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A Clinician’s Guide to
Cannabinoid Science
Cannabinoid Science by Steven James tackles the issues surrounding the use of
cannabinoids with a refreshingly objective tone that threads the needle between
advocacy and opposition. Presented in a readable scientific voice, this book
explores the history, the specific compounds, the mechanism of action and the
distinct therapeutic targets of cannabinoids in a concise yet comprehensive
style. Particularly useful are the bullet points at the beginning of each chapter
summarizing chapter composition and the numerous references documenting
the content. Nowhere else will the reader find the breadth of coverage of
cannabinoids under one cover, nor is there any better source for the facts.
This book is a must read both for clinicians wanting information about canna-
binoids for their patients taking them as well as for patients themselves who
want access to the best science available.
Dr Stephen M. Stahl, University of California at San Diego, San Diego, California

In this thoroughly researched, scholarly book, Dr James has drawn on his

extensive experience interpreting clinical trials and his skill as a clinician to
present a cohesive account of cannabinoid science. This is a valuable resource
for anyone wishing to understand the clinical implications of this evolving field.
Dr Wallace Mendelson, expert in psychiatry and sleep medicine
A Clinician’s Guide to
Cannabinoid Science
Steven James
Clinical Assistant Professor of Psychiatry, University of California, San Diego
University Printing House, Cambridge CB2 8BS, United Kingdom
One Liberty Plaza, 20th Floor, New York, NY 10006, USA
477 Williamstown Road, Port Melbourne, VIC 3207, Australia
314–321, 3rd Floor, Plot 3, Splendor Forum, Jasola District Centre, New Delhi – 110025, India
79 Anson Road, #06–04/06, Singapore 079906

Cambridge University Press is part of the University of Cambridge.

It furthers the University’s mission by disseminating knowledge in the pursuit of
education, learning, and research at the highest international levels of excellence.

www.cambridge.org
Information on this title: www.cambridge.org/9781108730754
DOI: 10.1017/9781108583336
© Steven P. James 2021
This publication is in copyright. Subject to statutory exception
and to the provisions of relevant collective licensing agreements,
no reproduction of any part may take place without the written
permission of Cambridge University Press.
First published 2021
Printed in the United Kingdom by TJ International Ltd, Padstow Cornwall
A catalogue record for this publication is available from the British Library.
Library of Congress Cataloging-in-Publication Data
Names: James, Steven (Professor of psychiatry), author.
Title: A clinician's guide to cannabinoid science / Steven James, Clinical Assistant Professor of Psychiatry,
University of California, San Diego.
Description: Cambridge, United Kingdom ; New York, NY : Cambridge University Press, 2021. | Includes
bibliographical references and index.
Identifiers: LCCN 2020026272 (print) | LCCN 2020026273 (ebook) | ISBN 9781108730754 (paperback) |
ISBN 9781108583336 (ebook)
Subjects: LCSH: Cannabinoids. | Cannabinoids – Therapeutic use.
Classification: LCC RM666.C266 J35 2021 (print) | LCC RM666.C266 (ebook) | DDC 615.7/827–dc23
LC record available at https://lccn.loc.gov/2020026272
LC ebook record available at https://lccn.loc.gov/2020026273
ISBN 978-1-108-73075-4 Paperback
Cambridge University Press has no responsibility for the persistence or accuracy of
URLs for external or third-party internet websites referred to in this publication
and does not guarantee that any content on such websites is, or will remain,
accurate or appropriate.
.......................................................................................................................................................
Every effort has been made in preparing this book to provide accurate and up-to-date information that is in
accord with accepted standards and practice at the time of publication. Although case histories are drawn
from actual cases, every effort has been made to disguise the identities of the individuals involved.
Nevertheless, the authors, editors, and publishers can make no warranties that the information contained
herein is totally free from error, not least because clinical standards are constantly changing through
research and regulation. The authors, editors, and publishers therefore disclaim all liability for direct or
consequential damages resulting from the use of material contained in this book. Readers are strongly
advised to pay careful attention to information provided by the manufacturer of any drugs or equipment
that they plan to use.
For Lisa Thank you for your patience over the many long hours.
I am sure you are ready for a long vacation!
Contents
Preface ix

