Forensic Toxicology Controlled Substances and Dangerous Drugs Forensic Toxicology Controlled Substances and Dangerous Drugs

Home , Ambutonium bromide, Benactyzine, Benzquinamide, Biperiden, Butallylonal, Buthalital

W T. Lowry and James C. Garriott Southwestern Institute of Forensic Sciences Dallas, Texas

Plenum Press· New York and London Library of Congress Cataloging in Publication Data Lowry, William Thomas, 1942- Forensic toxicology. Bibliography: p. Includes index. 1. Chemistry, Forensic. 2. Drugs. 3. Narcotics, Control of - United States. 4. Drugs - Laws and legislation - United States. I. Garriott, James C., joint author. II. Title. HV8073.L75 614'.19 78-26439 ISBN-13: 978-1-4684-3446-0 e-ISBN-13: 978-1-4684-3444-6 001: 10.1007/978-1-4684-3444-6

Softcover reprint of the hardcover 1st edition 1979 All righ ts reserved No part of this book may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microftlrning, recording, or otherwise, without written permission from the Publisher Preface

With the rapid spread of drug use and abuse in this country over the last decade, events relating to drugs have become increasingly prominent in the court of law as well as in society in general. It is anticipated that throughout the 1980s this problem will continue to be one of the major social problems in the United States. With the complexity of the Federal and state laws and their interrelationships, and with the increasing demand for the expert chemist or toxicologist, or both, in the courtroom, more education for these people relating to drugs must be implemented. The prosecuting and defense attorneys are also in need of accurate toxicological information to adequately handle cases in which drugs playa role. This book is intended to be a practical as well as an educational book-a resource tool for the active forensic chemist, as well as for the student. It is with the forensic chemist in mind that the material on controlled substances and substances found in cases of drug abuse has been arranged in a systematic order for quick and easy reference. This section includes synonyms, pharma• ceutical preparations, biochemistry and/or pharmacognosy, toxicology and/or pharmacology, and how the substance is controlled under Federal law. Under the concept of scientific consideration as compared with the Federal law, this book enables one to deal with some of the major conflicts in the American legal system concerning scientific evidence and how it is presented in a court of law. The first section of the book discusses the concept of drugs and specifica• tions that pharmaceutical companies must meet and maintain to market a new product. The next section deals with the Federal Controlled Substances Act, including requirements for registration of controlled substances, and the rules and regulations under which a forensic laboratory must handle drug evidence relating to testing. Among the topics discussed are security requirements, including recommendations presented by the Drug Enforcement Admin• istration for handling drug evidence obtained from police seizures, labeling and packaging requirements for controlled substances, record-handling for v vi PREFACE controlled substances, inventory requirements, prescriptions, and statement of the Act itself, listing drugs included in Schedules I, II, III, IV, and V. Brief discussions on adulterated and misbranded drugs, as well as illicit preparations and their legal status, are included. The section describing pharmaceutical dosage forms includes packaging types and formulations such as aerosols, capsules, creams, elixirs, emulsions, extracts, fluid extracts, gels, inhalants, injections, jellies, lotions, ointments, pastes, powders, solutions, spirits, suppositories, suspensions, syrups, tablets, tinctures, and waters. The discussion of excluded and excepted substances under the Controlled Substances Act provides a systematic protocol for handling pharmaceutical preparations encountered in the laboratory, especially when extrapolating Federal law to state laws. Specific exceptions are listed and described. The discussion termed" dangerous drugs" deals with a broad range of regulations outside the Controlled Substances Act. These include legend drugs, banned drugs, and nonapproved new drugs undergoing clinical trial. Certain over-the-counter drugs, or nonprescription drugs, are listed if they are frequently found in cases of drug abuse or encountered in excepted and excluded substances. The final section of the text provides an alphabetical listing of all substances listed in the Controlled Substances Act, and other selected dangerous drugs and nonprescription drugs. Each substance is listed by generic name. A listing of other generic names and IUPAC names under the heading" Synonyms" provides the reader with a quick reference to the drug. Included with each substance is a listing of its common trade names and its formulations containing the titled drug. If the pharmaceutical preparation causes deviation of control due to its formulation, it is so stated. Also included for each substance is a discussion of the biochemistry and/or pharmacognosy, and of the toxicology-pharmacology of that substance. Basically, all information discussed is intended to include the necessary material to provide the scientific expert with information to testify in a court of law; to provide the attorneys with enough information to assist in prosecuting or defending a drug case; and to provide physicians with information on drugs and drug laws to assist in maintaining proper records and prescription practices. Under no circumstances do the authors of this book intend for this to be a legal document. All subject matter is based on legal documents with certain opinions of the authors found throughout. In general, this book should give the reader an overall working knowledge of how to apply state and Federal laws, how to interrelate these laws, and how to interpret them scientifically when called upon to do so. It is the intent of the authors to bridge the gap between scientific and legal investigations in the fields of controlled substances and dangerous drugs. PREFACE vii

