Index

A 5a-Androstanediol, 87 AAS. See Anabolic-androgenic steroids Androstenediol, 157 Abnormal blood profile score, 302, 308, Androstenedione, 27, 86–87, 157 318, 321, 322 Androsterone, 27, 52–53, 68, 79, 84–92, ABPS, See Abnormal blood profile score 104, 133, 147, 158, 340 Accreditation, 375 Anemia, 252 Addiction, 478 Animal welfare, 370 Adrenal cortex, 34 Anti-androgen, 168 Adrenal glands, 34 Anti-doping convention, 12, 515 Adrenoreceptors, 228, 229 Anti-estrogens, 444, 469 Adverse analytical finding, 3, 26, 78, 114, Anti-inflammatory drugs, 341 129, 132, 143, 159, 170, 192, 231, 239, 529 Antithrombin III, 438 Adverse effects, 465, 256, 263, 343, AORC. See Association of Official racing 412–484 Chemists Aggravating circumstances, 520 APCI See Atmospheric pressure chemical Aggressiveness, 231, 476 ionization b-Agonists, 228–233, 237–243, 362 API See Atmospheric pressure ionization Albumin, 47, 344 Apolipoproteins, 440 Aldosteron, 427 Application site, 363 17a-Alkylation, 102, 461 Arbitration, 528–529 Allopregnanolone, 476 Aromatase, 36–37, 101, 461 Amino acids, 47, 65, 111, 192, 204, Aromatization, 26 36–39, 44, 143–145, 436, 211–222, 255–262, 496–497 461, 469–470 Amphetamine, 5, 130, 231, 234, 444, 478 Arrhythmias, 444 Anabolic-androgenic steroids (AAS), Arsenic, 3, 380 26–53, 66, 101–117, 130, 411–447, Arteriosclerosis, 172, 434–435, 467–468, 459–474 473 Androgen receptor, 27–28, 40–42, 110–114, Association constant, 48 134, 168, 460, 469 Association of Official racing Chemists Androgens (AORC), 374 endogenous, 25, 77–93 Atherosclerotic coronary artery disease, exogenous, 49 413 metabolism, 51–54, 66–73, 102–109 Atherothrombosis, 440

533 534 Index

Athlete Passport, 264–265, 299–303, Catecholamines, 229–230, 447 305–325, 341, 508 CERA. See Continuous Erythropoietin Atmospheric pressure chemical ionization Receptor Activator (APCI), 244 Cholestatic jaundice, 465, 472 Atmospheric pressure ionisation (API), Chromatograms, 90, 116–117, 172–177, 398, 399 281, 376 Atrial fibrillation, 445 Clenbuterol, 6, 115, 238–239, 360, 364, 445 Autologuous blood doping, 10 Clostebol, 103, 157, 164, 166, 396–397 Cocaine, 2–5, 233, 235, 522 B Collagen, 437 BALCO. See Bay Area Laboratory Collision-induced dissociation, 280, 337 Cooperative (BALCO) Community Reference Laboratory (CRL), Bay Area Laboratory Cooperative 362 (BALCO), 158–159, 516, 518 Confirmation, 90, 114, 132, 192–195, Bayesian approach, 315 218–219, 242, 271, 333–338, 384, 529 Bayesian network, 316 Contamination, 128, 141, 170, 340, 382, B-chain, 211–222 388, 501 Beta-agonists, See b-Agonists Continuous Erythropoietin Receptor Biceps, 431 Activator (CERA), 260–261, 271 Biological passport, See Athlete Passport Controlled Substance, 515 Biosimilar Epoetins, 260–261 Coregulators, 40–42 Biosynthesis, 32–35 Coronary artery disease, 413–414, 434, 440, Blood pressures, 257, 412–413, 427–432, 446, 474, 500 465–466 Coronary calcification, 434–435 diastolic, 109, 411, 413, 427–431, 446 Coronary heart disease (CHD), 443 systolic, 413, 428–431 Coronary sclerosis, 466 Blood sample collection, 311 Corticosteroids, 174, 230, 400–402, 461, 498 Blood transfusion Court of Arbitration for Sport (CAS), 13, allogeneic, 296 514, 519 autologous, 232, 252, 296 CYP19 See Aromatase homologous, 232, 252, 297–299, 303 C-peptide, 211 Detection, 297–303 C3-plants, 89 Boar tissue, 364 C4-plants, 89 d 13 Bodybuilder, 460 C value, 78 Boldenone, 384, 393 Cytochrome P450, 31–34, 37, 44, 102, 134, Bovine meat, 356 144, 462, 475 Bromantan, 10, 521 BRP-EPO, 278 D Danazol, 103, 157, 182, 396–397 C Darbepoetin alfa, 238, 259–260, 495 Capsaicin, 372 Decision limit (DL), 133 Carbon dioxide, 383 Degradation, 41, 71, 82, 119, 299, 261, 284, Cardiomyopathy, 412, 423, 444, 465 299, 463, 476, 490, 483 Cardiovascular, 108–109, 190, 371, Dehydrochlormethyltestosterone, 103, 182 412–447, 464–465, 474 Dehydroepiandrosterone (DHEA), 27–39, Carphedone, 10 53, 69, 86–91, 157, 180, 462 CAS. See Court of Arbitration for Sport dehydroepiandrosterone-3b-sulfate, 69, 81 Catabolism, 51–53 Dehydrogenase, 36–37, 102, 229, 471 Index 535