Section 1: An Introduction to Section 2: Potential Therapeutic

Cannabinoid Science Uses of Cannabinoids in Clinical
1 An Introduction to the Botany Practice
and History of Cannabinoids 1
6 Cannabinoids and Pain 70
2 Δ -Tetrahydrocannabinol (THC) and
9
7 Cannabinoids and
Cannabidiol (CBD) 13
Neuropsychiatry 86
3 The Endocannabinoids 27
8 Cannabinoids in Sleep and Circadian
4 Approved Cannabinoid Rhythms 100
Medicines for Therapeutic
9 Cannabinoids and Inflammation
Use 41
and Autoimmune Disorders 113
5 The Safety of Phytocannabinoids
10 Cannabinoids and the Eye 125
and Cannabinoids in Clinical
Practice 55 11 Cannabinoids and the Skin 137

Index 149

vii
Preface
As to diseases make a habit of two things – to help, or at least, to do no harm.
Hippocrates, Of the Epidemics

When I decided to write “The Clinicians Guide to Cannabinoid Science,” I was unsure how
this book would end. Perhaps that is the usual situation when a work of fiction is created by
an author, but this seemed highly irregular in a book about science. Science is, after all,
about data and facts. Over the course of my lifetime I have written, edited or read thousands
of scientific papers and, although there were surprises, generally I could predict how the
paper would end.
At the start of my career, I was immersed in the details of running clinical trials to
develop better treatments for the care of my patients. Soon I became aware of how rapidly
science progresses and the necessity for lifelong learning for myself and both the patient and
the healthcare professional.
Originally, I had little interest in or awareness about marijuana and cannabis. As public
interest and acceptance of cannabis grew, patients and colleagues would ask me questions
that I could not answer. I had formed opinions, but they were based less on my limited
knowledge about the science of cannabinoids and more on my biases. Probably the same is
true for many of my colleagues in the healthcare professions and the general public.
Between 1999 and 2017 approximately 25,000 articles were published in the peer-reviewed
medical journals, yet many textbooks used by clinicians as references to patient care included
little or none of this information. Parallel to this flood of scientific knowledge on cannabinoids
were the social and cultural movements to remove the prohibition of use and improved access.
California was the first state in 1995 to allow the use of marijuana for medical conditions and
the majority of states, Canada, many countries including most in the EU, Latin America,
Australia and New Zealand have followed. Now, over a quarter of a century later, the trend
continues with several countries and US states also legalizing recreational use.
I wrote this book because I could see daily the growing chasm between science and
public opinion on cannabinoids. There is an opportunity to capture the moment and
discover new treatments for devastating, hard-to-treat diseases but only if we are informed
about the science. Hopefully this book will contribute to the scientific knowledge of
clinicians and allow patients and society to be better informed.
When I decided to write this book, I chose to be the sole author. This proved to be a great
challenge to me as I soon learned that cannabinoids touch nearly every aspect of human health.
The endocannabinoid system is not an isolated system of interest to a few researchers but an
immense network that regulates many physiological functions necessary to health.
I could not have written this book without the assistance of cherished colleagues who
advised and corrected me when my knowledge was incomplete or wrong. My support staff
were dedicated professionals and insured things were done well and on time even when
I preferred to pause and reflect on what I had newly learned.
To Stephen Stahl, MD, PhD, my teacher, colleague and friend for nearly 40 years, thank
you for your vision and support to have this book written. Wallace Mendelson, MD, another
teacher and friend of also nearly 40 years, provided me guidance and inspiration to write