We wish to acknowledge some special people who were diligent in their efforts during the preparation of this manuscript. Thanks go to Mrs. Karen Partain, Mrs. Aileen Langston, Mrs. Jan Laird, Miss Laura Seaman, and Mrs. Terri Austin. Also, we are grateful to Mr. Frank Jackson, Criminal Defense Attorney, Dallas, Texas and Mr. Jim Barklow, Chief Felony Prosecutor, Office of the District Attorney, Dallas County, Texas, for the time they gave in consultation on legal matters set forth in this book. We are also indebted to the staff of Plenum Publishing Corporation for continuous and skillful advisement during the final stages of preparation of the manuscript. Special appreciation goes to Ms. Nancy Mester, Senior Production Editor, for her patience with us when we failed to meet deadlines.

W. T. Lowry J. C. Garriott

Dallas Contents

List of Controlled and Noncontrolled but Commonly Abused Substances xii

1. Introduction 1 New Drugs 2 Advertising 4 Adulterated Drugs 4 Misbranded Drugs 5 Drug Nomenclature 6

2. Pharmaceutical Dosage Forms 9 Aerosols 9 Capsules 10 Creams. 11 Elixirs . 11 Emulsions . 11 Extracts 11 Gels and Magmas 12 Inhalations 12 Injections 12 Powders 13 Solutions 14 Spirits . 14 Suppositories 14 Suspensions 15 Syrups. 15 Tablets. 15 Tinctures 16 be x CONTENTS

3. Classification of Scheduled Substances 17 Schedules. 17 Fraudulent Offenses . 20 Commercial Offenses. 21 Prescription of Nonscheduled Drugs 21

4. Regulation of Controlled Substances. 23 Requirements for Registration 23 Applications for Registration 26 Application Forms 27 Modification, Transfer, and Termination of Registration 28 Security Requirements . 33 Labeling and Packaging Requirements for Controlled Substances. 35 Records and Reports of Registrants 38 Inventory Requirements. 42 Continuing Records 44 Order Forms . 45 Prescriptions . 53 Controlled Substances Listed in Schedule II 55 Controlled Substances Listed in Schedules III and IV 57 Controlled Substances Listed in Schedule V . 59

5. Excluded Substances . 63 Exclusion from a Schedule 63 Excluded Substances. 63

6. Excepted Substances . 67 Requirements for Exception 67 Excepted Substances. 68 Allobarbital Preparations 68 Amobarbital Preparations . 68 Amphetamine Preparations 69 Aprobarbital Preparations (None Excepted). 69 Barbital Preparations . 69 Butabarbital Preparations . 69 Butalbital Preparations. 71 Butallylonal Preparations (None Excepted) 71 Buthalital Preparations (None Excepted) 71 Butobarbital Preparations (None Excepted) . 71 CONTENTS xi