Delivery Vector, 502–504 Epimerisation, 28, 105–108, 394–396 11-Deoxycorticosterone (DOC), 427 Epitestosterone, 28, 30, 39–54, 68, 82–84, Derivatization, 101, 114, 117, 277, 282, 335, 160, 338–341, 523 340, 347 Epitope, 191–192, 195 Chiral, 241 Epoetin methylation, 335–336 alfa, 258–260, 266–282, 495, 523 trimethylsilylation, 80, 114, 335, 340 beta, 258–260, 266–277, 495 Dextran, 345 delta, 259, 261, 271, 284–286 DHEA. See Dehydroepiandrosterone omega, 258–259, 272–273 DHT. See 5a-Dihydrotestosterone Erythrocytes, 253, 263 Diastolic filling, 422 Erythropoiesis, 13, 254, 260, 264, 299, 303, Dietary supplements, See Nutritional 325, 495 supplements Erythropoietin (EPO), Diethylstilbestrol, 361 analogues, 258–262 Dihydrotestosterone (DHT), 25, 35–37, 66, antibody, 267–272, 284–285 86, 101, 111, 137, 161, 342, 461 endogenous, 254, 258, 261–262, 266, 5a-Diol. See 5a-Androstanediol 269, 283 Discriminating power, 318 half life, 258–261, 267 Distribution function, 318, 319 receptor, 253–255, 260–264 Diuretics, 176, 329–337 recombinant, 262, 264–286, 307 carbonic anhydrase inhibitors, 329 synthesis, 253–254, 262 loop, 329 urinary, 264–268, 276 potassium-sparing, 329 Escherichia coli (E.coli), 71, 81, 395 DNA barcode, 507 ESI. See Electrospray ionization DNA microarrays, 506 Estradiol, 36–48, 78, 144–145, 356–365, Documentation Packages, 523 401, 436, 462, 469–472 Dopamine, 228–230, 236–237, 385, 476 17b-Estradiol. See Estradiol Doping Estrogens, 28, 49–51, 143, 164, 444, definitions, 15–18, 517–518 469–472 gene, 11, 358, 402, 490–508 Etiocholanolone, 27–28, 52–53, 68, 84, violations, 519–22, 529 88–92, 146, 340 Doppler flow velocity, 424 Excretion, 51–54, 71, 87–88, 130–135, Double-blotting, 268 144–146, 329–333 Drug metabolism, 373–374 Expert witnesses, 528 Drug withdrawal, 429, 465, 478 External quality assessment system, 524 Dynepo. See Epoetin, delta Extraction liquid-liquid, 110, 240–241, 333, 340, E 347, 400 Echocardiographic parameters, 416 solid-phase, 80, 220–221, 240, 273, Electrophoresis, 272 334–336, 376, 397–398 Electrospray ionization (ESI), 80, 202, 217, 244, 278 F ELISA. See Enzyme linked immunosorbant Fast atom bombardment (FAB), 274 assay Feeding experiments, 380 Endothelial dysfunction, 432 Ferritin, 256–257, 296 Enzyme linked immunosorbant assay Finasteride, 45, 91, 141, 342–344, 477 (ELISA), 267, 282, 377, 488–489 Flow cytometry, 297–301 Epimer, See Epimerisation Flow-mediated dilatation (FMD), 432 536 Index

