TEST REPORT

Updates/upgrades of the last four years 2001-2002 (IOC-MC) 2002-2003 (IOC-MC - WADA) 2003-2004 (WADA) 2004-2005 (WADA)

2002 (IOC MC) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous boldenone, clostebol, danazol, dehydrochlormethyltestosterone, drostanolone, fluoxymesterone, formebolone, mesterolone, metandienone, metenolone, methyltestosterone, nandrolone, norethandrolone, oxymesterone, oxandrolone, oxymetholone, stanazolol, trenbolone Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous dihydrotestosterone, epitestosterone, testosterone Other Anabolic Agents clenbuterol Peptide hormones choriogonadotropin (hcg) Beta-2-agonists fenoterol, salbutamol, terbutaline Diuretics & Masking agents acetazolamide, bendroflumethiazide, bumetanide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone Stimulants amfepramone, amphetamine, bromantan, caffeine, carphedon, cathine, cocaine, cropropamide, crotethamide, ephedrine, etamivan, etilefrine, fencamfamin, fenetylline, fenfluramine, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, methylephedrine, methylphenidate, nikethamide, pemoline, phendimetrazine, phentermine, pholedrine, phenylephrine, pipradol, prolintane, pseudoephedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, carteolol, labetalol, metoprolol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol

2003 (IOC - WADA) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous bolasterone, boldenone, clostebol, danazol, dehydrochlormethyltestosterone, drostanolone, fluoxymesterone, formebolone, mesterolone, metandienone, metenolone, methyltestosterone, mibolerone, nandrolone, norethandrolone, oxymesterone, oxandrolone, oxymetholone, stanazolol, trenbolone Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous dihydrotestosterone, epitestosterone, testosterone Other Anabolic Agents clenbuterol Peptide hormones choriogonadotropin (hcg) Beta-2-agonists bambuterol, fenoterol, salbutamol, terbutaline Diuretics & Masking agents acetazolamide, amiloride, bendroflumethiazide, bumetanide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone, HES Stimulants amfepramone, amphetamine, bromantan, caffeine, carphedon, cathine, clobenzorex, cocaine, cropropamide, crotethamide, ephedrine, etamivan, etilefrine, fencamfamin, fenetylline, fenfluramine, fenproporex, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, MDMA, methylephedrine, methylphenidate, nikethamide, pemoline, phendimetrazine, phenmetrazine, phentermine, pholedrine, phenylephrine, pipradol, prolintane, propylhexedrine, pseudoephedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, carteolol, carvedilol, labetalol, metoprolol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol Anti-oestrogens clomiphene, cyclofenyl, tamoxifen

2004 (WADA) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous bolasterone, boldenone, clostebol, danazol, dehydrochlormethyltestosterone, drostanolone, fluoxymesterone, formebolone, mestanolone, mesterolone, metandienone, metenolone, methyltestosterone, mibolerone, nandrolone, norbolethone, norethandrolone, oxymesterone, oxandrolone, oxymetholone, quinbolone*, stanazolol, stenbolone*, THG, trenbolone, 4- hydroxytestosterone*, Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous androstenediol, androstenedione, DHEA, dihydrotestosterone, epitestosterone, testosterone Other Anabolic Agents clenbuterol, zeranol Peptide hormones choriogonadotropin (hcg), erythropoietin (EPO) + RSR13 Beta-2-agonists bambuterol, fenoterol, formoterol, salbutamol, salmeterol, terbutaline Diuretics & Masking agents acetazolamide, amiloride, bendroflumethiazide, bumetanide, chlorothiazide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone, HES Stimulants amfepramone, amiphenazole, amphetamine, amphetaminil, benzphetamine, bromantan, caffeine, carphedon, cathine, clobenzorex, cocaine, cropropamide, crotethamide, DMA, ephedrine, etamivan, ethylamphetamine, etilefrine, fencamfamin, fenetylline, fenfluramine, fenproporex, furfenorex, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, MDMA, mephentermine, methylephedrine, methylphenidate, modafinil, nikethamide, pemoline, phendimetrazine, phenmetrazine, phentermine, pholedrine, phenylephrine, pipradol, prolintane, propylhexedrine, pseudoephedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, bunolol, carteolol, carvedilol, celiprolol, esmolol, labetalol, metoprolol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol Anti-oestrogens aminoglutethimide, anastrozole*, clomiphene, cyclofenyl, exemestane*, formestane*, letrozole*, tamoxifen Glucocorticoids* beclomethasone, betamethasone, budesonide, desonide, dexamethasone, fludrocortisone, flumethasone, flunisolide, fluocortolone, fluticasone, methylprednisolone, prednisolone, triamcinolone

