Skip to main content
Book cover

Marijuana and the Cannabinoids pp 17–49Cite as

Chemistry and Analysis of Phytocannabinoids and Other Cannabis Constituents

  • Chapter

Part of the Forensic Science And Medicine book series (FSM)

Abstract

The Cannabis plant and its products consist of an enormous variety of chemicals. Some of the 483 compounds identified are unique to Cannabis, for example, the more than 60 cannabinoids, whereas the terpenes, with about 140 members forming the most abundant class, are widespread in the plant kingdom. The term “cannabinoids” [note: “ ” represents a group of C21 terpenophenolic compounds found until now uniquely in Cannabis sativa L. (1). As a consequence of the development of synthetic cannabinoids (e.g., nabilone [2], HU-211 [dexanabinol; ref. (3), or ajulemic acid [CT-3; ref. 4]) and the discovery of the chemically different endogenous cannabinoid receptor ligands (“endocannabinoids,” e.g., anandamide, 2-arachidonoylglycerol) (5,6), the term ’“phytocannabinoids’” was proposed for these particular Cannabis constituents (7).

Keywords

  • High Pressure Liquid Chromatography
  • Cannabis Sativa
  • Cannabis Plant
  • Cannabis Product
  • Cannabis Resin

These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

This is a preview of subscription content, access via your institution.

Chapter
USD   29.95
Price excludes VAT (USA)
  • DOI: 10.1007/978-1-59259-947-9_2
  • Chapter length: 33 pages
  • Instant PDF download
  • Readable on all devices
  • Own it forever
  • Exclusive offer for individuals only
  • Tax calculation will be finalised during checkout
eBook
USD   149.00
Price excludes VAT (USA)
  • ISBN: 978-1-59259-947-9
  • Instant PDF download
  • Readable on all devices
  • Own it forever
  • Exclusive offer for individuals only
  • Tax calculation will be finalised during checkout
Softcover Book
USD   199.99
Price excludes VAT (USA)
Hardcover Book
USD   279.99
Price excludes VAT (USA)
Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Mechoulam, R. and Gaoni, Y. (1967) Recent advances in the chemistry of hashish. Fortschr. Chem. Org. Naturst. 25, 175–213.

    PubMed  CAS  Google Scholar 

  2. Ward, A. and Holmes, B. (1985) Nabilone. A preliminary review of its pharmacological properties and therapeutic use. Drugs 30, 127–144.

    PubMed  CAS  Google Scholar 

  3. Mechoulam, R., Lander, N., Breuer, A., and Zahalka, J. (1990) Synthesis of the individual, pharmacologically distinct, enantiomers of a tetrahydrocannabinol derivative. Tetrahedron Asymmetry 1, 315–318.

    CrossRef  CAS  Google Scholar 

  4. Burstein, S. H., Audette, C. A., Breuer, A., et al. (1992) Synthetic nonpsychotropic cannabinoids with potent antiinflammatory, analgesic, and leukocyte antiadhesion activities. J. Med. Chem. 35, 3135–3141.

    CrossRef  PubMed  CAS  Google Scholar 

  5. Di Marzo, V. and Fontana, A. (1995) Anandamide, an endogenous cannabinomimetic eicosanoid:’ killing two birds with one stone’. Prostaglandins Leukot. Essent. Fatty Acids 53, 1–11.

    CrossRef  PubMed  Google Scholar 

  6. Devane, W. A., Hanus, L., Breuer, A., et al. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258, 1946–1949.

    CrossRef  PubMed  CAS  Google Scholar 

  7. Pate, D. (1999) Anandamide structure-activity relationships and mechanisms of action on intraocular pressure in the normotensive rabbit model, PhD thesis, University of Kuopio, Kuopio, Finland.

    Google Scholar 

  8. Turner, C. E., Elsohly, M. A., and Boeren, E. G. (1980) Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J. Nat. Prod. 43, 169–234.