Chloral Betaine Preparations (None Excepted) 71 Chlordiazepoxide Preparations 71 Clonazepam Preparations (None Excepted) . 71 Clorazepate Preparations (None Excepted) . 71 Cyclobarbital Preparations (None Excepted) 72 Cyclopentylallylbarbituric Acid Preparations 72 Diazepam Preparations (None Excepted) 72 Ethclorvynol Preparations (None Excepted) . 72 Ethinamate Preparations (None Excepted) . 72 Flurazepam Preparations (None Excepted) . 72 Glutethimide Preparations (None Excepted). 72 Heptobarbital Preparations (None Excepted) 72 Hexobarbital Preparations (None Excepted). 72 Ibomal Preparations (None Excepted) 72 Lysergic Acid Preparations (None Excepted) 72 Lysergic Acid Amide Preparations (None Excepted) 72 Mebutamate Preparations (None Excepted) . 72 Meprobamate Preparations 72 Methamphetamine Preparations (None Excepted) 73 Methaqualone Preparations (None Excepted) 73 Metharbital Preparations (None Excepted) . 73 Methohexital Preparations (None Excepted). 73 Methylphenidate Preparations (None Excepted) 73 Mephobarbital Preparations . 73 Methyprylon Preparations (None Excepted). 73 Narcobarbital Preparations (None Excepted) 73 Nealbarbital Preparations (None Excepted) . 74 Oxazepam Preparations (None Excepted) 74 Paraldehyde Preparations (None Excepted) 74 Pentobarbital Preparations. 74 Petrichloral Preparations (None Excepted) 75 Phencyclidine Preparations (None Excepted) 75 Phenmetrazine Preparations (None Excepted) 75 Phenobarbital Preparations 75 Probarbital Preparations (None Excepted) . 89 Secobarbital Preparations . 89 Sulfodiethylmethane Preparations (None Excepted) 89 Sulfonethylmethane Preparations (None Excepted) . 89 Sulfonmethane Preparations (None Excepted) 89 Thialbarbital Preparations (None Excepted) . 90 Thiamylal Preparations (None Excepted) 90 Thiopental Preparations (None Excepted) 90 Vinbarbital Preparations (None Excepted) 90 xii CONTENTS

7. Drug Isomers and Derivatives 91 Schedule I 91 Schedule II 94 Schedule III 95 Schedule IV 95 Schedule V 96 Optical Isomers 97 Geometrical Isomers. 98 Positional Isomers 99 Esters 99 Ethers 100 Salts 100

8. Techniques and Instrumentation for Analysis of Drugs. 103 Chromatography: Thin-Layer, Paper, and Column 103 Ultraviolet and Visible Spectrophotometry 105 Infrared Spectrophotometry. 106 Spectrofluorimetry 106 Gas Chromatography 107 Gas Chromatography-Mass Spectrometry (GC-MS) 109 Liquid Chromatography 110 Radioimmunoassay . 110 EMIT, HI, and FRAT . III Nuclear Magnetic Resonance (NMR) Spectroscopy. 112

9. Controlled and Noncontrolled but Commonly Abused Substances. 117 Acepromazine . 117 Aminophylline 127 Acetaminophen. 1I8 Amitriptyline 128 Acetanilide . I 18 Amobarbital 130 Acetophenazine. 1I9 Amphetamine 132 Acetorphine. 120 Amyl Nitrite 134 Acetyldihydrocodeine 121 Anhalonidine 135 Acetylmethadol . 121 Anhalonine. 136 Aletamine 122 Anileridine . 136 Allobarbital. 123 Anisotropine 137 Allylprodine 123 Apomorphine 137 Alphaacetylmethadol 124 Aprobarbital 138 Alphameprodine 124 Ascorbic Acid 138 Alphamethadol . 124 Atropine. 139 Alphaprodine 125 Azacyclonol. 140 Ambutonium Bromide. 126 Barbital. 140 CONTENTS xiii

