Marijuana Chemistry: Genetics, Processing, Potency

Marijuana

Chemistry

Genetics, Processing, & Potency

by Michael Starks

Ronin Publishing, Inc.

Berkeley, CA

www.roninpub.com

MARIJUANA CHEMISTRY

ISBN: 978-0-914171-39-3

Copyright 1977, 1990 by Michael Starks

Originally published by And/Or Press, Inc. as Marijuana Potency

Published by

Ronin Publishing, Inc.

Post Office Box 3436

Oakland CA 94609

www.roninpub.com

All rights reserved. No part of this book may be reproduced or transmitted in any form or by any means, electronic or mechanical including photocopying, recording, or by any information storage and retrieval system, without written permission from the publisher, except for the inclusion of brief quotations in a review.

Editors: Sebastian Orfali

Production: Sebastian Orfali, Meda Matrix, Paulette Traverso

Photographic credits: pp 104-108 by Irimias the Obscure; pp 2, 88, 103, 126 by Harlan A. Reiders; p 16 by Lew Watts.

Chemical structures on pp 7, 8, and 9 reprinted with permission from R. Mechoulan, Marijuana (Academic Press, NY, 1973).

Appendix on chemical synthesis reprinted with permission from Michael V. Smith, Psychedelic Chemistry (Rip-Off Press, 1973). Illustrations on page 49 reprinted with permission from Joyce & Curry, Botany and Chemistry of Cannabis (Churchill & Livingston, Edinburgh, 1970). Illustrations by D. Eramus.

U.S. Library of Congress Catalog Number 77-82454

Printed in the United States of America

Distributed by PGW/Ingram

NOTICE TO READER:

The material in this book has been published under the freedom afforded by the First Amendment of the U.S. Constitution for reference, informational, and archival purposes only. Neither the author nor the publisher condone or encourage the possession, use, or manufacture of any illegal substances or breaking any laws. Some of the procedures described in this book may be hazardous and should be carried out by trained experts under controlled conditions in a certified laboratory only, and never by an amateur chemist outside of a laboratory. Furthermore, possession of cannabis and hashish is illegal in most areas and doing so endangers your freedom. The author and publisher make no express or implied warranties of any kind regarding the procedures described or of fitness for any purpose with respect to the information in this book. The reader is advised to consult with an appropriate expert, such as an attorney, physician and/or licensed chemists before utilizing any information or carrying out in any procedure in the book.

Table of Contents

Notice to Reader

Abbreviations

Introduction

1.  Marijuana Constitutents and Their Effects

2.  Growth Conditions and Potency

3.  Variations in THC and CBD Content

4.  Variations in Content of Noncannabinoids

5.  Harvesting and Preparing Marijuana and Hashish

6.  Extraction of THC and Preparation of Hash Oil

7.  Isomerization

8.  Testing for THC and CBD Content

Appendix

Notes

Glossary

Bibliography

Marijuana Chemistry Update

Ronin Books-for-Independent-Minds

Abbreviations

Introduction

Psychoactive plants have had an extremely important position in most societies. Consumption of such plants tens or even hundreds of thousands of years ago may have been responsible for generating much of the mythology and religion, indeed, much of the very fabric of culture which so strikingly distinguishes man from even the most advanced of the great apes. Could it be that these plants provided sparks to kindle the flame of intellect which now shines so brightly it threatens to destroy the world? Countless millions of times priests, elders and sages consumed potent preparations of psychoactive plants in order to attune themselves to nature and act in accordance with natural or divine law. This is still done in many of the less technologically evolved societies. The almost universal occurrence of such practices (or their substitutes such as meditation, yoga, trance, hypnosis) testifies to their effectiveness. Western Europe, however, was largely devoid of such plants and consequently of traditions for using them to put oneself in harmony with the surroundings. American traditions have mostly evolved from those of Western Europe and this is one reason for considerable resistance to the use of psychedelic drugs.

Most of the psychoactive plants contain large amounts of alkaloids. These are bitter tasting, nitrogen containing bases which have a wide variety of effects on animals. Why do so many plants contain chemicals that have striking actions on animal nervous systems? Surely the chemicals or some closely related chemicals found in the plants must play important roles in the economy of the plant or else the many genes required for their synthesis would be eliminated by natural selection. In view of the fundamental similarity of all living organisms, it is not surprising that all of them contain chemicals which are active on all the others. Nevertheless, the relatively high concentrations of many psychoactive substances are still puzzling and their precise functions in the plants remain a mystery.

