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Cannabinoids are terpenophenolic compounds chemically related to the terpenoid com- pounds as the ring structure is derived from a geranyl pyrophosphate C 10 terpenoid subunit. Cannabinoids are not significantly present in extracts prepared by steam distillation Cannabis and Natural Cannabis Medicines 7 Our basic understanding of the biosynthesis of the major cannabinoids comes largely from the research of Yukihiro Shoyama and colleagues at Kyushu University in Japan 16, T, D, and C, respectively.

The three enzymes can likely use either propyl CBGV or pentyl CBG for the propyl and pentyl pathways, depending on which substrate is available. This hypothesis was verified by Flachowsky et al. Continued research by de Meijer et al. The group also identified by random ampli- fied polymorphic DNA analysis three chemotype-associated DNA markers that show tight linkage to chemotype and co-dominance. Medical Values of Terpenes The terpenoid compounds found in Cannabis resin are numerous, vary widely among varieties, and produce aromas that are often characteristic of the plant's geo- graphic origin.

Although more than different named terpenes have been identified from Cannabis, no more than 40 known terpenes have been identified in a single plant sample, and many more remain unnamed Terpenes are produced via multibranched biosynthetic pathways controlled by genetically determined enzyme systems. This situ- ation presents plant breeders with a wide range of possible combinations for develop- ing medical Cannabis varieties with varying terpenoid profiles and specifically targeted medical uses.

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Preliminary breeding experiments confirm that the terpenoid profiles of widely differing parents are frequently reflected in the hybrid progeny. Only recently have Cannabis essential oils become economically important as flavorings and fragrances Early Cannabis medicines were formulated from alco- holic whole flower or resin extracts and contained terpenes, although they were not recognized to be of medical importance.

Several of the monoterpenes and sesquiterpe- nes found in Cannabis and derived from other botanical and synthetic sources are used in commercial medicines. Other as-yet-unidentified terpenes may be unique to Cannabis. The highly variable array of terpenoid side-chain substitutions results in a range of human physiological responses.

Certain terpenes stimulate the membranes of the pulmonary system, soothe the pulmonary passages, and facilitate the absorption of other compounds Terpenoid compounds are incorporated into pulmonary medi- cal products such as bronchial inhalers and cough suppressants. Casual studies indi- cate that when pure THC is smoked, it produces subjectively different effects than it does when combined with trace amounts of mixed Cannabis terpenes. Cannabinoid biosynthesis is mediated by enzymes controlled by individual genes Terpenoid biosynthesis also begins along the same general pathway by utilizing geraniol molecules directly.

Cannabis 's Origin, Domestication, and Dispersal Cannabis originated either in the riverine valleys of Central Asia or in northern South Asia along the foothills of the Himalayas and was first cultivated in China on a large scale for fiber and seed production and soon after in India for resin production. Various cultures have traditionally used Cannabis for different purposes. European and East Asian societies most often used Cannabis for its strong fibers and nutritious seeds.

Central Asian hashish varieties, popularly called "indicas," were introduced to the West much more recently. Drug Cannabis use was adopted by indigenous cultures in many of these locations, and highly psychoactive races evolved. All modern drug varieties used as medical Cannabis are derived from these two tradi- tional drug variety gene pools. Certainly, the enchanting psychological and effective medical effects realized from smoking or eating Cannabis resins, along with its value as a food and fiber plant, have increased predation by humans, encouraged its early domestication as a crop plant, and hastened its dispersal worldwide first into natural and, more recently, into artificial environments.

Although all taxonomists recognize the species Cannabis sativa, Small and Cronquist 20 sub- divided C. Several other researchers do not preserve C. These morphologically and chemically distinct Central Asian races deserve the separate spe- cific name of C. Some Chinese races may also deserve taxonomic distinc- tion separate from either C.

Validation of these theories awaits further chemotaxonomic and genetic research. In all of these taxonomic interpretations, C. Individual plants of these hashish varieties have their own dis- tinctive acrid organic aromas and are often rich in CBD as well as THC. The wide variety of morphological, physiological, and chemical traits encountered in Cannabis has proven very attractive to plant breeders for years. At first, Cannabis seeds found in illicit shipments of marijuana were simply casually sown by curious smokers. Early marijuana cultivators tried any available seed in their efforts to grow potent plants outdoors that would consistently mature before killing frosts.

Because most imported marijuana contained seeds, many possibilities were available. Early-maturing northern Mexican varieties proved to be the most favored, as they consistently matured at northern latitudes. The legendary domestic Cannabis varieties of the early and mids such as Polly and Haze resulted from crosses between early-maturing Mexican or Jamaican races and more potent, but later-maturing, Pana- manian, Colombian, and Thai races. The four major Cannabis gene pools originate either from C. Initially, the new Cannabis varieties were aimed at outdoor growing.

Soon oth- ers were specially developed for greenhouse or artificial light growing, where the plants are sheltered from autumn cold and the growing season can be extended by manipulating day length, allowing later-maturing varieties to finish. Once varieties that would mature under differing conditions were available, pioneering marijuana breeders continued selections for potency high THC content with low CBD content followed by the aesthetic considerations of flavor, aroma, and color. The Introduction of Indica Indica plants are characterized as short and bushy with broad, dark green leaves, which make them somewhat harder to see from afar.