2005 (WADA) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous bolasterone, boldenone, boldione, clostebol, danazol, delta1-androstene-3,17-dione* dehydrochlormethyltestosterone, drostanolone, ethylestrenol*, fluoxymesterone, formebolone, mestanolone, mesterolone, metandienone, metenolone, methyldienolone*, methyltrienolone*, methyltestosterone, mibolerone, nandrolone, norbolethone, norclostebol*, norethandrolone, oxymesterone, oxandrolone, oxymetholone, quinbolone*, stanazolol, stenbolone*, THG, trenbolone, 4-hydroxytestosterone*, 18a-homo-17b-hydroxyestr-4-en-3-one*, 4-hydroxy-19- nortestosterone Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous androstenediol, androstenedione, DHEA, dihydrotestosterone, epitestosterone, testosterone Other Anabolic Agents clenbuterol, zeranol Peptide hormones choriogonadotropin (hcg), erythropoietin (EPO) + RSR13 Beta-2-agonists bambuterol, fenoterol, formoterol, salbutamol, salmeterol, terbutaline Diuretics & Masking agents acetazolamide, amiloride, bendroflumethiazide, bumetanide, chlorothiazide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone, HES

2005 (WADA) Stimulants amfepramone, amiphenazole, amphetamine, amphetaminil, benzphetamine, bromantan, caffeine, carphedon, cathine, clobenzorex, cocaine, cropropamide, crotethamide, DMA, ephedrine, etamivan, ethylamphetamine, etilefrine, fampropazone, fencamfamin, fenetylline, fenfluramine, fenproporex, furfenorex, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, MDMA, mephentermine, methylephedrine, methylphenidate, modafinil, nikethamide, pemoline, phendimetrazine, phenmetrazine, phentermine, pholedrine, phenylephrine, pipradol, prolintane, propylhexedrine, pseudoephedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, bunolol, carteolol, carvedilol, celiprolol, esmolol, labetalol, metoprolol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol Anti-oestrogens aminoglutethimide, anastrozole*, clomiphene, cyclofenyl, exemestane*, formestane*, fulvestrant*, letrozole*, raloxifene*,tamoxifen, testolactone*, toremifene* Glucocorticoids beclomethasone, betamethasone, budesonide, desonide, dexamethasone, fludrocortisone, flumethasone, flunisolide, fluocortolone, fluticasone, methylprednisolone, prednisolone, triamcinolone Alpha-reductase inhibitors Finasteride, dutasteride

2002 (IOC MC) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous boldenone, clostebol, danazol, dehydrochlormethyltestosterone, drostanolone, fluoxymesterone, formebolone, mesterolone, metandienone, metenolone, methyltestosterone, nandrolone, norethandrolone, oxymesterone, oxandrolone, oxymetholone, stanazolol, trenbolone Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous dihydrotestosterone, epitestosterone, testosterone Other Anabolic Agents clenbuterol Peptide hormones choriogonadotropin (hcg) Beta-2-agonists fenoterol, salbutamol, terbutaline Diuretics & Masking agents acetazolamide, bendroflumethiazide, bumetanide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone Stimulants amfepramone, amphetamine, bromantan, caffeine, carphedon, cathine, cocaine, cropropamide, crotethamide, ephedrine, etamivan, etilefrine, fencamfamin, fenetylline, fenfluramine, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, methylephedrine, methylphenidate, nikethamide, pemoline, phendimetrazine, phentermine, pholedrine, phenylephrine, pipradol, prolintane, pseudoephedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, carteolol, labetalol, metoprolol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol

2005 (WADA) Anabolic Agents: Anabolic Androgenic Steroids (AAS): exogenous bolasterone, boldenone, boldione, clostebol, danazol, delta1-androstene-3,17-dione* dehydrochlormethyltestosterone, drostanolone, ethylestrenol*, fluoxymesterone, formebolone, mestanolone, mesterolone, metandienone, metenolone, methyldienolone*, methyltrienolone*, methyltestosterone, mibolerone, nandrolone, norbolethone, norclostebol*, norethandrolone, oxymesterone, oxandrolone, oxymetholone, quinbolone*, stanazolol, stenbolone*, THG, trenbolone, 4-hydroxytestosterone*, 18a-homo-17b-hydroxyestr-4-en-3-one*, 4-hydroxy-19- nortestosterone Anabolic Agents: Anabolic Androgenic Steroids (AAS): endogenous androstenediol, androstenedione, DHEA, dihydrotestosterone, testosterone Other Anabolic Agents clenbuterol, zeranol Peptide hormones choriogonadotropin (hcg), erythropoietin (EPO) + RSR13 Beta-2-agonists bambuterol, fenoterol, formoterol, salbutamol, salmeterol, terbutaline Diuretics & Masking agents acetazolamide, amiloride, bendroflumethiazide, bumetanide, chlorothiazide, chlortalidone, etacrynic acid, furosemide, hydrochlorothiazide, indapamide, spironolactone, triamterene, canrenone, HES Stimulants amfepramone, amiphenazole, amphetamine, amphetaminil, benzphetamine, bromantan, carphedon, cathine, clobenzorex, cocaine, cropropamide, crotethamide, DMA, ephedrine, etamivan, ethylamphetamine, etilefrine, fampropazone, fencamfamin, fenetylline, fenfluramine, fenproporex, furfenorex, heptaminol, mefenorex, mesocarb, methamphetamine, methoxyphenamine, MDA, MDMA, mephentermine, methylephedrine, methylphenidate, modafinil, nikethamide, pemoline, phendimetrazine, phenmetrazine, phentermine, pholedrine, pipradol, prolintane, propylhexedrine, selegiline, strychnine Narcotics + Cannabinoids buprenorphine, methadone, morphine, pentazocine, pethidine, THC Beta-blockers acebutolol, alprenolol, atenolol, betaxolol, bisoprolol, bunolol, carteolol, carvedilol, celiprolol, esmolol, labetalol, nadolol, oxprenolol, pindolol, propranolol, sotalol, timolol Anti-oestrogens aminoglutethimide, anastrozole*, clomiphene, cyclofenyl, exemestane*, formestane*, fulvestrant*, letrozole*, raloxifene*,tamoxifen, testolactone*, toremifene* Glucocorticoids beclomethasone, betamethasone, budesonide, desonide, dexamethasone, fludrocortisone, flumethasone, flunisolide, fluocortolone, fluticasone, methylprednisolone, prednisolone, triamcinolone Alpha-reductase inhibitors Finasteride, dutasteride

Antidoping analysis: 3 main areas Pre-instrumental stage: sample pretreatment and preliminary measurements (V, colour, sediments, ph, sg) Screening (GC-NPD, GC-MS, HPLC, LC- MS, immunological techniques ) Confirmation (GC-MS, GC-HRMS, GC-MS- MS, GC-HRMS-MS, GC-C-IRMS, LC-MS- MS ) + EPO/NESP Increasing complexity ( cost and time per sample)

Complexiy Confirmation analysis Screening analysis Hot area Reliability

Total number of targets for screening (minimum requested to pass the reaccreditation test or the PT) 92 in 2002 106 in 2003 150 in 2004 165 in 2005 over 200 in 2006?