Fluoxymesterone, 47–48, 103, 162, 360, H 397, 477 Haematocrit, 256, 307, 313, 344 Follicle-stimulating hormone (FSH), 42–45, Haemostasis, 438 110, 465, 471 Health risks, 412–415, 465, 500 Formebolone, 103, 157 Helix pomatia, 81, 381 Fragmentation, 175–176, 218, 244–245, Hemodilution, 308 336, 401 Hemoglobin, 262–265, 302, 307, 325, 507, Furazabol, 103, 166, 182, 464 total mass, 299–300 Hepatic failure, 471–473 Hepatic triglyceride lipase (HTGL), 441 G hGH. See Human growth hormone GABA, 234, 475–476 High density lipoprotein (HDL), 471–473 Gas chromatography (GC), High performance liquid chromatography GC–MS 78, 114–115, 131, 171–173, (HPLC), 91, 221, 244–245, 274–283, 241–243, 335–336 341, 372 GC/C/IRMS, 88–93, 146 High resolution mass spectrometry GC–MS. See Gas chromatography–mass (HRMS), 115, 142, 171, 217, 242, 399 spectrometry Horseracing, 370 Gel electrophoresis, 204 HPG. See Hypothalamus–pituitary–adrenal Gene HPLC. See High performance liquid doping, 347, 358, 402, 485–508 chromatography therapy, 487–489 Humalog, 218–222 delivery, 490 Human growth hormone (hGH), 187, 188 Genetic deletion, 70 effects 190–191 Genetic polymorphism, 54, 70–73, 82, 338, half life, 188, 192, 193 500 isoforms, 194–195 GH-releasing hormone (GHRH), 498 recombinant, 188 Glucuronic acid, 52–53, 66, 105, 108, 112, Hydrolysis, 53, 71, 81, 111, 240, 344–347, 401 131, 240, 341, 341–342, 393–395 Hydroxyethyl starch (HES), 261, 345 b-Glucuronidase, 53, 71, 81, 114, 340, 397 Hydroxylation, 52, 104, 112, 254, 261, Glucuronidation, 34, 66–68, 105, 146, 338, 330–331, 394–396, 462–463 472, 504 Hydroxysteroid dehydrogenases (17bHSD, O-Glycan, 266, 276 3b HSD), 32–35, 40, 462–463 N-Glycans, 259, 273, 277–278, 283 Hyperglycemia, 214–215, 471 Glycogen, 214, 230 Hypertension, 257, 427–431, 465–467, 495 Glycoprotein, 48, 258–262, 275, 297, 439, Hypogonadism, 112, 471 495–496 Hypothalamus, 42–45, 462, 470, 471, 498 Glycosylation, 206, 256–260, 276 Hypothalamus–pituitary–gonadal axis GnRH. See Gonadotropin releasing (HPG), 47, 461 hormone (GnRH) Hypoxia-inducible factor, 2531, 498 Gonadotropic hormones, 461 Gonadotropins, 42–47, 133, 445, 470 I Gonadotropin releasing hormone (GnRH), IEF, See Isoelectric focussing 43–45, 462 IEF-profile, 261, 267–272 Greyhound racing, 361, 370 IGF-1. See Insulin-like growth factor 1 Growth hormone (GH), 188–195, 204–206, IGF binding protein 3 (IGFBP 3), 193, 202 312, 377, 430, 498 Immunoaffinity purification, 202, 218, 221, Gynecomastia, 469 262, 267, 271, 282, 285 Index 537