They nearly always mature quite early outdoors, from late August to early October, often stand only m 3- 6 ft. At least several dozen introductions of indica were made during the middle to late s. Following the Soviet invasion of Afghanistan in , many additional introductions were made from Afghanistan and northwest- ern Pakistan. Cannabis and Natural Cannabis Medicines 7 7 Marijuana breeders intentionally crossed varieties of early-maturing indica with their later-maturing sativa varieties to produce early-maturing hybrid crosses matings of parents from different gene pools , and soon the majority of cultivators began to grow the newly popular indica x sativa hybrids.

Many of the indica x sativa hybrids were vigorous growers, matured earlier, yielded well, and were very potent. By the early s, the vast majority of all domestic sinsemilla in North America had likely received some portion of its germplasm from the indica gene pool, and it had become difficult to find the preindica, pure sativa varieties that had been so popular only a few years earlier. However, the negative characteristics of reduced potency lower THC content ; slow, flat, sedative, dreary effect high CBD content ; skunky, acrid aroma; and harsh taste quickly became associated with many indica x sativa hybrids.

To consumers, who often prefer sativas, indica has not proven itself to be as popular as it is with growers. Also, the dense, tightly packed floral clusters of indica tend to hold moisture and to develop gray mold Botrytis , for which the plants have little natural resistance. Mold causes significant losses, especially in outdoor and glasshouse crops, and was rarely a problem when only pure C. In addition, fungal contamination of medical Cannabis could prove a serious threat to pulmonary or immunocompromised patients.

Although consumers and commercial cultivators of the late s initially accepted indica enthusiastically, serious breeders of the late s began to view indica with more skepticism. Although indica may currently appear to be a growing bane for Cannabis connoisseurs, it has certainly been a big boon for the average consumer, bringing more potent and medically effective Can- nabis to a wider audience. Indica x sativa hybrids have proven to be well adapted to indoor cultivation where mold is rarely a problem.

Indica x sativa varieties mature quickly days of flowering , allowing four to five harvests per year, and can yield up to g of dry flowers on plants only 1 m 3 ft. On the other hand, sativas have unique cannabinoid and terpenoid profiles producing effects considered superior by many medical Cannabis users. Political pressure on marijuana cultivators across North America forced many drug Cannabis breeders to relocate to the Netherlands, where the political climate was less threatening. During the s, several marijuana seed companies appeared in the Netherlands, where cultivation of Cannabis for seed production and the sale of seeds were tolerated.

To North American and European cultivators, this meant increased availability of exotic high-quality drug Cannabis seeds and presented yet more possi- bilities to find varieties that were the most medically effective for individual indica- tions and patients. Cannabis seed sales continue in the Netherlands today. Advances in Medical Cannabis Research Cannabis available to the medical user comes in two commonly available types. Very high THC with negligible CBD profiles of modern sinsemilla varieties result from marijuana growers sampling single plants and making seed selections from vigorous individuals with high levels of psychoactivity.

Unique individuals may also be vegetatively propagated, thereby fixing the high-THC geno- type in the clonal offspring. Imported hashish is produced by bulk processing large numbers of plants. Growers rarely make seed selections from individual, particularly potent plants, and therefore without human intervention the CBD content tends to be closer to that of THC.

Hashish cultivars are usually selected for resin quantity rather than potency, so the farmer chooses plants and saves seeds by observing which ones produce the most resin, unaware of whether it contains predominantly THC or CBD. CBD is suspected of having modifying physiological and psychological effects on the primary psychoactive compound THC, and in a medical setting it may also have useful modulating effects on THC or valuable effects of its own.

However, ana- lytical surveys of 80 recreational and medical Cannabis varieties in the Netherlands 26 and 47 samples in California 27 show that nearly every sample contained pre- dominantly THC with little if any CBD or other cannabinoids. Higher levels of THC and other medically effective cannabinoid and terpenoid compounds in medical Cannabis are healthier for patients using smoked Cannabis because they can smoke less to achieve the same dosage and effect. Proponents of medical Cannabis, especially traditional hashish users, claim that the additional benefits of herbal preparations are a result, at least in part, of the pres- ence of other cannabinoids such as CBD.

Because THC with traces of CBD is the prominent cannabinoid found in most domestically produced North American and European marijuana and hashish, how will medical users gain legitimate legal access to other potentially effective cannabinoids? The Future of Medical Cannabis Cannabis breeders are continually searching for new sources of exotic germplasm and will develop new varieties that will prove particularly effective as medicines.

Both recreational and medical Cannabis typically originate from either seeded plants used primarily for traditional hashish production or seedless plants grown primarily for "sinsemilla" marijuana and occasionally for modern hashish production. Pure indica varieties are still highly prized breeding stock, and new indica introduc- tions from Central Asia are occasionally received.

Sativa varieties from Mexico, South Africa, and Korea are gaining favor with breeders because they mature early but do not suffer from the drawbacks of many indicas. Recently, Cannabis breeders have become more interested in variations in subjective effects between different clones and are developing varieties with enhanced medical efficacy based on feedback from medical Cannabis users. Genetic modification has also reached Cannabis.

Researchers in Scotland have successfully transferred genes for gray mold resistance to an industrial hemp variety Because Botrytis is one of the leading pests of Cannabis, causing crop loss and contaminating medical supplies, the transfer of resistance into medical varieties would be of great value. In addition, other agronomically valuable traits may also be trans- ferred to Cannabis, such as additional pest resistance, increased yields of medically valuable compounds, tolerance of environmental extremes, and sexual sterility.