    CrossRef  PubMed  CAS  Google Scholar 

  9. Ross, S. A. and ElSohly, M. A. (1995) Constituents of Cannabis sativa L. XXVIII-A review of the natural constituents: 1980-1994. Zagazig J. Pharm. Sci. 4, 1–10.

    CAS  Google Scholar 

  10. ElSohly, M. (2002) Chemical constituents of Cannabis, in Cannabis and cannabinoids— Pharmacology, Toxicology and Therapeutic Potential (Grotenhermen, F. and Russo, E., eds.), Haworth Press, New York, pp. 27–36.

    Google Scholar 

  11. Gaoni, Y. and Mechoulam, R. (1964) The structure and synthesis of cannabigerol, a new hashish constituent, in Proc. Chem. Soc., London, p. 82.

    Google Scholar 

  12. Shoyama, Y., Yagi, M., Nishioka, I., and Yamauchi, T. (1975) Biosynthesis of cannab-inoid acids. Phytochemistry 14, 2189–2192.

    CrossRef  CAS  Google Scholar 

  13. Adams, R., Hunt, M., and Clark, J. (1940) Structure of cannabidiol, a product isolated from the marihuana extract of Minnesota wild hemp. I. J. Am. Chem. Soc. 62, 196–199.

    CrossRef  CAS  Google Scholar 

  14. Mechoulam, R. and Shvo, Y. (1963) Hashish—I. The structure of cannabidiol. Tetrahedron 19, 2073–2078.

    CrossRef  CAS  Google Scholar 

  15. Wollner, H., Matchett, J., Levine, J., and Loewe, S. (1942) Isolation of a physiologically active tetrahydrocannabinol from Cannabis sativa resin. J. Am. Chem. Soc. 64, 26–29.

    CrossRef  CAS  Google Scholar 

  16. Gaoni, Y. and Mechoulam, R. (1964) Isolation, structure and partial synthesis of an active constituent of hashish. J. Am. Chem. Soc. 86, 1646–1647.

    CrossRef  CAS  Google Scholar 

  17. Wood, T., Spivey, W., and Easterfield, T. (1896) XL. Charas. The resin of Indian hemp. J. Chem. Soc. 69, 539.

    CAS  Google Scholar 

  18. Adams, R., Baker, B., and Wearn, R. (1940) Structure of cannabinol III. Synthesis of cannabinol, 1-hydroxy-3-n-amyl-6,6,9-trimethyl-6-dibenzopyran. J. Am. Chem. Soc. 62, 2204–2207.

    CrossRef  CAS  Google Scholar 

  19. ElSohly, M., Ross, S., Mehmedic, Z., Arafat, R., Yi, B., and Banahan, B.F., 3rd (2000) Potency trends of delta-9-THC and other cannabinoids in confiscated marijuana from 1980-1997. J. Forens. Sci. 45, 24–30.

    CAS  Google Scholar 

  20. Brenneisen, R. (1986) The cannabinoid content in Cannabis products confiscated in Switzerland. Arch. Kriminol. 177, 95–104.

    CAS  Google Scholar 

  21. Brenneisen, R. and Meyer, P. Swiss Cannabis Profiling Project, University of Bern and Swiss Federal Office of Public Health (unpublished data).

    Google Scholar 

  22. Miller Coyle, H., Palmbach, T., Juliano, N., Ladd, C., and Lee, H. C. (2003) An overview of DNA methods for the identification and individualization of marijuana. Croat. Med. J. 44, 315–321.

    PubMed  Google Scholar 

  23. ElSohly, M. (2003) Practical challenges to positive drug tests for marijuana. Clin. Chem. 49, 1037–1038.

    CrossRef  PubMed  CAS  Google Scholar 

  24. Leson, G., Pless, P., Grotenhermen, F., Kalant, H., and ElSohly, M. A. (2001) Evaluating the impact of hemp food consumption on workplace drug tests. J. Anal. Toxicol. 25, 691–698.

    PubMed  CAS  Google Scholar 

  25. Ross, S. A., Mehmedic, Z., Murphy, T. P., and Elsohly, M. A. (2000) GC-MS analysis of the total delta9-THC content of both drug-and fiber-type Cannabis seeds. J. Anal. Toxicol. 24, 715–717.