Benactyzine . 141 Cocaine . 171 Benzethidine 142 Codeine. 173 Benzitramide 142 Codeine Methylbromide 177 Benzocaine 143 Codeine-N-oxide 177 Benzphetamine 143 4-Cyano-2-dimethylamino- Benzquinamide . 144 4,4-diphenyl Butane . 178 Benzylmorphine 145 4-Cyano-l-methyl- Betaacetylmethadol 146 4-phenylpiperidine 178 Betameprodine 146 Cyclobarbital 179 Betamethadol 146 Cyclopentenylallylbarbituric Betaprodine . 146 Acid 180 Biperiden 147 Cyprenorphine . 180 4-Bromo-2,5-dimethoxy- Cyproheptadine 181 amphetamine. 147 Desipramine. 182 Bufotenine 148 Desomorphine 183 Butabarbital 149 Dextromethorphan . 183 Butalbital 150 Dextromoramide 184 Butallylonal . 151 Dextrorphan 185 Butaperazine 152 Diampromide 185 Buthalital 153 Diazepam 185 Butobarbital. 153 Dicyclomine 187 Caffeine. 154 Diethylpropion . 188 Captodiame . 154 Diethylthiambutene 189 Carbromal 155 Diethyltryptamine 190 Carisoprodol 155 Difenoxin 190 Carphenazine 156 Dihydrocodeine 191 Chloral Betaine. 157 Dihydrocodeinone Chloral Hydrate 157 (Hydrocodone) 192 Chlordiazepoxide 158 Dihydroergotamine 194 Chlorhexadol 160 Dihydroergotoxine . 194 Chlormezanone. 160 Dihydromorphine 195 Chlorpheniramine 161 Dimenoxadol 195 Chlorphentermine 162 Dimepheptanol . 196 Chlorpromazine 162 Dimethocaine 196 Chlorprothixene 164 2,5-Dimethoxyamphetamine 197 Chlorzoxazone 165 2,5-Dimethoxy- Clonazepam . 166 4-methylamphetamine 197 Clonitazene . 167 Dimethylthiambutene 198 Clopenthixol 168 Dimethyltryptamine 199 Clorazepate . 168 Dioxaphetyl Butyrate 200 Clortermine . 169 Diphemanil Methylsulfate . 200 Coca. 170 Di phenhydramine 201 xiv CONTENTS

Diphenoxylate 201 Haloperidol . 232 Dipipanone . 203 Harmine. 233 Dipropyltryptamine 203 Heptabarbital 234 Doxapram 204 Heroin 234 Doxepin. 205 Hexobarbital 236 Droperidol 206 Hexocyc1ium Methylsulfate 237 Drotebanol 207 Homatropine 238 Dyphylline 207 Hydrocodone 239 Ecgonine. 208 Hydromorphinol 239 Emy1camate . 208 Hydromorphone 240 Ephedrine 209 6-Hydroxydimethyltryptamine 241 Ergonovine 210 7-Hydroxydimethyltryptamine 241 Ergotamine 211 Hydroxypethidine 241 Ergotoxine 212 Hydroxyphenamate 242 Estrogens (Conjugated) 213 Hydroxyzine. 242 Ethaverine 213 Hyoscine 244 Ethchlorvynol 214 Hyoscyamine 245 Ethinamate . 215 Ibogaine. 245 Ethoheptazine 216 Ibomal 246 Ethomoxane. 216 Imipramine 247 Ethylmethylthiambutene 217 Isomethadone 249 Ethylmorphine . 217 Isosorbide Dinitrate 250 Ethyl-4-phenylpiperidine- Ketobemidone 251 4-carboxylate . 218 Lactose 251 N- Ethyl-3-piperidyl Benzilate . 219 Levomethorphan 252 Etonitazene . 219 Levomoramide . 252 Etorphine 220 Levophenacylmorphan . 253 Etoxeridine . 221 Levorphanol 253 Fencamfamin 221 Lidocaine 254 Fenethylline . 221 Lorazepam 255 Fenfluramine 222 Lysergic Acid 256 Fenimide. 223 Lysergic Acid Amide 256 Fenpipramide 223 Lysergic Acid Diethylamide 257 Fenpiprane 224 Mannitol Hexanitrate 259 Fentanyl. 224 Marijuana 259 Fluanisone 225 Mazindol 266 Fluopromazine 225 Mebutamate 267 Fluphenazine 226 Mec1oqualone 268 Flurazepam . 227 Mephentermine . 269 Furethidine . 229 Mephobarbital 269 Glutethimide 229 Meprobamate 270 Glycopyrrolate 231 Meprodine 272 CONTENTS xv