How- ever, so far the acceptance of genetically modified GM organisms has been timid. The European Union, for example, has installed strict regulations to prevent the acci- dental release of GM crop plants, and production of GM Cannabis in the European Union may be impractical. Cannabis presents a particularly high risk for transmitting genetically modified genes to industrial hemp crops and weedy Cannabis because it is wind-pollinated.

If sterile female GM clones could be developed and used for produc- tion, then gene transfer would be blocked. Genes coding for cannabinoid biosynthesis might also be transferred from Cannabis to less politically sensitive organisms. The aims of this research are to create varieties that produce only one of the four major cannab- inoid compounds e.

These uniform profiles allow for the formulation of nonsmoked medicinal prod- ucts, which can meet the strict quality standards of international regulatory authorities. A sublingual spray application of plant-derived THC and CBD began clinical trials for relief of multiple sclerosis-associated symptomology in These clinical trials have gone on to include patients with neuropathic pain and cancer pain.

Conclusion Cannabis has had a long association with humans, and anecdotal evidence for its medical efficacy is plentiful. Since the s, modern North American and European drug Cannabis varieties have resulted largely from crosses made by clandestine breeders between South Asian sativa marijuana varieties that spread early throughout South and Southeast Asia, Africa, and the New World and Central Asian indica hashish varieties. These hybrid varieties are now commonly used in Western societies for medical Cannabis.

Largely as a response to increased law enforcement and the limited commercial availability of high-quality medical grade Cannabis, patients growing their own plants and self-medicating is a trend rapidly spreading across North America, Europe, and around the globe. The political climate surrounding medical Cannabis legislation has become more informed, compassionate, and lenient. Cannabis cultivation for personal medical use will eventually be legalized or tolerated in many jurisdictions, if not by the public openly favoring legalization, then by increasing governmental awareness of the inefficiency inherent in attempted prohibition of a popular and effective medicine.

Pharmaceutical research companies are developing new natural cannabinoid for- mulations and delivery systems that will meet government regulatory requirements. As clinical trials prove successful and the understanding of Cannabis' 's efficacy and safety as a modern medicine spreads, patients can look forward to a steady flow of new Cannabis medicines providing effective relief from a growing number of indica- tions.

Cannabis and Natural Cannabis Medicines 15 6.

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China's Fibre Crops 2, 19, 29 [in Chinese]. C, and Watson, D. Pharmacology and Therapeutic Potential Grotenhermen, F. Biochemical analysis of a novel en- zyme that catalyzes the oxidocyclization of cannabigerolic acid to cannabidiolic acid. Botanical Museum Leaflets, Harvard University 23, Introduction The Cannabis plant and its products consist of an enormous variety of chemi- cals.

Some of the compounds identified are unique to Cannabis, for example, the more than 60 cannabinoids, whereas the terpenes, with about members forming the most abundant class, are widespread in the plant kingdom. The term "cannab- inoids" represents a group of C 2] terpenophenolic compounds found until now uniquely in Cannabis sativa L. As a consequence of the development of synthetic cannab- inoids e. Chemistry and Classification So far, 66 cannabinoids have been identified.

They are divided into 10 subclasses see Table 1.

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CBG was the first cannabinoid identified 11 , and its pre- cursor cannabigerolic acid CBGA was shown to be the first biogenic cannabinoid formed in the plant Propyl side-chain analogs and a monomethyl ether deriva- tive are other cannabinoids of this group. Five CBC-type cannabinoids, mainly present as C5- analogs, have been identified. CBD was isolated in 13 , but its correct structure was first elucidated in by Mechoulam and Shvo Iso- lated in , CBDA was the first discovered cannabinoid acid. A 9 -Tetrahydrocannabinol THC type: THC is the main psychotropic prin- ciple; the acids are not psychoactive.

A 8 -THC type: The 8,9 double-bond position is thermodynamically more stable than the 9,10 position. Three cannabinoids characterized by a five-atom ring and Cj-bridge instead of the typical ring A are known: CBL, its acid precursor, and the C 3 side-chain analog. Their concentration in Cannabis products depends on age and storage conditions. CBN was first named in 1 by Wood et al. Nine CBT-type cannabinoids have been identified, which are characterized by additional OH substitution. CBT itself exists in the form of both isomers and the racemate, whereas two isomers 9-a- and 9-b-hydroxy of CBTV were identified.

CBDA tetrahydrocannabitriol ester ester at 9-hydroxy group is the only reported ester of any naturally occurring cannabinoids. Eleven cannabinoids of various unusual structure, e. The mean THC concentra- tion increased from less than 1. The maximum levels found were The highest THC concentrations measured were Two studies performed in Switzerland from to 20 and to 21 found mean THC concentrations in marijuana samples of 1.

Maximum levels were 4. Reasons for this enormous increase in potency include progress in breed- Chemistry of Cannabis Constituents Table 1 continued 27 Compound Structure Main pharmacological characteristics 3,4,5,6-Tetrahydro hydroxy-alpha-alpha trimethyln-propyl-2,6- methano-2Hbenzoxocin- 5-methanol OH-iso-HHCV Cannabiripsol CBR C 5 H 11 Trihydroxy-delta tetrahydrocannabinol triOH-THC ing, the tendency to cultivate under indoor conditions, and the worldwide access to and exchange of seeds originating from high-THC cultivars via the Internet THC in Hemp Seed Products The presence of THC in hemp seed products is predominantly the result of exter- nal contact of the seed hull with cannabinoid-containing resins in bracts and leaves during maturation, harvesting, and processing The seed kernel is not entirely free of THC but contains, depending on the hemp variety, less than 0.