    PubMed  CAS  Google Scholar 

  26. Bosy, T. Z. and Cole, K. A. (2000) Consumption and quantitation of delta-9-tetrahydrocan-nabinol in commercially available hemp seed oil products. J. Anal. Toxicol. 24, 562–6.

    PubMed  CAS  Google Scholar 

  27. Mediavilla, V., Derungs, R., Känzig, A., and Mägert, A. (1997) Qualität von Hanfsamenöl aus der Schweiz. Agrarforschung 4, 449–451.

    Google Scholar 

  28. Lehmann, T., Sager, F., and Brenneisen, R. (1997) Excretion of cannabinoids in urine after ingestion of Cannabis seed oil. J. Anal. Toxicol. 21, 373–375.

    PubMed  CAS  Google Scholar 

  29. Mediavilla, V. and Steinemann, S. (1997) Essential oil of Cannabis sativa L. strains. J. Int. Hemp Assoc. 4, 80–82.

    Google Scholar 

  30. Meier, C. and Mediavilla, V. (1998) Factors influencing the yield and the quality of hemp (Cannabis sativa L.) essential oil. J. Int. Hemp Assoc. 5, 16–20.

    Google Scholar 

  31. Lehmann, T. (1995) Chemical profiling of Cannabis sativa L., PhD thesis, University of Bern, Dep. of Pharmaceutical Sciences, Bern, Switzerland.

    Google Scholar 

  32. Ross, S.A. and ElSohly, M. A. (1996) The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J. Nat. Prod. 59, 49–51.

    CrossRef  PubMed  CAS  Google Scholar 

  33. Novak, J., Zitterl-Eglseer, K., Deans, S. G., and Franz, C. M. (2001) Essential oils of different cultivars of Cannabis sativa L. and their antimicrobial activity. Flavour Fragr. J. 16, 259–262.

    CrossRef  CAS  Google Scholar 

  34. McPartland, J. M. and Russo, E. B. (2001) Cannabis and Cannabis extracts: greater than the sum of their parts? J. Cann. Therap. 1, 103–132.

    CrossRef  CAS  Google Scholar 

  35. Hendriks, H., Malingré, T. M., Batterman, S., and Bos, R. (1977) Alkanes of the essential oil of Cannabis sativa. Phytochemistry 16, 719–721.

    CrossRef  CAS  Google Scholar 

  36. McPartland, J. and Mediavilla, V. (2002) Noncannabinoid components, in Cannabis and Cannabinoids-Pharmacology, Toxicology, and Therapeutic Potential (Grotenhermen, F., and Russo, E., eds.), Haworth Press, New York, pp. 401–409.

    Google Scholar 

  37. Vanhoenacker, G., Van Rompaey, P., De Keukeleire, D., and Sandra, P. (2002) Chemo-taxonomic features associated with flavonoids of cannabinoid-free Cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.). Nat. Prod. Lett. 16, 57–63.

    CrossRef  PubMed  CAS  Google Scholar 

  38. Barrett, M. L., Scutt, A. M., and Evans, F. J. (1986) Cannflavin A and B, prenylated flavones from Cannabis sativa L. Experientia 42, 452–453.

    CrossRef  PubMed  CAS  Google Scholar 

  39. Barrett, M. L., Gordon, D., and Evans, F. J. (1985) Isolation from Cannabis sativa L. of cannflavin-a novel inhibitor of prostaglandin production. Biochem. Pharmacol. 34, 2019–2024.

    CrossRef  PubMed  CAS  Google Scholar 

  40. Leson, G., Pless, P., and Roulac, J. (1999) Hemp Foods and Oils for Health, Hemptech, Sebastopol, CA.

    Google Scholar 

  41. Ross, S., ElSohly, H., ElKashoury, E., and ElSohly, M. (1996) Fatty acids of Cannabis seeds. Phytochem. Anal. 7, 279–283.

