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1、HANDBOOK OF FORENSIC DRUG ANALYSISHANDBOOK OF FORENSIC DRUG ANALYSISEditor: Frederick P. Smith, Ph.D.With contributions by: Sotiris A. Athanaselis, Ph.D. Maciej J. Bogusz, M.D., Dr. Sc. John T. Cody, Ph.D., D-FTCBJohn Hugel David A. Kidwell David C. Lankin, Ph.D.John Mario John A. MeyersRobert B. Pa

2、lmer, Ph.D., DABAT Charles Tindall, Ph.D., DABC Jane S.-C. Tsai, Ph.D., FACBSeries Editor: Jay A. SiegelAmsterdam Boston Heidelberg London New York Oxford Paris San Diego San Frsco Singapore Sydney TokyoAcquisitions EditorMark ListewnikProject ManagerSarah HajdukAssociate Acquisitions EditorJennifer

3、 SoucyDevelopmental EditorPamela ChesterMarketing ManagerChristian Nolin Cover Design HannusCompositionSNP Best-SetPrinterThe Maple-Vail Book Manufacturing Group Elsevier Academic Press30 Corporate Drive, Suite 400, Burlington, MA 01803, USA525 B Street, Suite 1900, San Diego, California 92101-4495,

4、 USA 84 Theobalds Road, London WC1X 8RR, UKThis book is printed on acid-paper.Copyright 2005, Elsevier Inc. .No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval sy

5、stem, without permission in writing from the publisher.Permissions may be sought directly from Elseviers Science & Technology Rights Department in Oxford, UK: phone: (+44) 1865 843830, fax: (+44) 1865 853333,:permissions.uk. You may also complete your request on-line via the Elsevier homepage (), by

6、 selecting “Customer Support” andthen “Obtaining Permissions.”Library of Congress Cataloging-in-Publication DataAPPLICATION SUBMITTEDBritish Library Cataloguing in Publication DataA catalogue record for this book is available from the British Library ISBN: 0-12-650641-8For all information on all Els

7、evier/Academic Press publicationsvisit our Web site at or .Printed in the United States of America040506070887654321Acquisitions EditorMark ListewnikProject ManagerSarah HajdukAssociate Acquisitions EditorJennifer SoucyDevelopmental EditorPamela ChesterMarketing ManagerChristian Nolin Cover Design H

8、annusCompositionSNP Best-SetPrinterThe Maple-Vail Book Manufacturing Group Elsevier Academic Press30 Corporate Drive, Suite 400, Burlington, MA 01803, USA525 B Street, Suite 1900, San Diego, California 92101-4495, USA 84 Theobalds Road, London WC1X 8RR, UKThis book is printed on acid-paper.Copyright

9、 2005, Elsevier Inc. .No part of this publication may be reproduced or transmitted in any form or by any means, electronic or mechanical, including photocopy, recording, or any information storage and retrieval system, without permission in writing from the publisher.Permissions may be sought direct

10、ly from Elseviers Science & Technology Rights Department in Oxford, UK: phone: (+44) 1865 843830, fax: (+44) 1865 853333,:permissions.uk. You may also complete your request on-line via the Elsevier homepage (), by selecting “Customer Support” andthen “Obtaining Permissions.”Library of Congress Catal

11、oging-in-Publication DataAPPLICATION SUBMITTEDBritish Library Cataloguing in Publication DataA catalogue record for this book is available from the British Library ISBN: 0-12-650641-8For all information on all Elsevier/Academic Press publicationsvisit our Web site at or .Printed in the United States

12、 of America040506070887654321CONTENTS FOREWORDixPREFACExiABOUT THE AUTHORSxviCHAPTER 1OVERVIEW OF FORENSIC DRUG ANALYSIS1.1 Drug Classifications11.2 Collection of Evidence in Drug Cases (Documentation,Safety, Packaging, Custody)21.3 Laboratory Capabilities and Accreditation4Definition of Terms9Refer

13、ence12CHAPTER 2IMMUNOASSAY TECHNOLOGIES FOR DRUGS-OF-ABUSE TESTING2.1 Introduction132.2 Radioimmunoassay (RIA)172.3 Enzyme Immunoassay (EMIT, ELISA, CEDIA, and other EIAs)182.4 Fluorescence Polarization Immunoassay (FPIA)242.5 Kinetic Interaction of Microparticles in Solution (KIMS)262.6 Onsite (Poi