These high levels were attributed to seeds from THC-rich, "drug-type" varieties, and the lack of adequate cleaning procedures. In recent years, more careful seed drying and cleaning have considerably lowered the THC content of seeds and oil available in the United States 23, Terpenoids The typical scent of Cannabis results from about different terpenoids. Iso- prene units C 5 H g form monoterpenoids C, skeleton , sesquiterpenoids C 15 , diterpenoids C 20 , and triterpenoids C 30 ; see Table 2.

Terpenoids may be acyclic, monocyclic, or polycyclic hydrocarbons with substitution patterns including alcohols, ethers, aldehydes, ketones, and esters. The essential oil volatile oil can easily be obtained by steam distillation or vaporization. The yield depends on the Cannabis type drug, fiber and pollination; sex, age, and part of the plant; cultivation indoor, outdoor etc. For example, fresh buds from an Afghani variety yielded 0. Drying and stor- age reduced the content from 0. Monoterpenes showed a significantly greater loss than sesquiterpe- nes, but none of the major components completely disappeared in the drying process.

In the essential oil from outdoor-grown Cannabis, the monoterpene concentration varied between The sesquiterpenes ranged from 5. The most abundant monoterpene was 3-myrcene, followed by frarcs-caryophyllene, a-pinene, fraTis-ocimene, and a-terpinolene. Even in "drug-type" Can- nabis, the THC content of the essential oil was not more than 0.

In the essential oil of five different European Cannabis cultivars, the dominating terpenes were myrcene The main differ- ences between the cultivars were found in the contents of a-terpinolene and a-pinene. Other terpenoids present only in traces are sabinene, a-terpinene, 1,8-cineole eucalyptol , pulegone, y-terpinene, terpineolol, bornyl acetate, a-copaene, alloaromadendrene, viridiflorene, 3-bisabolene, y-cadinene, fra? Hydrocarbons The 50 known hydrocarbons detected in Cannabis consist of rc-alkanes rang- ing from C 9 to C 39 , 2-methyl-, 3-methyl-, and some dimethyl alkanes 10, The major alkane present in an essential oil obtained by extraction and steam distilla- tion was the n-C 29 alkane nonacosane Other abun- dant alkanes were heptacosane, 2,6-dimethyltetradecane, pentacosane, hexacosane, and hentriacontane.

Nitrogen-Containing Compounds Cannabis sativa L. However, two spermi- dine-type alkaloids see Table 3 have been identified among the more than 70 nitro- gen-containing constituents. Other nitrogenous compounds found are the quartenary bases choline, trigonelline, muscarine, isoleucine betaine, and neurine. Twelve simple amines, including piperidine, hordenine, methylamine, ethylamine, and pyrrolidine, are known. The 18 amino acids are of a struc- ture common for plants. Carbohydrates Common sugars are the predominant constituents of this class.

Thirteen monosacharides fructose, galactose, arabinose, glucose, mannose, rhamnose, etc. Orientin, vitexin, luteolinO-glucoside, and apigeninOglucoside were the major flavonoid glyco- sides present in low-THC Cannabis cultivars The cannflavins A and B are unique to Cannabis 38, Fatty Acids A total of 33 different fatty acids, mainly unsaturated fatty acids, have been iden- tified in the oil of Cannabis seeds.

N one annabinoid Phenols Thirty-four noncannabinoid phenols are known: Other Among the 1 1 phytosterols known are campesterol, ergosterol, 3-sitosterol, and stigmasterol. Vitamin K is the only vitamin found in Cannabis, whereas carotene and xanthophylls are reported pigments. Eighteen elements were detected e. Pharmacological Characteristics of Cannabinoids and Other Cannabis Constituents THC is the pharmacologically and toxicologically most relevant and best stud- ied constituent of the Cannabis plant, responsible for most of the effects of natural Cannabis preparations A MEDLINE search covering the period and using the keywords "tetrahydrocannabinol" and "pharmacology" produced about citations.

A review of the pharmacology, toxicology, and therapeutic potential of Can- nabis, cannabinoids, and other Cannabis constituents is given in refs. It is claimed that Cannabis as a polypharmaceutical herb may provide two advantages over Chemistry of Cannabis Constituents Table 6 continued 39 Compound Structure Glucose [ ho. Thus, Cannabis has been characterized as a "synergistic shotgun," in contrast, for example, to dronabinol synthetic THC, Marinol 8 , a single-ingredient "silver bullet" A recent study compared the subjective effects of orally administered and smoked THC alone and THC within Cannabis preparations brownies, cigarettes; refs.

THC and Cannabis in both application forms produced similar, dose-dependent subjective effects, and there were few reliable differences between the THC-only and whole- plant conditions. An overview of the pharma- cology and clinical relevance of CBD can be found in refs. Of clinical relevance could be its reported ability to reduce anxiety and the other unpleasant psy- chological side effects of THC.

