Marijuana and the Cannabinoids F O R E N S I C S C I E N C E M E D I C I N E AND Steven B. Karch, MD, SERIES EDITOR HERBAL PRODUCTS: TOXICOLOGY AND CLINICAL PHARMACOLOGY, SECOND EDITION, edited by Richard L. Kingston and Timothy S. Tracy, 2007 CRIMINAL POISONING: INVESTIGATIONAL GUIDE FOR LAW ENFORCEMENT, TOXICOLOGISTS, FORENSIC SCIENTISTS, AND ATTORNEYS, SECOND EDITION, by John H. Trestrail, III, 2007 FORENSIC PATHOLOGY OF TRAUMA: COMMON PROBLEMS FOR THE PATHOLOGIST, by Michael J. Shkrum and David A. Ramsay, 2007 MARIJUANA AND THE CANNABINOIDS, edited by Mahmoud A. ElSohly, 2006 SUDDEN DEATHS IN CUSTODY, edited by Darrell L. Ross and Theodore C. Chan, 2006 THE FORENSIC LABORATORY HANDBOOK: PROCEDURES AND PRACTICE, edited by Ashraf Mozayani and Carla Noziglia, 2006 DRUGS OF ABUSE: BODY FLUID TESTING, edited by Raphael C. Wong and Harley Y. Tse, 2005 A PHYSICIAN’S GUIDE TO CLINICAL FORENSIC MEDICINE: SECOND EDITION, edited by Margaret M. Stark, 2005 Hampapartiet FORENSIC MEDICINE OF THE LOWER EXTREMITY: HUMAN IDENTIFICATION AND TRAUMA ANALYSIS OF THE THIGH, LEG, AND FOOT, by Jeremy Rich, Dorothy E. Dean, and Robert H. Powers, 2005 FORENSIC AND CLINICAL APPLICATIONS OF SOLID PHASE EXTRACTION, by Michael J.Telepchak, Thomas F. August, and Glynn Chaney, 2004 HANDBOOK OF DRUG INTERACTIONS: A CLINICAL AND FORENSIC GUIDE, edited by Ashraf Mozayani and Lionel P. Raymon, 2004 DIETARY SUPPLEMENTS: TOXICOLOGY AND CLINICAL PHARMACOLOGY, edited by Melanie Johns Cupp and Timothy S. Tracy, 2003 BUPRENORPHINE THERAPY OF OPIATE ADDICTION, edited by Pascal Kintz and Pierre Marquet, 2002 BENZODIAZEPINES AND GHB: DETECTION AND PHARMACOLOGY, edited by Salvatore J.Salamone, 2002 ON-SITE DRUG TESTING, edited by Amanda J. Jenkins and Bruce A. Goldberger, 2001 BRAIN IMAGING IN SUBSTANCE ABUSE: RESEARCH, CLINICAL, AND FORENSIC APPLICATIONS, edited by Marc J. Kaufman, 2001 TOXICOLOGY AND CLINICAL PHARMACOLOGY OF HERBAL PRODUCTS, edited by Melanie Johns Cupp, 2000 CRIMINAL POISONING: INVESTIGATIONAL GUIDE FOR LAW ENFORCEMENT, TOXICOLOGISTS, FORENSIC SCIENTISTS, AND ATTORNEYS, by John H. Trestrail, III, 2000 M ARIJUANA AND C THE ANNABINOIDS Edited by Mahmoud A. ElSohly, PhD The School of Pharmacy, The University of Mississippi; ElSohly Laboratories Inc., Oxford, MS © 2007 Humana Press Inc. 999 Riverview Drive, Suite 208 Totowa, New Jersey 07512 www.humanapress.com All rights 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, microfilming, recording, or otherwise without written permission from the Publisher. The content and opinions expressed in this book are the sole work of the authors and editors, who have warranted due diligence in the creation and issuance of their work. The publisher, editors, and authors are not responsible for errors or omissions or for any consequences arising from the information or opinions presented in this book and make no warranty, express or implied, with respect to its contents. Due diligence has been taken by the publishers, editors, and authors of this book to assure the accuracy of the information published and to describe generally accepted practices. The contributors herein have carefully checked to ensure that the drug selections and dosages set forth in this text are accurate and in accord with the standards accepted at the time of publication. Notwithstanding, as new research, changes in government regulations, and knowledge from clinical experience relating to drug therapy and drug reactions constantly occurs, the reader is advised to check the product information provided by the manufacturer of each drug for any change in dosages or for additional warnings and contraindications. This is of utmost importance when the recommended drug herein is a new or infrequently used drug. It is the responsibility of the treating physician to determine dosages and treatment strategies for individual patients. Further it is the responsibility of the health care provider to ascertain the Food and Drug Administration status of each drug or device used in their clinical practice. The publisher, editors, and authors are not responsible for errors or omissions or for any consequences from the application of the information presented in this book and make no warranty, express or implied, with respect to the contents in this publication. Production Editor: Melissa Caravella Cover design by Patricia F. Cleary Cover Illustration: Medical Cannabis cultivar (Fig. 1, Chapter 1; see complete caption on p. 3). 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The fee code for users of the Transactional Reporting Service is: [978-1-58829-456-2 • 1-58829-456-0/07 $30.00]. Printed in the United States of America. 