Mescaline 273 Morphine 302 Metazocine 275 Morphine Methylbromide . 305 Methadol 275 Morphine Methylsulfonate 305 Methadone 276 Morphine N-Oxide . 306 Methamphetamine . 278 Myrophine 306 Methapyrilene 280 Nalorphine . 307 Methaqualone. 281 Narcobarbital 308 Metharbital . 282 Nealbarbital. 308 Methenamine 283 Nicocodeine . 309 Methocarbamol 283 Nicomorphine 309 Methohexital 284 Nikethamide 310 Methotrimeprazine . 285 Nitrazepam . 310 Methoxamine 286 Nitroglycerin 312 4-Methoxyam phetamine 287 Noracymethadol 313 5-Methoxydimethyltryptamine 288 Norlevorphanol. 313 5-Methoxy-3,4-methylene- Normethadone 314 dioxyamphetamine 288 Normorphine 314 Methoxyphenamine 289 Norpipanone 315 p-Methoxyphenethylamine. 289 Norpseudoephedrine 315 Methoxypromazine. 290 Opium 316 5-Methoxytryptamine 290 Oxazepam 323 Methscopolamine 291 Oxycodone 324 Methyldesorphine 291 Oxymorphone 325 Methyldihydromorphine 292 Oxypertine 326 3,4-Methylene- Oxyphencyclimine 326 dioxyamphetamine 292 Papaverine 327 Methylergometrine . 293 Paraldehyde. 327 2-Methyl-3-morpholine- Pecazine . 328 1,I-diphenylpropane Pemoline. 329 Carboxylic Acid . 294 Pentaerythritol Tetranitrate 329 Methylphenidate 294 Pentazocine . 330 I-Methyl-4-phenylpiperidine- Penthienate Bromide 331 4-carboxylic Acid 295 Pentobarbital 332 N-Methyl-3-piperidylbenzilate 296 Pericyazine 334 Methyltestosterone. 297 Perphenazine 335 Ct-Methyltryptamine 298 Pethidine. 336 N-Methyltryptamine 298 Peyote 338 Methyprylon 299 Phenacetin 339 Methysergide 300 Phenadoxone 340 Metopon 300 Phenampromide 340 Moramide 301 Phenazocine. 341 Morpheridine 302 Phenazopyridine 342 xvi CONTENTS

Phencyclidine 342 Protokylol 371 Phendimetrazine 343 Pseudoephedrine 372 Phenelzine 344 Psilocin 372 Pheniramine . 345 Psilocybin 373 Phenmetrazine 346 Quinidine 374 Phenobarbital 347 Quinine. 375 Phenomorphan . 349 Racephedrine 376 Phenoperidine 349 Racemethorphan 376 Phenprobamate . 350 Racemoramide 377 Phentermine . 350 Racemorphan 377 1-Phenylcyclohexylamine 351 Rescinnamine 378 Phenylephrine 351 Reserpine 378 Phenylpropanolamine . 352 Salicylate 381 Phenylpropylmethylamine . 352 Scopolamine. 382 Phenytoin 352 Secobarbital. 383 Pholcodine 354 Sodium Nitrite 385 Piminodine 355 Sulfondiethylmethane 386 Pipamperone 355 Sulfonethylmethane 386 Pipenzolate Bromide 356 Sulfonmethane . 387 I-Piperidinocyclohexane- Tetrahydrocannabinol. 387 carbonitrile 356 Thebacon 389 Piperidolate Bromide 357 Thebaine 389 Pipethanate 357 Theobromine 390 Pipradrol 358 Theophylline 391 Piritramide 358 Thialbarbital 392 Poldine Methylsulfate 359 Thiamylal 393 Prazepam 360 1-[1-(2-Thienyl)-cyclohexyl]- Probanthine . 360 piperidine. 395 Pro barbital 361 Thiopental 395 Procaine. 361 Thiopropazate 398 Prochlorperazine 363 Thioproperazine 398 Proheptazine 364 Thioridazine 399 Prolintane 364 Thiothixene . 400 Promazine 365 Thiphenamil 401 Promethazine 365 Tocamphyl 401 Promethestrol Dipropionate 366 Tranylcypromine 401 Properidine . 366 Tricyclamol . 403 Propiomazine 367 Tridihexethyl Chloride. 404 Pro pi ram 367 Trifluoperazine . 404 Propoxyphene 368 Triflupromazine 405 Propylhexedrine 370 Trihexyphenidyl 406 Prothipendyl 371 Trimeperidine 406 CONTENTS xvii

Trimeprazine 407 Tybamate 408 3,4,5-Trimethoxyamphetamine 407 Vinbarbital 409 Trolnitrate . 408 Yohimbine 410

Bibliography and References. 411 Bibliography 411 References 412

Index . 421