14、nt-of-Collection) Immunoassays282.7 Performance Characteristics and Quality Managementof Immunoassays312.8 Summary34References34CHAPTER 33.1 Qualitative Seized-Drug Analysis of , Hash, andHash Oil: Current and Historical Perspectives443.2 ProfilingProvenance643.3 Immunoassays for the Detection of Ca

15、nnabinoids inBiological Matrices803.4 Confirmation (Confirmatory Test) of Cannabinoids in Urine Specimens98References130vi CONTENTS CHAPTER 4ANALYSIS OF THE HALLUCINOGENSPART I: INFRARED (IR) SPECTROSCOPY:1544.0 Theoretical Basis1544.1 Infrared Spectrometer Instrumentation1564.2 Infrared Spectroscop

16、y of Lysergic Acid Diethylamide (LSD)1644.3 Infrared Spectroscopy of Phenylalkylamines1654.4 Infrared Spectroscopy of Phencyclidine and Analogs1684.5 Infrared Spectroscopy of Tryptamines1704.6 Furthering172PART II: MASS SPECTROMETRY:1764.7 Theoretical Basis1764.8 Mass Spectroscopy of Lysergic Acid D

17、iethlyamide (LSD)1864.9 Mass Spectroscopy of Phenylalkylamines1874.10 Mass Spectroscopy of Phencyclidine and Analogs1894.11 Mass Spectroscopy of Tryptamines1914.12 Further ing195Acknowledgment202References202PART III: NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY:2054.13 Theoretical Basis2054.14 The NMR E

18、xperiment2074.15 Phencyclidine and Related Substances2174.16 MDA and Analogs2204.17 Ergot and Other Indole Alkaloids2274.18 Tryptamines229References231CHAPTER 5E: METHODS OF FORENSIC ANALYSIS5.1Introduction5.2Origin of 2365.3Noninstrumental Methods for Detection of 2375.4Trace and Instrumental Analy

19、sis2475.5s270References270CHAPTER 6OPIOIDS: METHODS OF FORENSIC ANALYSIS6.1 Introduction2776.2 Preliminary Methods for Opiate Detection2786.3 Isolation of Opiates from Biosamples2846.4 Papaver Somniferum as a Source of Opiates2906.5 and Associated Illicit Opiate Formulations2966.6 Other Opiate Agoni

20、sts3216.7 Summary340CONTENTS viiAbbreviations341References342CHAPTER 7AMPHETAMINES: METHODS OF FORENSIC ANALYSIS7.1Introduction3577.2Detection3617.3Qualitative Methods of Analysis3627.4Qu tative Methods of Analysis3747.5Comparative Analysis and Profiling4157.6432References433CHAPTER 8ILLICIT DRUG MA

21、NUFACTURE (WITH AN EMPHASIS ON CLANDESTINE METHAMPHETAMINE PRODUCTION): SYNTHETIC METHODS AND LAW ENFORCEMENT CONCERNS8.1Range of Operations in Clandestine Laboratories4538.2Manufacture of Methamphetamine4788.3Law Enforcement5148.4Concluding Remarks532References532INDEX545FOREWORD A glance at the pu

22、blications list of most large publishers indicates that books on the subject of forensic science are flourishing. A recent search of the books for sale on the topic of drug and pharmaceutical analysis at A had 303 entries! Why, then, do the editors of this Handbook of Forensic Drug Analysis believe

23、that another entry in this field is needed? The reason is that there is a gap in the available works on drug analysis: a compensive, ed, up-to-date work aimed at drug chemists and other scientists who needto aa few m important m compThere are literally huof these are legally sanctionUniform Drug Con

24、trol Act coversButif one looks at what drugs show up inafter day all over the world, one finds really only a hannes. The Hand- book of Forensic Drug Analysis covers these few, mosinclude marijuana,mon hallucinogens, and amphetamines. Beyond these drugs, the Handblores the subject of clandestine labo

25、ratories, which are beco United States, especially methamphetamine labs. analyz- ing the drugs and other materials seized from these labs are presented. This also a major chapter on immunoassay technologies applied to illicit drugs. Very few works on drug analysis even mention immunoassay methods, l