10 9 8 7 6 5 4 3 2 1 eIBSN 1- 59259-947-8 Library of Congress Cataloging-in-Publication Data Marijuana and the cannabinoids / edited by Mahmoud A. ElSohly. p. ; cm. -- (Forensic science and medicine) Includes bibliographical references and index. ISBN 1-58829-456-0 (alk. paper) 1. Cannabinoids. I. ElSohly, Mahmoud A. II. Series. [DNLM: 1. Cannabinoids. 2. Cannabis. QV 77.7 M33515 2006] QP801.C27M355 2006 615'.7827--dc22 2006012285 Preface Although primarily used today as one of the most prevalent illicit leisure drugs, the use of Cannabis sativa L., commonly referred to as marijuana, for medicinal purposes has been reported for more than 5000 years. Marijuana use has been shown to create numerous health problems, and, consequently, the expanding use beyond medical purposes into recreational use (abuse) resulted in control of the drug through international treaties. Much research has been carried out over the past few decades following the identification of the chemical structure of THC in 1964. The purpose of Marijuana and the Cannabinoids is to present in a single volume the comprehensive knowledge and experience of renowned researchers and scientists. Each chapter is written independently by an expert in his/her field of endeavor, ranging from the botany, the constituents, the chemistry and pharmacokinetics, the effects and consequences of illicit use on the human body, to the therapeutic potential of the cannabinoids. Mahmoud A. ElSohly, PhD v Contents Preface ................................................................................................................ v Contributors ...................................................................................................... ix CHAPTER 1 Cannabis and Natural Cannabis Medicines Robert C. Clarke and David P. Watson ................................................................1 CHAPTER 2 Chemistry and Analysis of Phytocannabinoids and Other Cannabis Constituents Rudolf Brenneisen................................................................................................17 CHAPTER 3 Chemical Fingerprinting of Cannabis as a Means of Source Identification Mahmoud A. ElSohly, Donald F. Stanford, and Timothy P. Murphy ..............................................................................51 CHAPTER 4 Marijuana Smoke Condensate: Chemistry and Pharmacology Hala N. ElSohly and Mahmoud A. ElSohly ......................................................67 CHAPTER 5 Pharmacology of Cannabinoids Lionel P. Raymon and H. Chip Walls ................................................................97 CHAPTER 6 The Endocannabinoid System and the Therapeutic Potential of Cannabinoids Billy R. Martin ....................................................................................................125 viii Contents CHAPTER 7 Immunoassays for the Detection of Cannabis Abuse: Technologies, Development Strategies, and Multilevel Applications vii Jane S-C. Tsai.....................................................................................................145 CHAPTER 8 Mass Spectrometric Methods for Determination of Cannabinoids in Physiological Specimens Rodger L. Foltz ...................................................................................................179 CHAPTER 9 Human Cannabinoid Pharmacokinetics and Interpretation of Cannabinoid Concentrations in Biological Fluids and Tissues Marilyn A. Huestis and Michael L. Smith .......................................................205 CHAPTER 10 Medical and Health Consequences of Marijuana Jag H. Khalsa .....................................................................................................237 CHAPTER 11 Effects of Marijuana on the Lung and Immune Defenses Donald P. Tashkin and Michael D. Roth .........................................................253 CHAPTER 12 Marijuana and Driving Impairment Barry K. Logan ...................................................................................................277 CHAPTER 13 Postmortem Considerations Steven B. Karch ..................................................................................................295 CHAPTER 14 Cannabinoid Effects on Biopsychological, Neuropsychiatric, and Neurological Processes Richard E. Musty................................................................................................303 Index...........................................................................................................................317