2002 (6500 A urines) Stim (free) Stim (conj), bbloc Hormones (free) Hormones (total) LCAA Diur&Mask hcg, DOA GC-NPD GC-MS-NCI GC-MS GC-MS HRMS GC-MS IA

2002 (6500 A urines) 2003 (7000 A urines) Stim (free) GC-NPD Stim (free) GC-NPD Stim (conj), bbloc GC-MS-NCI Stim (conj), bbloc GC-MS-NCI Hormones (free) GC-MS Hormones (free) GC-MS Hormones (total) GC-MS Hormones (total) GC-MS LCAA HRMS LCAA HRMS Diur&Mask GC-MS Diur&Mask GC-MS hcg, DOA IA hcg, DOA IA HES GC-MS

2002 (6500 A urines) 2003 (7000 A urines) Stim (free) GC-NPD Stim (free) GC-NPD Stim (conj), bbloc GC-MS-NCI Stim (conj), bbloc GC-MS-NCI Hormones (free) GC-MS Hormones (free) GC-MS Hormones (total) GC-MS Hormones (total) GC-MS LCAA HRMS LCAA HRMS Diur&Mask GC-MS Diur&Mask GC-MS hcg, DOA IA hcg, DOA IA HES GC-MS 2004 (7800 A urines + 600 EPO + blood) Stim (free) Stim (conj), bbloc Hormones (free) Hormones (total) LCAA Diur&Mask hcg, DOA HES Glucocort, THG EPO GC-NPD GC-MS GC-MS GC-MS HRMS GC-MS IA GC-MS LC-MS Flaminia

2002 (6500 A urines) 2003 (7000 A urines) Stim (free) GC-NPD Stim (free) GC-NPD Stim (conj), bbloc GC-MS-NCI Stim (conj), bbloc GC-MS-NCI Hormones (free) GC-MS Hormones (free) GC-MS Hormones (total) GC-MS Hormones (total) GC-MS LCAA HRMS LCAA HRMS Diur&Mask GC-MS Diur&Mask GC-MS hcg, DOA IA hcg, DOA IA HES GC-MS 2004 (7800 A urines + 600 EPO + blood) 2005 (>8000 with 10% EPO planned) Stim (free) GC-NPD Stim (free) Stim (conj), bbloc GC-MS Stim (conj), bbloc Hormones (free) GC-MS Hormones (free) Hormones (total) GC-MS Hormones (total) LCAA Diur&Mask HRMS GC-MS LCAA Diur&Mask? hcg, DOA IA hcg, DOA HES GC-MS HES Glucocort, THG LC-MS Glucocort, THG EPO Flaminia EPO Blood

Screening analysis of a real sample (diclophenamide?)

Confirmation analysis (sample vs. positive reference urine)

Screening V 1999-2002 Urine volume 5mL Internal standard Indomethacine, 200 ng/ml Extraction Sep-pak C18 cartridge Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg 70 C C 180 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V 2002-2003 Urine volume 5mL Internal standard Indomethacine, 200 ng/ml Extraction Sep-pak C18 cartridge Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 900W 10 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V 2004 Urine volume 5mL Internal standard Indomethacine/mefruside 1st Extraction No cartridge! ph corrected to 10 (800 µl carbonate/bicarbonate 4M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C 2nd Extraction No cartridge! ph corrected to 4 (100 µl formate/formic acid 5M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 1200W 6 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V present Urine volume 6 ml Internal standard Indomethacine/mefruside 1st Extraction No cartridge! ph corrected to 10 (800 µl carbonate/bicarbonate 4M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C 2nd Extraction ph corrected to 4 (100 µl formate/formic acid 5M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 1200W 6 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V present Urine volume 6 ml Internal standard Indomethacine/mefruside 1st Extraction No cartridge! ph corrected to 10 (800 µl carbonate/bicarbonate 4M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C 2nd Extraction ph corrected to 4 (100 µl formate/formic acid 5M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 1200W 6 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V present Urine volume 6 ml Internal standard Indomethacine/mefruside 1st Extraction No cartridge! ph corrected to 10 (800 µl carbonate/bicarbonate 4M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C 2nd Extraction ph corrected to 4 (100 µl formate/formic acid 5M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 1200W 6 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM

Screening V present Urine volume 6 ml Internal standard Indomethacine/mefruside 1st Extraction No cartridge! ph corrected to 10 (800 µl carbonate/bicarbonate 4M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C 2nd Extraction ph corrected to 4 (100 µl formate/formic acid 5M) extraction by 12 ml CHCl 3 :isopropanol:tbme (80:10:10) Evaporation N 2 stream, 40 C Derivatization Acetone/CH 3 I= 1/9, 200 µl Anhydrous K 2 CO 3, 50 mg MW 1200W 6 min Injection volume 1 µl (split 1:10) Analysis GC-MS EI SIM 1/2 goes to IVa

Recombinant EPO Endogenous EPO Darbepoetin (NESP)

Microwaves, orientation of the magnetic field and rotational energy

Microwaves cook from the inside Text > Tint Text < Tint

Ideal derivatization reaction Microwaves diuretics, stimulants glucocorticoids

The tradition: Select an appropriate derivatization reagent Test everything you use (tubes, racks, septa) Work in segmented steps (i.e. 30 = 10 +10 +10 ) Ensure thermostatic control (simplest way: put the reaction chamber(s) into a water bath inside the oven) Use technical ovens Keep a fire estinguisher at hand

7,00E+04 6,00E+04 5,00E+04 4,00E+04 3,00E+04 2,00E+04 1,00E+04 0,00E+00 time mw T Unspecific (methylation) 3,E+05 3,E+05 2,E+05 2,E+05 1,E+05 5,E+04 0,E+00 time mw T Specific (silylation)

Application of microwaves in derivatization reactions

OSSIMORO Una figura retorica in cui si accostano due termini in forte antitesi fra loro in modo da creare un originale contrasto, talvolta con sorprendenti effetti linguistici chiaramente ambiguo urlo silenzioso, silenzio assordante affollata solitudine insostenibile leggerezza definitively maybe

L ossimoro più famoso della lingua italiana ghiaccio bollente

On the boiling T of water (at 1 atm) conventional heating: 100.0 C microwave irradiation, 1200 W: 103.5 C microwave irradiation, 1200 W, + boiling chips: 100.0 C This superheating effect has been attributed to retardation of nucleation during microwave heating The effect is eliminated in well stirred mixtures and using low microwave power (< 800 W) In theory, a sufficiently strong magnetic field could cause the solvent to freeze In practice, the effect is minimal, but detectable

The tested racks & water bath

The tested racks & water bath

Preliminary results (waiting for the oven )! " # $ %&'! ( ) *

Preliminary results (waiting for the oven ) %FLUOCORTOLONE-3TMS usp Time (min) Thermal 100 C MW in water MW dry 15 24%BUDESONIDE-3TMS 18 usp 95 30Time 45 (min) 60 15 30 Time (min) 45 15 60 Time 30 (min) 45 15 60 30 45 60 Time (min) Thermal 32 18 MW 34 100 C in 35 water 40 %MPREDNISOLONE-4TMS 11 43 9 usp Thermal 15 9MW 100 C in water 18 14 %PREDNISONE-3TMS usp 15 6 26 12 Thermal MW 13 8 100 C in water 15 17 8 9 18 6 15 9 %PREDNISOLONE-4TMS usp 19 Thermal 28 MW 36 100 C 10in water 81 MW 97 dry 99 75 72MW dry 87 81 88 80 86 76 MW dry 91 92 100 100 MW dry 15 5 3 62 30 5 3 65 45 12 4 90 60 6 2 89

Preliminary results (waiting for the oven )!!!" # $!! % & #! #!"'()*%+ (!!,! #!!-.-!! #,!!! $!$ / #0! # #"! %

From urine to blood: key issues +,-!! "... / 0 10( * 2 3 (+* 4 1!".! 5! )

! HBOCs hgh Robust and reliable procedure (visual screening + different confirmation) Lack of reference materials The procedure is reliable, but not robust Reagents not available in sufficient amounts Presently going from lab to industrial scale Blood Transfusions The procedure is reliable, but not robust No interlaboratory study so far

Acknowledgements Cristiana Colamonici, Flaminia Garribba, Monica Mazzarino National Italian Antidoping Commission (supporting the research activity of the lab in its entirety) The Athens, Barcelona, Koeln, Lausanne, London and Seibersdorf Laboratories