Immunoassay, See also radioimmunoassay, Isoelectric focussing (IEF), 252, 256, 9, 49, 51, 80, 191–194, 284 260–261, 266–271, 523 Implants, 356–361 Isoforms, 32, 69, 192–196, 204, 257–285 In-competition tests, 239, 285 Isomerase, 32, 35, 81 Individual variations, Isotope ratio mass spectrometry (IRMS), 6, Inter, 71, 88, 310, 316 9, 80, 88–93, 146, 386–388 Intra, 84, 316, 518 Infertility, 46, 110, 165 K Inflammatory effect, 434 Ketoconazole, 6, 44, 79 Inhibitors, 341, 475 ACE, 500 L aromatase, 144, 181 Laboratory Information Management carbonic anhydrase, 329, 332 System (LIMS), 374 GABA, 477 LC–MS/MS. See Liquid chromatography GATA-2, 262 tandem mass spectrometry hydroxylase, 261 Left-ventricular hypertrophy, 412–414, 420, insulin secretion, 214 446, 466 myostatin, 495 Left ventricular myocardial contractile plasminogen activator, 438 function, 425 platelet aggregation, 437 Left ventricular wall thicknesses, See Left- protease, 267, 272, 283 ventricular hypertrophy reductase, 45, 78, 89–90, 141, 328, Leydig cells, 28, 35, 42 342–344 LH. See Luteinising hormone re-uptake, 237 Ligand-binding domain, 41, 111, 177, 460 Insulin, 209–223 LIMS. See Laboratory Information analogs, 215, 218, 220, 222 Management System biosynthesis, 211 Lipid metabolism, 440–444, 473 degradation, 215 Lipoproteins, 31, 109, 427, 440–444, metabolism, 215–217 471–473 resistance, 214, 498 Liquid chromatography tandem mass secretion, 212–214, spectrometry (LC–MS/MS), See Tandem synthetic, 202, 218–223 mass spectrometry Insulin-like growth factor 1 (IGF-1), List of prohibited substances, See Prohibited 191–194, 201–206, 253, 325, 487, 499 List Internal standards, deuterated, 172, 243, Luteinising hormone (LH), 29–31, 42–47, 399, 401 86, 109, 143, 461, 465, 471 IOC Medical Commission, 8, 378 Ion exchange chromatography, 273, 277 Ionization M Atmospheric pressure chemical Madol, 178, 180f ionization (APCI), 244–246 Ma Huang, 2, 233 electron impact (EI), 336, 372 MALDI-TOF mass spectrometry, 273–282, electrospray (ESI), 71, 80, 117, 202, 217, 347 244, 274, 278, 337 Marker approach, 193 Ion trap mass spectrometry, 175, 245, 278, Masculanizing, 26, 468 282, 340, 400 Masking agent, 78, 90, 327–347, 371, 444 Ischemia-induced arrhythmia, 447 Matrix-assisted laser desorption ionization ISO 17025 standard, 9, 311, 375, 387 (MALDI), 217, 274, 346–347, 402 538 Index

Maximum residue level, 357, 361 381–382, 393–398, 401, 420, 447, 468, MDMA. See 470, 519 Methylenedioxymethamphetamine Nandrolone decanoate, 135, 421, 430, 446, Measurement uncertainty, 243 470 Melengestrol acetate, 357 National Anti-Doping Organisation Menstrual cycle, 29, 43, 46, 84, 143–144 (NADO), 14 estanolone, 103, 157, 396f Negative feedback, 43–46, 79, 194, 381, Mestanolone, 103, 164–165, 396–397, 461, 470 468–469 NESP, See darbepoetin alfa Metabolism Neurosteroids, 460–462, 474–477 hepatic, 46 Non-genomic pathway, 49 phase-I, 66, 71, 102–104, 129, 131–132, Noradrenaline, 228, 427 374, 394–395 Norandrostenediol, 104, 131–134, 137, 157 phase-II, 52, 65–73, 105, 374, 395 Norandrostenedione, 26, 37–38, 104, Metandienone, methandienone, 47, 131–134, 137–138, 343 100–106, 157, 161, 163, 396–397, 427, Norandrosterone, 38–39, 114–115, 441, 464, 468–470 128–148, 163, 170, 343, 523 Methamphetamine, 5, 232, 234–238, Norbolethone, 90, 104, 157–158, 160, 162, 240–241, 522 172–173 Methandriol, 103, 157, 397 Norclostebol, 104, 157, 164 Methasterone, 103, 157, 179 Norethandrolone, 104, 157, 163, 172, 359, Methenolone, 103, 157, 172, 396–397, 400, 395–396 468–469, 472 Norethisterone, 133, 139–141 Methylenedioxymethamphetamine Nortestosterone, See Nandrolone (MDMA), 231 19-Nortestosterone, See Nandrolone Methyltestosterone, 48, 100–106, 157, Novolog Aspart, 215, 222 164–165, 172, 176, 395–397, 468, 470 Nutritional supplements, 2, 30, 79, 92, Methyltrienolone, 104, 157, 163f 136–139, 159, 164–170, 178–182, 232, Minimum required performance limit 235, 339, 382 (MRPL), 117, 233, 239, 242, 523 MIRCERA. See Continuous Erythropoietin O Receptor Activator Octadecylsilane columns, 336 Monoamine reuptake inhibition, 230 OFF model, 264–265 MRM. See Multiple reaction monitoring Oligosaccharides, 273 MRPL. See Minimum required performance ON model, 264–265 limit Orbitrap, 245–246, 283 Multiparametric approach, 307–308, 325 Out-of competition test, 141, 196, 239, 300, Multiple reaction monitoring (MRM), 175, 321–322, 403, 502, 518, 520 337, 399–400 Oxabolone, 104, 157, 468 Myocardial fibroses, 466–467 Oxandrolone, 104, 157, 438–439, 463, 468 Myocardial hypertrophy, 415, 426, 465–466 Oxygen transport, 10, 253, 296, 307 Myocardial infarction, 109, 412, 432, 442, Oxymesterone, 104, 157, 172 465–467 Oxymethelone, 104, 157, 161, 172, Myostatin, 487, 499–504 396–397, 441, 468–470