ix
x Preface

this book. Without his encouragement this book would never have been attempted. Cristina
Damatarca, MD, another long-term gifted colleague and friend, helped me identify the
important safety issues we find ourselves confronting today with the parallel paths pursued
by medical marijuana and discovery of new medicines from the pharmaceutical and biotech
industries. Myles Jaffe, PhD, another long-term and cherished colleague, advised me on
both the science and reminded me always focus on the truth. His comments were so
insightful that after our discussions I would usually return to my writing with multiple
revisions to every chapter. Renata Kisa, MD, a highly experienced dermatologists and
medical educator, patiently explained to me the fascinating science of the skin. Greg
DeLorenzo, MD, a prominent expert in rheumatology and superb physician, is also
a friend that with his depth of knowledge and gift of communication helped me write the
most difficult of chapters in immunology. I also wish to recognize and thank Robert
Johnson, PhD, a young neuroscientist with knowledge and wisdom beyond his years.
Robert helped me immensely to understand the role of cannabinoids and pain.
I also wish to express my deepest gratitude to Rose Freedland for her beautiful and
inspiring illustrations for the book cover and chapters. I only hope the words I have written
come close to describing what Rose has created. Alissa Williams provided the transcription
of my hard-to-understand dictations and I hope the long chemical names and medical
words were not too much of a burden. And a special thanks to Anya Gorban, a gifted artist
that with eye to detail helped immensely in the final weeks of preparation for this book.
Finally, a special acknowledgment to the incredibly professional and capable team at
Cambridge University Press. Catherine Barnes and Jessica Papworth have been marvelous!
 Section 1 An Introduction to Cannabinoid Science
Chapter
An Introduction to the Botany

1 and History of Cannabinoids

Botany, the eldest daughter of medicine.

Johann Hermann Baas, Outlines of the History of Medicine and the Medical Profession

• Approximately one-fourth of all current prescription medicines are formulations that

are either substances or derivatives of molecules from botanical sources.
• Cannabis sativa, also known as “marijuana,” has been used for thousands of years. In
1964 Δ9-tetrahydrocannabinol (THC) was first isolated and identified as the
psychoactive constituent in the plant.
• In the late 1980s the first cannabinoid receptor that bound THC was discovered in the
brain. Molecules referred to as endocannabinoids that bind to the cannabinoid receptors
and are produced within the body were subsequently identified.
• Two types of cannabinoid receptors have been identified and are named CB1 and CB2.
Cannabinoid receptors are G protein-coupled receptors widely distributed within the
central and peripheral nervous system and multiple regions of the body.
• Phytocannabinoids are three-ring structures synthesized by the cannabis plant.
Endocannabinoids are bioactive fatty acids derived from arachidonic acid in the body.
Both groups bind to cannabinoid receptors.