Among the underlying mechanisms is the potent inhi- bition of the cytochrome P 3A1 1, which biotransforms THC to the fourfold more psychoactive hydroxy-THC Whereas the anti-inflammatory and antibiotic activity of Cannabis terpe- noids is known and has been used therapeutically for a long time, the serotonergic effect at 5-HT 1A and 5-HT 2A receptors of the essential oil, which could explain Can- nabis -mediated analgesia and mood alteration, has only recently been demonstrated P-Myrcene, the most abundant monoterpene in Cannabis, has analgesic, anti- inflammatory, antibiotic, and antimutagenic properties The pharmacological effects of other Cannabis terpenes are discussed by McPartland and Russo Apigenin, a flavonoid found in nearly all vascular plants, excerts a wide range of biological effects, including many properties shared by terpenoids and cannabinoids.

It selectively binds with high affinity to benzodiazepine receptors, thus explaining its anxiolytic activity The pharmacology of other Cannabis flavonoids is reviewed in ref. Analysis of Phytocannabinoids Instrumental methods are most often used for the identification, classification e. However, especially for screening purposes and on-site field testing, noninstrumental techniques like thin-layer chromatography TLC and color reactions are helpful, too. Microscopy Identifying a plant sample as Cannabis sativa L. The botanical identification of plant specimens consists of physical examination of the intact plant 42 Brenneisen morphology and habit leaf shape, male and female inflorescenses, etc.

The very abundant trichomes, which are present on the surface of the fruiting and flowering tops of Cannabis, are the most characteristic features to be found in the microscopic examination of Cannabis products not liquid Cannabis, hashish oil. Sometimes microscopic evidence is still available in smoked Cannabis residues. Color Reactions It must be stressed that positive reactions to color tests are only presumptive indications of the possible presence of Cannabis products or materials containing Cannabis products. A few other materials, often harmless and uncontrolled by na- tional legislation or international treaties, may react with similar colors to the test reagents.

It is mandatory for the laboratory to confirm such results by the use of an alternative technique, which should be based on MS The most common color spot tests include those developed by Duquenois and its modifications A study of different plant species and organic compounds has shown that the Duquenois-Levine modification is most specific The fast blue B salt test is the most common color reaction for the visualization of TLC patterns but may also be used as spot test on a filter paper Thin-Layer Chromatography One- and two-dimensional TLC is suited for the acquisition of qualitative can- nabinoid profiles from plant material 70,73,75, Fast blue salt B or BB are used for visualization and result in characteristically colored spot patterns For quantitation, instrumental TLC coupled to densitometry is necessary.

High-pressure TLC and overpressured layer chromatography have been developed for the reproduc- ible and fast determination and isolation of neutral and acidic cannabinoids Derivatization is nec- essary e. The total cannab- inoid content, i. High-Performance Liquid Chromatography High-performance liquid chromatography makes possible the simultaneous determination of neutral and acidic phytocannabinoids without derivatization.

Cannabis Is In Your DNA

Reversed- phase columns and preferably solvent programmed gradient systems are required for the separation of major and minor cannabinoids and their corresponding acids, e. Detection is usually performed by UV 70,80,87, and diode array photometers 93 , as well as by fluores- cence, electrochemically , and, recently, MS Other Techniques The applicability of capillary electrochromatography with photodiode array UV detection for the analysis of phytocannabinoids has been demonstrated DNA Testing After a Cannabis sample has been identified and classified, it may become important to individualize the specimen for forensic and intelligence purposes Tracing the source of origin can be performed on a chemical, e.

For DNA profil- ing 22, 10 , the following techniques are used: An overview and description of the different DNA testing methods is given in ref. A preliminary review of its pharmacological properties and therapeutic use. Tet- rahedron Asymmetry 1, Fatty Ac- ids 53, A review of the natural constituents. The structure of cannabidiol. Tetrahe- dron 19, The resin of Indian hemp.

Synthesis of cannabinol, l-hydroxyn-amyl-6,6,9-trimethyldibenzopyran. Chemistry of Cannabis Constituents 45 Vanhoenacker, G, Van Rompaey, P. CNS Drugs 17, A qualitative systematic review. P sy chop ha rmaco logy , Chemistry of Cannabis Constituents 47 C, and Moulin, M. C, and Camsonne, R. Determination of cannabinoids in Can- nabis sativa L.

Rustichelli, C, Ferioli, V. C, and Gamberini, G. Chemistry of Cannabis Constituents 49 1 Set Justice 38, Introduction Marijuana is the most widely abused and readily available illicit drug in the United States, with an estimated Drug enforcement agencies are therefore keenly interested in trafficking routes of both foreign and domestically grown supplies of marijuana. From confidential sources to satellites, these agencies employ a multitude of methods to gather intelligence to direct resources, plan control operations, and develop poli- cies.

A practical means to recognize the source of seized marijuana would be a valu- able tool for those purposes. Based on findings from to and described here, one way to determine origin is by using a chemical fingerprint system, a method that has shown promise as an effective intelligence tool to ascertain the geographic origin of confiscated marijuana samples. Of the many factors that affect the chemical con- stituents of marijuana, it is apparent that environmental factors consistently induce profiles unique to each environ. An "environ of origin" as broad as a continent or as small as an indoor garden may be differentiated based on the chemical fingerprint, or "signature," of marijuana cultivated there — if a statistically significant number of samples grown in that environ are available for comparison.

However, because all environs are not unique, the chemical fingerprint of cannabis is not considered to be an ultimate tool for forensic applications, although the technique may effectively sup- From: Scientists have developed sophisticated techniques to study the unique patterns of the infinite combinations of chemical compounds making up specific materials and have applied those techniques to various disciplines. Over some 35 years, a number of researchers have examined the chemical com- pounds unique to the Cannabis plant and have consistently reported that the "cannab- inoids" are indicative of the country of origin and that environmental factors affect cannabinoid profiles.