N P Nandrolone, 36–39, 104, 114, 127–148, Peptide hormones, 10, 43, 191–192, 201–204, 157–163, 170, 172, 343, 363–364, 378, 210–213 Index 539

Peripheral arterial thromboses, 435 Estrogen, 28, 460, 469–470 Peroxisome proliferator-activated GABAA, 460 receptor delta (PPAR-d), 487 GnRH, 43 Phase-II metabolism, 65–73, 105, Growth hormone,187 374, 395 Glucocorticoid, 460 Phase-I metabolism, 66, 71, 102–104, 129, Insulin, 213 131–132, 374, 394–395 Mineralcorticoid, 460 Phenylpiracetam. See Carphedone PPAR-d, See Peroxisome proliferator- pI-value, 266 activated receptor delta Plasma expander, 328, 344f Progesterone, 460, 469 Plasma proteins, 50, 344 Transferrin, 10, 264, 308 Plasminogen, 437f Thromboxane A2, 436–437, 439 Plasminogen activator inhibitor (PAI), 438 Recombinant human erythropoietin Platelet aggregation, 436–437, 439 (rhEPO), 251–286, 296, 303 Poppy seeds, 382f Red blood cell, 252–253, 256, 296, PPAR-d. See Peroxisome proliferator- 302–303, 308, 328, 496 activated receptor delta 5a-Reductase, 35–40, 91, 101, 111, 134, Precursor ion scan, 119, 176, 245 141, 342–344, 475 Probenecid, 78, 328, 337, 341f 5a-Reductase inhibitors, 45, 78, 89–90, 141, Product ion spectrum, 117–119, 175, 205, 328, 342–344 220, 222 5a-Reduction, 26, 37, 44, 468 Progesterone, 32, 34, 355, 462, 475 Reference Laboratories, 357, 361–362 Progestins, 139, 141, 164 , 177 Reference materials, 65, 159, 174, 387 Prohibited list, 10–16, 129, 137, 156–157, Reference ranges, 79, 82–85, 92, 193, 264, 507 210, 228, 252, 328, 347, 370, 48, 514, Regional Anti-Doping Organisations 520–522 (RADOs), 14 Prohormones, 25, 30, 36, 40, 130, 136–139, Related compounds, 156, 231, 329, 521 148, 158, 211 Repoxygen, 498 Proinsulin, 211 Residue analysis, 357 Prosecutor’s fallacy, 320 Reticulocytes, 10, 253, 264, 302, 308, 313, Prostanozol, 104, 157, 180, 182 323 Protein metabolism, 214 Reuptake, noradrenaline, 229 Psychostimulants, 234, 521 rhEPO. See Recombinant human PVDF-membrane, 268 erythropoietin RSR13, 10 Q Quality control, 81, 137–138, 313, 375, 387 S Quinbolone 104, 157, 359 Salbutamol, 237, 433 Salicylic acid, 378 R SARMs. See Selective androgen receptor Radioimmunoassay, Sea also immunoassay, modulators 80, 114, 131, 191, 384, 393, 515 Screening, 9, 71, 78, 80, 114–115, 120, Receptors, 110–111 171, 192, 240–242, 269, 299, 333–338, Adreno, a- b- 228–231 345, 361, 376, 384, 391–395, 507 Androgen, 26–28, 37, 40–41, 111, SDS. See Sodium dodecyl sulphate 133–134, 168, 460, 468–469 SDS-PAGE, 202, 258–260, 271–272, 285 DNA, 490–491 Selective androgen receptor modulators Erythropoietin, 254, 260 (SARMs), 42, 108, 110–114, 117–120, 156 540 Index