1
2 Section 1: An Introduction to Cannabinoid Science

Introduction
Plants have been a plentiful source of useful drugs and remedies throughout human history.
In the early nineteenth century Friedrich Sertürner isolated morphine from the opium
plant. By 1827, morphine was marketed by Merck in Germany and the origins of the
modern pharmaceutical industry began. Over the remainder of the nineteenth century
further advances in organic chemistry led to identification of other drugs from plant
material. Examples of important medicines developed from plants included quinine from
the bark of the cinchona tree for the treatment of malaria and salicylic acid from the willow
tree that eventually led to the development of aspirin (Anderson, 2005). Today, the World
Health Organization estimates that over 100 plant species are the source of approved
pharmaceutical products and thousands of other plants are used for medical and recrea-
tional applications (Potter, 2014).
Progress in the identification of the constituents of cannabis (also known as marijuana)
lagged behind the advances in plant chemistry. Although the cannabis plant has been used
for fiber, as a medication, as a source of nutrition and as an element of religious ceremonies
for over 4000 years, the constituents of the plant were extremely difficult to chemically
separate because they were highly lipophilic, water-insoluble and frequently gelatinous.
Isolating the substance that induced the psychoactive effect of cannabis was especially
resistant to exploration (Iversen, 2008). Only in the 1930s was the structure of cannabinol
(CBN) partially isolated by the British chemist Robert Cahn and work by Alexander Todd
and Roger Adams in the 1940s in Britain and the United States came close to identifying
cannabidiol (CBD) (Iversen, 2008). Finally, in 1964 Raphael Mechoulam and Yehiel Gaoni
at Hebrew University separated (-)Δ9-tetrahydrocannabinol (also known as THC), a three-
ring, 21-carbon terpenophenolic structure, from cannabis and demonstrated that the
molecule was responsible for the psychoactive effects (Gaoni and Mechoulam, 1964).
From this discovery followed 25 years of research that identified multiple naturally occur-
ring cannabinoids from plants, referred to as phytocannabinoids and new compounds
synthesized from chemical manipulation of the phytocannabinoid structure. The cannabi-
noids that were newly identified from cannabis were found to be extremely lipophilic and it
was assumed that the action of THC likely occurred through nonspecific interactions within
the neuron membrane (Iversen, 2008). The observation that THC activity was stereospecific
(Mechoulam et al., 1988) led to the search for specific targets that cannabinoids were likely
to bind. In the mid-1980s Allyn Howlett at St. Louis University discovered the cannabinoid
receptor 1 (CB1) in the rat brain (Howlett, Qualy and Khachatrian, 1986; Devane et al.,
1988).
Obviously, a receptor in the brain is present to bind to an endogenous substance and not
to specifically bind to a plant molecule and a search for an endogenous ligand began.
A similar search had occurred earlier in the 1970s after the discovery of opiate receptors
in the brain. That search ultimately led to the discovery of endogenously produced endor-
phins functioning within a previously unknown complex system of opiate receptors in the
brain (Iversen, 2008).
Similar to the discoveries with opiates earlier, within a few years of the identification
of the CB1 receptor, the endogenous cannabinoid, N-arachidonoylethanolamide (ananda-
mide; AEA), an ethanolamine of arachidonic acid, was discovered in pig brain using
radiolabeled ligands by Mechoulam and Devane (Devane et al., 1992). Later, a second
endogenous cannabinoid, 2-arachidonoylglycerol (2-AG), an arachidonate ester of
 Chapter 1: The Botany and History of Cannabinoids 3

glycerol, was identified in canine intestines by the same investigators and in rat brain by
Sugiura and colleagues (Sugiura et al., 1995). Both AEA and 2-AG, referred to as
endocannabinoids since they are synthesized within the body, bind to the cannabinoid
receptor. However, the affinities for the cannabinoid receptors and the chemical structure
of endocannabinoids differ significantly from the familiar three-ring structures of
phytocannabinoids.
This discovery of the CB1 and the binding of AEA and 2-AG was quickly followed by the
identification of a second cannabinoid receptor (CB2), initially located on white blood cells
and spleen suggesting a role for cannabinoids in immune function and protection from
attack and tissue repair (Munro, Thomas and Abu-Shaar, 1993). Although it was originally
believed that the CB2 was only a peripheral receptor, subsequent work found that CB2 is also
present in microglial cells in the brain.
It is possible that more cannabinoid receptors may be found in the future. GPR55 is a G
protein-coupled receptor that binds THC and endocannabinoids (Derocq et al., 1998;
Ryberg et al., 2007). CBD acts as an antagonist on this receptor and the CB1 inverse
antagonist rimonabant acts as an agonist at this site (Pertwee et al., 2005). TRPV1 is another
candidate and is a postsynaptic receptor that binds AEA in addition to activation by
capsaicin. Both AEA and capsaicin bind to the same site within the cell and appear to
mediate pain in sensory neurons (Starowicz and Przewlocka, 2012).