The active chemicals of marijuana, though they are unusual in that they are not alkaloids, do not contain nitrogen and are relatively insoluble in water, likewise have no known reason for being in the plant. However, the psychoactive constituents of Cannabis are unusual, in fact unique, in that they are largely produced in specialized groups of cells termed lactifers, stalked glands and sessile (i.e., not stalked) glands, and in their being released from these cells to form a sticky coating. This will be discussed in more detail later in chapter one.

Before delving into the basic chemistry of Cannabis, a few words of explanation for those unfamiliar with organic chemistry are appropriate. C, H, O, and N refer respectively to atoms of carbon, hydrogen, oxygen and nitrogen. R indicates that a number of different chemical groups (radicals) may occur at this position. In accordance with common conventions, carbon and hydrogen atoms are often omitted in structural formulas. Thus, delta-one-tetrahydrocannabinol shown in figure one actually has 21 carbon atoms and 30 hydrogen atoms. A single line between two atoms indicates a single bond (single pair of shared electrons) while a double line indicates a double bond (two pairs of shared electrons). A double bond is said to be unsaturated because hydrogen or other atoms can be added to it, as when cannabidiol is converted by the plant to THC. Conversely, atoms may be removed from single bonds to produce double bonds as when THC converts to CBN (see figure one). Carbon always has four bonds.

Do not be put off by the chemical formulas and detailed tables in this book—they are absolutely necessary for an adequate understanding of marijuana potency and can be understood by anyone willing to spend a few hours reading. The rewards for making the effort are substantial—you will have a rational, scientific basis for buying, growing, harvesting, storing, preparing, testing and using marijuana and hashish.

1

Marijuana Constituents and Their Effects

Cannabinoids—The Active Chemicals of Marijuana

Although chemical research on marijuana began over 150 years ago, it wasn’t until 1964 that the first authenticated isolation of a pure, active principle delta-one tetrahydrocannabinol (Δ¹-THC) was achieved, and not until 1970 that it was determined to be the only major psychoactive component. Even though dozens of cannabinoids have been isolated since then, none have been found to be significantly psychoactive.

Cannabinoids are the compounds with 21 carbon atoms; they and their carboxylic acids, analogs and transformation products are some of the chemical components of marijuana. Figures 1, 2 and 3 give the structures of a few of these compounds and their probable biosynthetic relationships. Most cannabinoids are extremely insoluble in water, and in the living cell they are probably present entirely as their carboxylic acids. When isolated from fresh marijuana they are usually in their acid form until aging, drying and heat decarboxylate them. The data usually give the percentage of weight of cannabinoids in their neutral form, decarboxylated. The acids are not biologically active, but this is only important if marijuana is eaten or injected, since smoking decarboxylates them. Most marijuana seems to contain largely or exclusively the A form of the acids (shown in figure 2), but variants have been observed which have some of the B form. One Indian variant contained ten times as much A as B and one hashish sample had very little A. These positional isomers have not been investigated much and their significance is unknown.

Δ¹ (⁶)-THC (shown in figure 2) is a minor constituent of marijuana, seldom exceeding more than a few percent of the Δ¹-THC content and having about the same biological activity. It has been suspected of being an artifact of marijuana extraction and analysis.

The biosynthetic route of the cannabinoids (the biochemical pathways by which they are synthesized in the living plant) has not been fully worked out, but the most probable routes are given in figure 3. Starting from precursors such as isoprene or mevalonic acid, compounds of the olivetolic acid and geranyl pyrophosphate type are condensed via intermediates such as cannabigerolic acid to give cannabidiolic acid, which is cyclized to give tetrahydrocannabinolic acid. Time and heat will subsequently cause a certain amount of the THC acid to be dehydrogenated to cannabinolic acid or cannabinol (CBN). At some point, THC and/or cannabidiol (CBD) are extruded through the cell membrane. Whether this happens continually or only after a critical concentration has been reached has not been established: polymers of THC may be formed at this time, but their amounts and possible contribution to marijuana activity have not been investigated.