26、et alone describe them in drug screenings.The Handbook of Forensic Drug Analysis is not meant for the casual interested in gaining an overview of illicit drugs. This book is for the serious scientist who needs to have the latest companalysis of the most common illicit drugs.x FOREWORD The editor of

27、this volume is Dr. Frederick P. Smith at the University of New Haven, West Haven, Connecticut. Dr. Smith has spent his career in research, publishing, and teaching in the area of forensic drug chemistry and is recog- nized as one of the most qualified U.S. scientists in the field. He has assembled a

28、 veritable whos who of experts in this field to contribute their special insights and knowledge about controlled substances. ers and users of this hand- book will find the most current and comp ensive information available on the subject of the analysis of illicit drugs.Jay Siegel Director, Forensic

29、 and Investigative Sciences Program Indiana University, Purdue University, IndianapolisIndianapolis, IndianaPREF ACE Forensic drug analysts and toxicologists utilize methods and techniques that continue to develop rapidly. To this end, forensic scientists need compen- sive information concerning dru

30、g analysis. Many have found it difficult to find in-depth information on drug analysis in one place. Although the field is con- stantly changing, this book attempts to compile current information on the analysis of illicit drugs, condensed and distilled to provide analytical applica- tions appropria

31、te to diverse needs, in hopes of making this informationily accessible. Of particular value throughout are the authors comments cerning the relative value of the analytical methods for each of the drug classes.I hope this will be useful not only to forensic drug but also to advancedanalysis litigati

32、on, scientists working in methods research and development, technicians employed in drug-testing laboratories, and others whose work requires substWhile many different drugs are subject to abuse,classes. These drugs vary widely in origin, from plant material to semisynthetic plant derivatives to pur

33、ely synthetic drugs. Due to the distinct chemical pro- perties of these drugs, the analytical methods presented in this book provide not only immediately useful solutions to forensic practitioners but also mfor future drug analysis problems as the field evolves. The prevalence of illicit- drug use i

34、n todays society ensures the analysis of these substances a permanent place in modern forensic laboratories.In addition to the major emphasis on methods available for the analysis of the major categories of misused drugs, the rapid growth of methamphetamine synthesis warrants special consideration.

35、Low-cost methods include color (or spot) tests, thin-layer chromatography (TLC), spray visualization methods, and microcrystal tests. Traditional instrumental methods, such as gas chromatog- raphy (GC), GC/mass spectrometry (GC/MS), infrared (IR) spectroscopy, and ultraviolet (UV) spectroscopy, comp

36、rise moderate-cost instrumental techniquesxii PREFACE that often require extraction and, with GC, derivatization. Both low-cost and higher-cost methods of analysis a dressed. The explosive growth in clan- destine drug laboratories worldwide, particularly involving methamphetamine, warrants the exten

37、sive consideration given this topic in a separate chapter (Chapter 8). This is designed to assist law enforcement and forensic drug analysts in the numerous challenges they face dealing with illicit-drug manu- facture. Immunoassay (IA) methods can be applied to solid dosage analysis of controlled su

38、bstances easily, without extensive extraction and purification. For this reason, forensic toxicologists find these methods indispensable for analyz- ing biological specimens for abused drugs.Chapter 2 provides a concise review of immunoassay technology for drugs- of-abuse testing. Starting with hist

39、orical and theoretical background informa- tion, this chapter explains clearly each immunoassay class: radioimmunoassay (RIA), enzyme immunoassay (EIA), enzyme multiplied immunoassay technique (EMIT), enzyme-linked immunosorbent technique (ELISA), fluorescent polarization immunoassay (FPIA), and kin

40、etic interaction of microparticles in solution (KIMS). Onsite (point-of-collection) immunoassays are described next. The final section summarizes the important subject of performance characteristics used for evaluation and quality management.Chapter 3 is an extensively referenced treatise that provi

41、des the scientific underpinning for the history, extraction, derivatization, and determination of cannabinoids. The authors have crime laboratory, academic, and industry expertise with. Their chapter contains a thorough evaluation of the background and auseful discussion of whys,how laboratorynterpr