Brief History of Cannabis

The first historical record describing cannabis occurs in ancient Chinese literature dating
from 2727 BC and the Chinese Emperor Shen Nung. Considered the “father of Chinese
medicine,” Shen Nung described hundreds of drugs from plants, animals and minerals in
the Pen Ts’ao, believed to be the first pharmacopeia in history. The Emperor recommended
in his work the use of hemp elixir to treat a wide range of ailments including gout and
malaria. Although the original text no longer exists, the oldest surviving text of the Pen
Ts’ao is found in the first century AD and refers to cannabis as “Ma,” which is the Chinese
word for chaos. We can only conjecture if the meaning of Ma and chaos was intended to
describe the medicinal and psychoactive effects of cannabis. There is little doubt, however,
that the Chinese regarded cannabis as a valuable medicine (Abel, 1980).
Probably as a result of invasion and migration from central Asia, cannabis arrived later
to the subcontinent of India. Although the medicinal uses were also recognized, the Indian
culture embraced cannabis as an important social and religious element. Legend states that
Prince Siddhartha, later named Buddha, survived for six years exclusively on a diet of hemp
seed in his quest for enlightenment. Later in Buddhism, cannabis was reserved for the
priests and upper classes. Cannabis eventually became stratified into three classes: bhang,
ganga and charas (known in other regions as hashish) and the use of cannabis became even
more embedded into Indian culture (Booth, 2004).
Further awareness of cannabis extended beyond India into Persia, Syria and Greece. By
600 BC hemp was brought to the Middle East carried by the Indo-Aryan migration and was
used both as a fiber and a medicine. In Syria cannabis was referred to as “qunubu” or the
“drug for sadness” (Booth, 2004). The Greeks and Romans were certainly aware of cannabis
as hemp and this played an important role in Greco-Roman society. Dioscorides, a Roman
physician trained in the arts of Greek and Oriental medicine served in the Roman army
during the first century AD and wrote De Materia Medica describing the medical uses of
4 Section 1: An Introduction to Cannabinoid Science

cannabis. De Materia Medica would remain among the most influential pharmacopeias in
Western medicine for the next 1700 years (Abel, 1980; Booth, 2004).
In the Muslim era, there was little agreement if cannabis was an intoxicant or a medicine.
In a culture where alcohol was prohibited, cannabis presented daunting religious questions.
One resolution was to severely punish any recreational use of the plant while in other
instances it could be used by physicians to administer treatment (Iversen, 2008).
Other uses were also found in the Muslim world. Hemp was used as a source of paper
and later exported to Europe where it remained a medium of writing and printing until the
introduction of wood pulp in the mid-nineteenth century (Abel, 1980; Booth, 2004)
The first reference to the term “hashish” is found in Egypt during the twelfth century AD
and probably derives from the Arabic word for dried foliage. Hashish contains dried leaves
and flowers along with the highly potent resin that was consumed originally by eating and
not by the more common method today of smoking. The concept of burning dried plants to
activate drug release in smoking was unknown until the sixteenth century with the importa-
tion of tobacco from the new world. Thus, according to legend popularized by the publica-
tion of Marco Polo’s “The Travels of Marco Polo” in the twelfth century, another possible
origin of the word hashish was from “assassins” that described the violent followers of an old
man in the mountains (Booth, 2004).
Several trends converged in the nineteenth century and contributed to the growing
awareness of the medicinal and psychoactive properties of cannabis in Western Europe. In
1839 William Brooke O’Shaughnessy, an Irish physician and professor of chemistry work-
ing for the British East India Company in Calcutta, presented the first medical paper on
cannabis and hashish in western medicine to medical societies in India. In this paper he
described his observations over seven years of the therapeutic effect of cannabis and hashish
in the treatment of seizures, pain, fever and malaria and other conditions. O’Shaughnessy
returned to London in 1842 where he published The Bengal Dispensatory, and Companion to
the Pharmacopoeia that introduced to the British medical societies cannabis and other herbs
used in India. He also provided hashish to a London pharmacist to make a medical extract
with alcohol that was patented and sold as an analgesic. It was this extract that eventually
found its way to North America as Tilden’s Extract. So impactful were these activities that
Queen Victoria is reported to have used cannabis for premenstrual pain (Booth, 2004).
O’Shaughnessy had a brilliant and open mind that saw the therapeutic possibilities of
cannabis although he is better remembered in history for other work. He is credited with the
first use of intravenous fluids for rehydration while a young physician recently out of
training. Later, while in India, he was appointed Director-General of Telegraphs and built
the first telegraph network in India. For this achievement he was knighted in 1856 (Booth,
2004).
Other events also contributed to the growing awareness that cannabis was more than
a source of fiber. In 1796 Napoleon occupied Egypt with the design to disrupt British
trade to the Middle East and India. Although he accomplished this goal of interfering
with commerce, overall the mission was not a success. On August 1–3, 1798 the British
navy under the command of Admiral Horatio Nelson defeated the French fleet at the
Battle of the Nile. This effectively quarantined the French army of 35,000 men in Egypt
and prevented supplies from France reaching them while the British blockaded the ports.
It was during this time as the French were building fortifications to defend their
occupation that the Rosetta Stone was discovered in July 1799 by Pierre-François
Bouchard, an officer and engineer in the French army. Stranded in a Moslem country
 Chapter 1: The Botany and History of Cannabinoids 5