During the s a number of publications appeared that used gas chromatography GC , thin-layer chromatography, and high-performance liquid chromatography techniques to compare cannabinoid concentrations of marijuana grown in various regions of the world In the s and s those technologies advanced greatly, and researchers continued to reach similar conclusions Marijuana from different geographical regions has also been compared using other analytical techniques, including elemental analysis 20,21 , GC analysis of headspace volatiles 22 , analysis of free sugars in the plants 23 , microscopic examination of pollen 24 , and even comparison of insect species found in confiscated materials 25, Nearing the 21st century, as technologies further advanced, scientists turned their attention to genetic analyses of marijuana and developed techniques very suitable for forensic purposes Examination of the DNA of marijuana plants now allows forensic investigators to identify even minute particles as Cannabis and to determine whether a sample is from the drug or the fiber type of the plant.

Just as human DNA testing has revolutionized criminology, so has the genetic testing of marijuana given prosecutors a reliable means to assert that the stash in a defendant's pocket was har- vested from the plant found under a grow light in his basement. However, DNA test- ing can be expensive and time-consuming and only reflects a plant's lineage, not the environment in which it was grown.

One part of that mission is to manage a national drug intelligence program. To collect, analyze, and disseminate intelligence information at federal, state, local, and foreign levels, the DEA uses scientific technologies to help gather the pieces of the worldwide puzzle of drug trafficking.

In , the DEA initiated the Heroin Signature Program to enhance the agency's ability to identify the source of heroin seized or purchased within the United States. Following the success of that program, a similar program for cocaine profiling was set up in , and a methamphetamine profiling program in In the mids, realizing the potential value of a fully integrated "cannabis fingerprint system" including standardized equipment and methods, a database for reference, and an automated means to interpret data, officials turned to the scientific community for assistance.

ELI , to develop analytical methodologies that could be used to compare complete chemical finger- prints of Cannabis samples of different geographical origins. At that time, the DEA Chemical Fingerprinting of Cannabis 53 also provided funds to conduct a feasibility study to demonstrate if a practical chemi- cal fingerprint system could be developed.

In , ELI reported positive results and as a result the DEA funded a phase II study beginning in to develop a fully operational Cannabis fingerprint system and to establish an initial database of mari- juana fingerprints from major production regions. Law enforcement agencies agreed to provide marijuana samples of presumed authenticity specifically chosen to build a useful data- base of major production areas.

To avoid bias, statistical software was used to analyze the data. At the time of the phase I study, the science of chemometrics — the application of statistics and mathematical methods to chemical data — was a burgeoning field within the computer science and analytical chemistry communities. Although standardized pattern-matching software was just beginning to become available, an in-house pro- gram was developed by ELI personnel to analyze the data. At the conclusion of the study an independent chemometrics company, InfoMetrix, was enlisted to evaluate the data using various pattern recognition and statistical methods to further validate the concept of a turnkey system.

Their report in March stated that, based on studies using their own statistical software, the concept was indeed viable, that every sample of foreign origin had been correctly classified by country of origin, and that every sample of domestic origin had been correctly classified by state of origin. At this writing, the latest version of Pirouette is marketed as their most comprehensive chemometrics software used to discover associations of patterns in data and to prepare and use multivariate classification models.

Pirouette, like all commercial software, has dramatically evolved in the past 15 years, but the early version used in the phase II study perfectly suited the requirements at the time, including the capability for interlaboratory data sharing. Its graphical interface allowed us to view a three-dimensional representation of an unknown sample compared to a model and to rotate the image in order to actually see the relationships of the principal chemical components.

Mathematical algorithms such as principal component analysis and hierarchical cluster analysis were used to reduce the large complex data sets into comprehensible forms The graphic views emphasized the natural groupings in the data and showed which variables most strongly influenced those patterns. The basis of the project was to first construct a "model," that is, a set of data that represented the chemical finger- print of a plant typical of the "class" to which it is assigned, in this case a country, a 54 ElSohly et al. The suc- cess of the study hinged on how well the models could be built — a daunting task.

To validate proposed multivariate models, "training sets" of data known to be representative of the various classes were processed. Once Pirouette was trained to recognize classes using a K-nearest-neighbor modeling technique 32 , data from samples of unknown origin could be tested and shown to be either in or not in a certain class or perhaps overlapping two or more classes. Based on the amount of variance in the model, Pirouette also provided a measure of the probability of the accuracy of the results, i. Chemical Constituents of Cannabis Many of the chemical constituents of Cannabis are common to other plants; how- ever, cannabinoids are unique to their namesake Of the hundreds of chemicals found in Cannabis — and described at length in this book — were used to develop the chemical fingerprint system.

Of those compounds readily detectable by the meth- ods developed in phase I, 46 were positively identified, including 22 monoterpenes or sesquiterpenes, 16 cannabinoids, two noncannabinoid phenols, two hydrocarbons, three fatty acid esters, and one miscellaneous aromatic compound see Table 1. The remaining compounds were necessarily included because all of the chemical com- pounds contribute to the fingerprint, and only the multivariate data analysis software could sort out which ones were important to establish relationships and differentiate between the classes.