    CrossRef  CAS  Google Scholar 

  42. Grotenhermen, F. (2002) Effects of Cannabis and the cannabinoids, in Cannabis and Cannabinoids-Pharmacology, Toxicology, and Therapeutic Potential (Grotenhermen, F. and Russo, E., eds.), Haworth Press, New York, pp. 55–65.

    Google Scholar 

  43. Grotenhermen, F. and Russo, E. (eds.) (2002) Cannabis and Cannabinoids-Pharmacology, Toxicology, and Therapeutic Potential, Haworth Press, New York, p. 439.

    Google Scholar 

  44. Iversen, L. (2003) Cannabis and the brain. Brain 126, 1252–1270.

    CrossRef  PubMed  Google Scholar 

  45. Croxford, J. L. (2003) Therapeutic potential of cannabinoids in CNS disease. CNS Drugs 17, 179–202.

    CrossRef  PubMed  CAS  Google Scholar 

  46. Kumar, R., Chambers, W., and Pertwee, R. G. (2001) Pharmacological actions and therapeutic uses of Cannabis and cannabinoids. Anaesthesia 56, 1059–68.

    CrossRef  PubMed  CAS  Google Scholar 

  47. Hirst, R. A., Lambert, D. G., and Notcutt, W. G. (1998) Pharmacology and potential therapeutic uses of Cannabis. Br. J. Anaesth. 81, 77–84.

    PubMed  CAS  Google Scholar 

  48. Ashton, C. H. (1999) Adverse effects of Cannabis and cannabinoids. Br. J. Anaesth. 83, 637–49.

    PubMed  CAS  Google Scholar 

  49. Williamson, E. M. and Evans, F. J. (2000) Cannabinoids in clinical practice. Drugs 60, 1303–1314.

    CrossRef  PubMed  CAS  Google Scholar 

  50. Campbell, F. A., Tramèr, M. R., Carroll, D., Reynolds, D. J., Moore, R. A., and McQuay, H. J. (2001) Are cannabinoids an effective and safe treatment option in the management of pain? A qualitative systematic review. Br. Med. J. 323, 13–16.

    CrossRef  CAS  Google Scholar 

  51. .Tramèr, M. R., Carroll, D., Campbell, F. A., Reynolds, D. J., Moore, R. A., and McQuay, H. J. (2001) Cannabinoids for control of chemotherapy induced nausea and vomiting: quantitative systematic review. Br. Med. J. 323, 16–21.

    CrossRef  Google Scholar 

  52. Walker, J. M. and Huang, S. M. (2002) Cannabinoid analgesia. Pharmacol. Ther. 95, 127–135.

    CrossRef  PubMed  CAS  Google Scholar 

  53. Voth, E. A. and Schwartz, R. H. (1997) Medicinal applications of delta-9-tetrahydrocan-nabinol and marijuana. Ann. Int. Med. 126, 791–798.

    PubMed  CAS  Google Scholar 

  54. McPartland, J. M. and Pruitt, P. L. (1999) Side effects of pharmaceuticals not elicited by comparable herbal medicines: the case of tetrahydrocannabinol and marijuana. Altern. Ther. 5, 57–62.

    CrossRef  CAS  Google Scholar 

  55. Wachtel, S. R., ElSohly, M. A., Ross, S. A., Ambre, J., and de Wit, H. (2002) Comparison of the subjective effects of delta-9-tetrahydrocannabinol and marijuana in humans. Psychopharmacology 161, 331–339.

    CrossRef  PubMed  CAS  Google Scholar 

  56. Hart, C. L., Ward, A. S., Haney, M., Comer, S. D., Foltin, R. W., and Fischman, M. W. (2002) Comparison of smoked marijuana and oral Delta(9)-tetrahydrocannabinol in humans. Psychopharmacology 164, 407–415.

    CrossRef  PubMed  CAS  Google Scholar 

  57. Mechoulam, R., Parker, L. A., and Gallily, R. (2002) Cannabidiol: an overview of some pharmacological aspects. J. Clin. Pharmacol. 42, 11S–19S.