42、etanalytical results. In their reviewg they comparecurrent field tests for plant material, rproducts. Their complaboratory tests to identify y usingcombinations of wet chemical, microscopic, chromic, and spectro- scopic methods. In addition, they discuss traceresidues on drug-use paraphernalia. The

43、authors cover botanical features, both mmicroscopic. Likewise, the array of cannabinoids specific totions are described in the context of their identification by TLC, quid chromatography (LC), and GC/MS. Test methods are described in h appropriate cautions concerning the strengths and limitations of

44、 analytical results. The chapter includes the recommendations for by professional organizations, including the United Nations Drug Control Program (UNDCP), the Scientific Working Group for Seized DrugPREFACE xiiiAnalysis (SWGDRUG), the International Association of Official Analytical Chemists (AOAC)

45、, and the American Board of Criminalists (ABC), as well as those of senior scientists of national laboratory systems in the United States, Britain, Australia, and Holland. As an additional investigative tool, the authors show how “profiling” cannabinoids could assist law enforcement with tactical in

46、telligence. Specific cannabinoid immunoassays occupy an entire section, where they are compared and evaluated. Separately, DNA ty ofis described as a novel, nonchromatographic approach. While unscope, this chapter provides the depth requisite to understanding di fromChapter 4, on hallucinogens, prov

47、ides a different and very useful approto forensic drug analysis. The authors explain the theory and practical appli- cation of major instruments, including IR, Fourier transform infrared (FTIR), mass spectrometry, and nuclear magnetic resonance (NMR). While each instrumenthasspecialapplicationstohal

48、lucinogens(lysergic diethylamine/LSD,tryptamines,phencyclidine/PCP,and lamines/MDMA), the authors approach assists the forensic anabackground for the use of these instrumental method Generous use of spectra and related figures clearly ilChapter 5 reviews the forensic analysis ofprevalence transcends

49、 economic boundaries, the authors present a range of analytical approaches. The authors explain simple, low-cost, noninstrumental techniques (i.e., microcrystal tests, spot tests, and thin-layer chromatography). Photomicrographs of the crystal tests provide useful illustrations not available elsewhe

50、re.e-related immunoassays are compared and evalu- ated. A wide range of instrumental techniques are described, including several less commonly employed in a forensic setting as well as those that find wide application, such as gas chromatography with nitrogen-phosphorous detection (GC-NPD), high-per

51、formance liquid chromatography (HPLC), capillary zone electrophoresis (CZE), ion mobility mass spectrometry (IMS), GC/MS, tandem mass spectrometry (MS/MS), IR and Fourier transform infrared spectroscopy (FTIR), Raman infrared spectroscopy, and NMR. The meaningful evaluations presented explain the st

52、rengths and limitations of these tests, thereby enhanc- ing the forensic utility of this chapter.Chapter 6, on opioids analysis, draws on the authors expertise to shed valuable insights on the interpretation of results, including subtleties such as monoacetyl morphine (6-MAM) measurements. First, pr

53、eliminary tests include those suitable for field tests on the street drugs themselves (color tests and immunologically based tests) and individuals who may have consumed them (onsite tests). Concerning other initial or presumptive tests, the screening testxiv PREFACE section presents various opiate-

54、specific immunoassays, common adulterants, and countermeasures laboratories use to defeat adulteration and sample tam- pering. Particularly useful is the practical information devoted to specimen extraction, glucuronide separation, derivatization, and analysis (routinely by GC/MS). The text addresse

55、s efforts to discern opiates consumed inadvertently from foodstuffs such as poppy seed cake. Because the practice of smoking has increased, the inclusion of pyrolysis product research had increased relevance. Specific analytical treatment is given to each major bio- logical fluid (urine, blood, and

56、alternative matrices). The authors discuss therapeutic uses of numerous opioids, including codeine-related drugs, buprenorphine, methadone, tramadol, keto-opioids, fentanyl-related drugs, ketobemidone, butorphanol, and dextromethorphan. Finally, the text critiques methods for comparing (or “profiling”) illicitsamples.Chapter 7, on the analysis of amphetamines, methods in forensic laboratory and onsite testing. T(both instrumental and onsite) and TLC. The texes inherent in saliva, hair, sweat, and meconium analyses,o envi- ronmental exposure.