For the fingerprint system to be of practical use in all laboratories, the methods needed to be reproducible and cost-effective, so simple methods using common labo- ratory equipment were developed. The methods used in this study have not been vali- dated for reproducibility between different laboratories, but because of the simple analytical techniques employed we assumed that the methods would be robust and that different laboratories could generate similar data in house.

Because the finger- print chromatograms are so complex, however, it may be difficult to compare data generated at different laboratories. Interlaboratory variation in signature analysis is a common and vexing problem in this field; for this reason, the DEA has centralized its signature programs at a single, specialized laboratory.

Although all of the compounds mak- ing up the standardized fingerprints could not be specifically identified even though the spectral evidence suggested some possibilities , each was numbered for reference. For the study to be complete, however, it was necessary to identify as many of the compounds as possible to better grasp the relationships of the chemical finger- prints to their environs.

Several techniques were employed in order to understand the makeup of the chemical fingerprints. The terpenes were of great interest because their production by plants was likely to consistently reflect the immediate environment, whereas the cannabinoids would tend to reveal genetic relationships. Experimental Design The specific goal of the study was to develop a fully operational fingerprint sys- tem that could be used to determine the probability that a particular marijuana sample of unknown origin had been grown in one of the target foreign countries or domestic states or other environs in the database.

The top priority for the experimental design was to be able to distinguish between foreign and domestically produced marijuana in order to determine the prevalence of foreign material entering the country vs domestic material being trafficked. The second objective was to accurately determine the coun- try of origin. The third goal was to provide a method to accurately estimate the ratio of indoor vs outdoor domestic production. Determination of the state of origin of plants grown outdoors in the United States was of lower priority.

Specimens, or "exhibits," from the various regions known to be major contribu- tors to the illicit marijuana market in the United States were submitted by law enforce- ment agencies. To ensure the validity of the origins of the specimens, they were shipped directly from the areas of collection and were therefore presumed to represent true authentics.

Both marijuana and hashish specimens were made available for the study. Samples were usually analyzed within 4 weeks of preparation. Of the marijuana exhibits representing six regions, passed the initial quality control QC requirements of specimen integrity designed to ensure represen- tative fingerprints.

Freely available

To ensure consistency, only mature female plants were included in the study. Specimens that could not be determined to be from mature plants no buds or seeds , those in poor condition molded or decayed , those contaminated with soil, and those composed of mostly seeds, stems, and roots but lacking suitable leaf mate- rial were rejected. The exhibits from regions included in the phase II database in- cluded 26 Colombian, 35 Jamaican, 20 Mexican, 30 Thai, 25 Californian, and 21 Hawaiian samples.

Of course, Hawaiian marijuana was expected to have a fingerprint with foreign traits. The original study also included 17 exhibits from Tennessee that were not defi- nitely mature but were included in the study to provide data from the eastern United States. We have chosen to exclude those data here because the profiles of the Tennes- see exhibits were shown to be unreliable, which could be related to their stage of maturity. The exclusion of these data had no effect on the conclusions of the study. Because marijuana grown under controlled conditions was necessary to support the fingerprint studies, several growing experiments were carried out at the UM mari- juana garden during both phase I and II periods.

Second-generation daughter plants were grown from seeds collected from 38 phase I exhibits to compare the fingerprints of genetically equivalent plants grown outside the country of origin. Two experiments were conducted to compare the fingerprints of plants grown indoors to those grown outdoors. To study how the chemical fingerprints of both sexes of marijuana plants vary at different stages of plant maturity, leaf samples were collected at regular intervals from plants of Mexican origin grown outdoors.

Specimens from five male and five female plants were analyzed to study how their fingerprints developed at 8, 12, 16, 20, and 25 weeks of age. Because many chemical compounds readily decompose, given time, and because the decomposition generally occurs more rapidly at elevated temperatures, a study was initiated to determine how fingerprints change during the time between the col- lection of exhibits and their transfer to a freezer.

For this experiment, 80 specimens from the UM garden were stored in paper bags both at room temperature and at an elevated temperature and then transferred to a freezer after and day intervals. Because of the inherent nature of hashish, a refined product made from the resin of Cannabis and intended for commerce, all of the available exhibits were suitable for chemical analysis, except that several localities were not represented with a statisti- cally significant number of specimens.

Of the 73 hashish exhibits from nine countries, 68 were included in the database: A recent report indicated lack of ho- mogeneity in bars of compressed Cannabis resin hashish; ref. Extraction Each marijuana sample was first manicured so that the material became a homo- geneous mixture of leaf particles with no seeds or stems. The extraction solution was methanol and chloroform mixed in a ratio of 9: Phenan- threne served as an internal standard, a chemical not naturally present in cannabis but appearing as an isolated peak in the chromatograms for use as both a retention time marker and a reference for the calculation of the quantities of the peaks of interest.

The tube containing the sample and extraction solution was placed in an ultrasonic water bath for 15 minutes to break the plant tissue and allow soluble chemicals of Cannabis to be dissolved in the extraction solution. The tube was then spun in a cen- trifuge to force the plant particles to the bottom so that the resulting clear green solu- tion could then be transferred to a screw-capped vial without disturbing the sediment.

Hashish samples were prepared very similarly, with the exception that a Because hashish in such small quantities was 58 ElSohly et al. Mass spectral data was acquired within the range of amu at a rate of 0. After a sample was injected, data acquisition automatically started after 5 minutes to allow the solvent to pass before peaks of interest began to elute. Although the GC oven cycled back to the starting temperature after 62 minutes, data acquisition ended 54 minutes into the run after the last peak was recorded.