    PubMed  CAS  Google Scholar 

  58. Consroe, P. (1998) Brain cannabinoid systems as targets for the therapy of neurological disorders. Neurobiol. Dis. 5, 534–551.

    CrossRef  PubMed  CAS  Google Scholar 

  59. Bornheim, L. M., Kim, K. Y., Li, J., Perotti, B. Y., and Benet, L. Z. (1995) Effect of cannabidiol pretreatment on the kinetics of tetrahydrocannabinol metabolites in mouse brain. Drug Metab. Dispos. 23, 825–831.

    PubMed  CAS  Google Scholar 

  60. Meschler, J. P. and Howlett, A. C. (1999) Thujone exhibits low affinity for cannabinoid receptors but fails to evoke cannabimimetic responses. Pharmacol. Biochem. Behav. 62, 473–480.

    CrossRef  PubMed  CAS  Google Scholar 

  61. Russo, E. (2001) Hemp for headache: an in-depth historical and scientific review of can-nabis in migraine treatment. J. Cann. Ther. 1, 21–92.

    CrossRef  Google Scholar 

  62. Salgueiro, J. B., Ardenghi, P., Dias, M., Ferreira, M. B., Izquierdo, I., and Medina, J. H. (1997) Anxiolytic natural and synthetic flavonoid ligands of the central benzodiazepine receptor have no effect on memory tasks in rats. Pharmacol. Biochem. Behav. 58, 887–891.

    CrossRef  PubMed  CAS  Google Scholar 

  63. Mitosinka, G. T., Thornton, J. I., and Hayes, T. L. (1972) The examination of cystolithic hairs of Cannabis and other plants by means of the scanning electron microscope. J. Forens. Sci Soc. 12, 521–529.

    CAS  Google Scholar 

  64. Thornton, J. I. and Nakamura, G. R. (1972) The identification of marijuana. J. Forens. Sci. Soc. 12, 461–519.

    CAS  Google Scholar 

  65. Gigliano, G. (2001) Cannabis sativa L.—botanical problems and molecular approaches in forensic investigations. Forens. Sci. Rev. 13, 2–17.

    Google Scholar 

  66. .Stearn, W. T. (1970) The Cannabis plant: botanical characteristics, in The Botany & Chemistry of Cannabis (Joyce, C. and Curry, S., eds.), J. & A. Churchill, London, p. 1.

    Google Scholar 

  67. Nordal, A. (1970) Microscopic detection of Cannabis in the pure state and in semi-combusted residues, in The Botany & Chemistry of Cannabis (Joyce, C. and Curry, S., eds.), J. & A. Churchill, London, pp. 61–68.

    Google Scholar 

  68. Petri, G., Oroszlan, P., and Fridvalszky, L. (1988) Histochemical detection of hemp tri-chomes and their correlation with the THC content. Acta Biol. Hung. 39, 59–73.

    PubMed  CAS  Google Scholar 

  69. Bruni, A., Barni Comparini, I., and Menziani Andreoli, E. (1983) A histofluorescent procedure for identifying marijuana cannabinoids. Experientia 39, 886–888.

    CrossRef  PubMed  CAS  Google Scholar 

  70. United Nations (1987) Recommended Methods for Testing Cannabis, ST/NAR/8, Division of Narcotic Drugs, United Nations, New York.

    Google Scholar 

  71. Bailey, K. (1979) The value of the Duquenois test for Cannabis-a survey. J. Forens. Sci. 24, 817–841.

    CAS  Google Scholar 

  72. Butler, W. (1962) Duquenois-Levine test for marijuana. J. Assoc. Off. Anal. Chem. 45, 597–600.

    CAS  Google Scholar 

  73. Tewari, S. N. and Sharma, J. D. (1982) Spot tests for Cannabis materials. Bull. Narc. 34, 109–112.

    PubMed  CAS  Google Scholar 

  74. Pitt, C. G., Hendron, R. W., and Hsia, R. S. (1972) The specificity of the Duquenois color test for marihuana and hashish. J. Forens. Sci. 17, 693–700.