A great deal of research has been directed at determining the activity of the various chemical constituents of marijuana. One study used the three main compounds, THC, CBD (the biosynthetic precursor to THC) and CBN (the immediate degradation product of THC). The researchers injected measured amounts of each of the compounds in pure form intravenously in human subjects. For THC, it was found that 20 mcg per kilogram of body weight was the average minimum amount perceived to induce a high, while 50 mcg per kilogram was the average maximum amount desired. For CBN these figures were 200 and 270 mcg per kilogram respectively, while for CBD, no high was reported even at 270 mcg per kilogram. However, recent studies show that CBD, while having no direct effect by itself, can have a significant interaction with THC.¹

The Cannabidiol Story

The widely varying effects of marijuana and hashish have long puzzled researchers. If THC is the only psychoactive component, one should get high in proportion to the percentage of THC, especially since studies have shown that pure THC produces essentially the same effects as marijuana. However, the fact is that different samples produce a qualitatively different type of high and that heavy THC content (as in many samples of hashish) does not guarantee a good high. Recent scientific research is helping us to make sense out of this.

Fig. 1. Some naturally occurring cannabinoids. The top three compounds are by far the most important, with the set of three compounds below being identical except that the side chain is shortened by 2 carbon atoms in the cannabidivarol series. Later in the text look for a discussion of the series with the propyl side chain, and see the Appendix for the numbering system used. (Reprinted, by permission, from R. Mechoulam, Marijuana, 1973.)

Fig. 2. Other naturally occurring cannabinoids. (Reprinted, by permission, from R. Mechoulam, Marijuana, 1973.)

Fig. 3. Probable biosynthetic relationships of the major cannabinoids. (Reprinted, by permission, from R. Mechoulam, Marijuana, 1973.)

Fig. 4. Structural aspects of THC. (Reprinted, by permission, from R. Mechoulam, Marijuana, 1973.)

The only compounds that may have effects themselves or may affect the response to THC are CBD and CBN. These two compounds have relatively minor sedative effects in the amounts in which they are likely to be ingested or smoked by ordinary users. Recent studies have shown that they tend to increase the depressant effects of THC while blocking its excitant effects. That is, they tend to make the user sleepy and block the high. The actual situation is more subtle: CBN can synergise with THC to increase mental effects, but CBN will seldom be of consequence in natural situations since it is not usually present in high concentrations and has low potency. Another possibility is that CBD may decrease the depressant effects of THC as well as the excitant effects. Usually, however, as in a recent experiment in which subjects smoked THC with and without CBD (at six times the THC amount) the CBD significantly decreased the euphoria of THC while having no effect itself. When CBD was taken with THC orally at two times the THC amount, it delayed the onset but extended the duration of the high.

The practical conclusions of these findings seem to be: (1) the CBD content of marijuana and hashish should be as low as possible in order to get a good high; (2) a high THC content only means a good high if accompanied by a low CBD content; (3) any grass containing lots of CBD should be extracted and the CBD isomerized to THC; (4) careful evaluation of grass requires quantitative testing for THC and CBD content.

The effects of CBD on the THC high need further investigation, however. It is possible that when present in large amounts, CBD is involved in some of the interesting and pleasurable aspects of the high. It may well be that marijuana that has lots of CBD and THC can be more desirable than that with THC alone. This may be why hashish, though it normally has much less THC than CBD, is frequently a better high than one would expect on the basis of THC content alone.

This could also explain some of the striking differences in subjective experience afforded by different marijuana. As the CBD content increases relative to that of THC, the high will be weakened and delayed. Thus, grass which has an adequate THC content (say 1%) but significant amounts of CBD (say 0.5%) will tend to be very mild, but will slowly creep up on the user and may have him more stoned four hours later than if there were no CBD present. Sometimes this is advantageous; in a recent experiment naïve subjects reported that joints containing CBD with THC were more pleasant than with THC alone. The CBD attenuated the high enough to rid them of anxiety and the jitters.²

Hopefully, it is now clear why the various tables include both THC and CBD. Getting high is becoming a science as well as an art. By paying careful attention to the tables and correlating them with personal experience, it may eventually be possible to judge fairly closely the nature of the high obtainable from a given marijuana sample. Simple, rapid chemical tests for home use will soon be available for the determination of THC and CBD content. Merely knowing the origin of the seeds can also give a good gauge for evaluating the quality of the resulting marijuana crop, regardless of where it is being grown. Of course, differences in seeds, growth conditions and age will still produce considerable variation, but seeds from high THC plants will usually grow into high THC plants.

To summarize, the cannabidiol story is confusing because of the complex nature of its interactions with THC and because relatively little research has been done.