To ensure that the instrument was operating properly, a QC solution was injected after every nine test samples, and the QC chromatogram was examined for integrity. A mixture of terpenes, cannabinoids, hydrocarbons, and the internal standard was selected for QC to provide a reference of known peaks throughout the entire time of the run. Injector and col- umn maintenance was performed on a routine schedule to prevent any "memory effect" resulting from repeated injections, but no blanks were run between samples.

Mahmoud A Elsohly (Author of Marijuana and the Cannabinoids. Forensic Science and Medicine.)

Each test sample chromatogram was evaluated for acceptability before data analy- sis. If the chromatogram exhibited an unusual baseline or low sensitivity, the injection was repeated. The area under each peak was measured using ITDS software in the manual mode rather than the automatic mode so that the operator could evaluate each of the peaks plus the internal standard peak for proper peak shape and to ensure correct identity assignments as well.

Quantitative values of each peak were automati- cally calculated by determining the ratio of the area of the peak to that of the internal standard within the same chromatogram and comparing that ratio to that of a standard- ized calibration file. To analyze the data using the power of Pirouette, first the database of all mari- juana exhibits from the four countries and two states was used to construct a model of the six classes of fingerprints.

The data within the model were examined to ascertain similarities and differences of the location classes. Having appropriate models for comparison, the remainder of the proposed data analysis experiments were conducted, constructing additional models as neces- sary. All results were based on the a K-nearest-neighbor classification method Results of the Phase II Study 6. Similarities Within the Model Within the comparison of the broad classes of domestic vs foreign, all foreign exhibits were correctly classified.

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Only one domestic exhibit, a Hawaiian specimen, was misclassified. When the domestic exhibits were compared with the four foreign countries, the single exhibit discrepant in the domestic vs foreign test was again misclassified, being indicated to be from Jamaica. The number of misclassifications increased when the exhibits representing indi- vidual states were tested within a six-region model.

The majority of misclassified Hawaiian specimens again looked Jamaican. All Californian exhibits were correctly identified. Identification of Unknowns Satisfied that the phase II fingerprint data were valid when samples included in the model were tested, the system was challenged with specimens not included in the model. This evaluation was repeated five times, each time removing different exhibits and testing those against each new model. The results are summarized in Table 2, which shows correct classifi- cations vs total unknowns for each of the five rounds of evaluation and the totals of the individual rounds.

Although the results certainly ascertained the viability of the fingerprint system, we were still concerned about the source of the errors. To investigate the causes of the erroneous predictions, we closely examined the data from a different viewpoint. Pre- sented in Table 3 is a matrix chart of the misclassified exhibits showing which loca- tions fit the fingerprint more closely than the model of its actual origin.

It was evident that exhibits within certain regions tended to be misclassified more often than those from other locations, but those trends would likely be tempered in a database com- posed of more exhibits. Although the distinctive fingerprints of the Hawaiian mari- juana improved the classification rates of those exhibits, those differences also weakened the domestic model. The majority of California exhibits were known to have been grown in the northern part of the state, but the single exhibit from southern 60 Table 2 Correct Classifications of Unknowns ElSohly et al.

Indoor vs Outdoor For year-round production and to avoid routine surveillance, marijuana growers in the United States increasingly prefer to nurture their plants indoors out of sight. An added benefit of indoor horticulture is that the grower, rather than Mother Nature, controls the environment and can provide ideal lighting and temperature conditions as well as exact levels of water and nutrients.

Not surprisingly, therefore, the fingerprints of plants grown indoors are significantly dissimilar to those of outdoor plants. A model consisting of three classes — outdoors in the ground, outdoors in pots commercial potting soil , and indoors commercial potting soil — was constructed from fingerprints of Jamaican plants grown in the UM facilities.

All of those speci- mens were then tested against that model. The only misclassifications were within the outdoor group, as those plants with roots in the earth were sometimes confused with those in pots, a trend that indicates that light and temperature may influence the chemical profiles more than soil conditions. Daughter Plants Grown in a Different Region A most interesting experiment was the test to see how the fingerprints of plants from foreign seeds cultivated in Mississippi would fare in the system.

Fingerprints of the resulting plants were tested against the model constructed from all of the phase II exhibits. The high rate of misclassification supported original predictions that, although genetic relationships are reflected in the fingerprints, the environment has a greater effect on the chemical profiles. Age and Sex The original experimental design of the fingerprint study required that all speci- mens included in the database be from mature female plants, the type of marijuana commonly trafficked in the illicit market.

To determine if those criteria were actually necessary was the intention of the exercise based on the age and sex of plants. Experi- mentally grown specimens of 8 and 12 weeks of age were considered immature, whereas those 16, 20, and 25 weeks of age were included in the mature class. An equal number of both sexes were included. It appears from these data that the sex of the plant did not contribute as much to the fingerprint as did the age of the plant. The maturity of the plants, although not of great interest to the intelligence community, was definitely a factor in the accuracy of the fingerprint system.

Our experience analyzing confiscated marijuana for more than 30 years shows that the majority of the samples were from mature plants based on the physical examination of the samples. The only exception is those samples seized at the growing locations before time to harvest. Storage Conditions To determine the effect of storage conditions on chemical fingerprints, sets of data were compiled into four models, each having one constant condition and one variant condition of the two factors: When you click on a Sponsored Product ad, you will be taken to an Amazon detail page where you can learn more about the product and purchase it.

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