Selective ion monitoring (SIM), 80, Tetrahydrogestrinone (THG), 10, 104, 117, 171–175, 395 157, 162, 401, 522 Septal hypertrophy, 419, 426 Theobromine, 369, 378, 382 Sequence analysis, 320–321 Therapeutic use exemption, 13, 222, 237, 520 Sex-hormone binding globulin (SHBG), THG. See Tetrahydrogestrinone 584 47–51 Threshold, 39, 54, 70, 84, 129, 133, 149, SHBG. See Sex-hormone binding globulin 232, 239, 243, 265, 308, 319, 338, 369, Sialylation, 258 380, 385, 437, 500, 517 Side effects 109, 112, 133, 164, 178, 416, Thrombin, 438, 586 445, 459–478, 494–495, 501 Thromboembolic disease, 435 SIM. See Selective ion monitoring Thrombosis, 257, 413, 435, 465 Sodium dodecyl sulphate (SDS), 202, 271 Thromboxane A2 (TXA2) receptors, 436, 439 Solid-phase extraction (SPE), 80, 220, 240, Thyreostatics, 361, 590 273, 334, 376, 399 TMS, See Derivatization, Stanozolol, 4, 100, 104, 108, 115, 130, 157, trimethylsilylation 161, 399, 437, 464, 470 Transgene, 487 Stenbolone, 104 Trenbolone, 104, 114, 157, 162, 355, 384, Stereoisomers, 234 393, 469, 476 Steroid binding 48, 111 TXA2. See Thromboxane A2 receptors Steroidogenic enzymes, 31, 462 Steroids U endogenous, 25–54, 77–93 UGT2B17, See Uridine exogenous, 99–120, 155–182 diphosphoglucuronosyl transferase profiles, 6, 70, 84, 90, 141, 341, 393 Ultrafiltration, 267 Stimulants, 5, 227, 332, 444, 514 Ultrasonic videodensitometry, 423 Streptavidin conjugated horseradish Uridine-50-diphosphoglucuronosyl- peroxidase, 268 transferase (UDPGA), 52, 66 Sulphate conjugation. See Sulphonation Uridine diphosphoglucuronosyl transferase Sulphonation, 65–73 (UGT2B17), 54, 67, 82, 338 Sulphotransferase (SULTs), 69, 72 Urinary proteases, 267 Supplements, See Nutritional supplements Supraphysiologic doses, 45, 415, 421, 431, V 445 Vasodilatation, 432 Sustanon, 422 Ventricular relaxation 426 Sympathomimetic, 16, 230, 238 VO2 max, 190, 263, 417, 423

T W Tandem mass spectrometry (MS–MS), 9, WAADS, See World Association of 80, 114, 174, 201, 218, 347 Anti-Doping Scientists Testicular atrophy, 46, 471 WADA. See World Anti-Doping Agency Testis, 30–35, 42–45, 68, 471 Western blotting, 268 Testosterone (T), 5, 25–54, 66, 77–92, World Anti-Doping Agency (WADA), 13, 160, 338, 357, 384, 427, 461–464, 117, 129, 155, 191, 228, 263, 268, 328, 468–470 371, 487, 515–524 glucuronide, 53, 66, 81 World Association of Anti-Doping Testosterone to epitestosterone (T/E ratio, Scientists (WAADS), 14 T/E value), 30, 51, 70, 79, 82–84, 159, 338, 523 Z 1-Testosterone, 104, 157, 178, 359 Zeranol, 355, 358