without alcohol, the French soldiers became acquainted with hashish much to the dismay
of Napoleon. On September 2, 1801 the Capitulation of Alexandria was signed and the
French army surrendered and were transported along with their supplies of hashish back
to France by the British navy. The Rosetta Stone became the property of Britain and was
shipped back to London and has been on continuous display in the British Museum since
1802 (Iversen, 2008).
Jacques-Joseph Moreau, a French psychiatrist, also contributed to this raising awareness
about cannabis and hashish after studying about medical practices in India and China for
several years. Returning to France in the 1830s, Moreau was the first to conduct clinical
trials on psychiatric patients and described the effect of cannabis and hashish on the central
nervous system (CNS). Moreau concluded that hashish could mimic mental illness but
recognized that this action might also hold clues to potential treatment. From these
observations the discipline of psychopharmacology arose (Booth, 2004).

Description of the Cannabis Plant

Cannabis is believed by many to have originated in central Asia or in the great river valleys
of eastern China. Cannabis is an annual plant propagated by wind, widely distributed in
temperate and tropical zones, and reported to grow at altitudes up to 8000 feet. The plant
prefers direct sunlight, requires little water, germinates within six days and can reach
maturity within five months. Because of its versatility, it is estimated that cannabis can
grow in over two-thirds of the landmass of the globe (Booth, 2004).
In 1753 Carolus Linnaeus, the Swedish “father of botany,” was aware of cannabis as
hemp and its importance in rope and sail manufacture and named the plant “Cannabis
sativa.” Linnaeus chose the word “cannabis” from the Greek “kannabis” for hemp and
“sativa” from the Latin word for cultivated. The evolutionary biologist Jean-Baptiste
Lamarck in 1783 proposed a second species of the cannabis plant with the name
“Cannabis indica” for a smaller, denser plant that grows in India. Lamarck believed that
there were important distinctions between the two plants and noted that C. sativa possessed
more fiber-like qualities and C. indica had more behavioral effects. Finally, in 1924
Janischewski, a Russian botanist, introduced a third species of cannabis named Cannabis
ruderalis. C. ruderalis is found along the banks of the Volga River and in Siberia (Abel, 1980;
Booth, 2004).
The appearance and geographic distribution of C. sativa and C. indica differ signifi-
cantly. C. sativa is the more widespread of the two with the height of up to 15 feet. In
contrast, C. indica can grow up to 4 feet in height and has dense branching and foliage
(Booth, 2004).
Despite these differences in appearance and properties, controversy remains over
classifying cannabis as several species (polytypic), or as one species (monotypic). Central
to this argument is the belief that the observed differences may reflect the robust adaptability
of the cannabis plant to different climates and soil. This view is based on the observation that
seeds from C. sativa, when planted in regions where C. indica thrive, will over several
generations display many of the characteristics of C. indica. In addition, the various types of
cannabis can easily be interbred, cuttings can be cloned, and hybrids established resulting in
myriad versions of the plant (Booth, 2004; Iversen, 2008).
The male plant produces pollen in the anther within a prominent flower while the
smaller female flower after pollination produces seeds in the perianth.
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