    CAS  Google Scholar 

  75. Mali, B. D. and Parulekar, P. P. (1988) Diazotized dapsone as a reagent for the detection of cannabinoids on thin-layer chromatographic plates. J. Chromatogr. 457, 383–386.

    CrossRef  PubMed  CAS  Google Scholar 

  76. Baker, P. B., Gough, T. A., and Taylor, B. J. (1980) Illicitly imported Cannabis products: some physical and chemical features indicative of their origin. Bull. Narc. 32, 31–40.

    PubMed  CAS  Google Scholar 

  77. Debruyne, D., Albessard, F., Bigot, M. C., and Moulin, M. (1994) Comparison of three advanced chromatographic techniques for Cannabis identification. Bull. Narc. 46, 109–121.

    PubMed  CAS  Google Scholar 

  78. Pothier, J., Galand, N., and Viel, C. (1992) Rapid characterization of stupefacient and toxic substances by pressurized thin-layer chromatography. J. Toxicol. Clin. Exp. 12, 495–501.

    PubMed  CAS  Google Scholar 

  79. Oroszlan, P., Verzar-Petri, G., Mincsovics, E., and Szekely, T. (1987) Separation, quantitation and isolation of cannabinoids from Cannabis sativa L. by overpressured layer chromatography. J. Chromatogr. 388, 217–224.

    CrossRef  PubMed  CAS  Google Scholar 

  80. Ferioli, V., Rustichelli, C., Pavesi, G., and Gamberini, G. (2000) Analytical characterisation of hashish samples. Chromatographia 52, 39–44.

    CrossRef  CAS  Google Scholar 

  81. Debruyne, D., Moulin, M., Bigot, M. C., and Camsonne, R. (1981) Identification and differentiation of resinous Cannabis and textile Cannabis: combined use of HPLC and high-resolution GLC. Bull. Narc. 33, 49–58.

    PubMed  CAS  Google Scholar 

  82. Tsatsakis, A. M., Tutudaki, M., Stiakakis, I., Dimopoulou, M., Tzatzarakis, M., and Michalodimitrakis, M. (2000) Characterisation of Cannabis plants phenotypes from illegal cultivations in Crete. Boll. Chim. Farm. 139, 140–145.

    PubMed  CAS  Google Scholar 

  83. Ross, S. A. and ElSohly, M. A. (1996) The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J. Nat. Prod. 59, 49–51.

    CrossRef  PubMed  CAS  Google Scholar 

  84. Barni Comparini, I. and Centini, F. (1983) Packed column chromatography, high-resolution gas-chromatography and high pressure liquid chromatography in comparison for the analysis of Cannabis constituents. Forens. Sci. Int. 21, 129–137.

    CrossRef  CAS  Google Scholar 

  85. Harvey, D. J. (1990) Stability of cannabinoids in dried samples of Cannabis dating from around 1896-1905. J. Ethnopharmacol. 28, 117–128.

    CrossRef  PubMed  CAS  Google Scholar 

  86. Turner, C. E., Bouwsma, O. J., Billets, S., and Elsohly, M. A. (1980) Constituents of Cannabis sativa L. XVIII-Electron voltage selected ion monitoring study of cannabinoids. Biomed. Mass Spectrom. 7, 247–256.

    CrossRef  PubMed  CAS  Google Scholar 

  87. Brenneisen, R. and ElSohly, M. A. (1988) Chromatographic and spectroscopic profiles of Cannabis of different origins: PartI. J. Forens. Sci. 33, 1385–1404.

    CAS  Google Scholar 

  88. Bosy, T. Z. and Cole, K. A. (2000) Consumption and quantitation of delta-9-tetrahydrocan-nabinol in commercially available hemp seed oil products. J. Anal. Toxicol. 24, 562–566.

    PubMed  CAS  Google Scholar 

  89. Lercker, G., Bocci, F., Frega, N., and Bortolomeazzi, R. (1992) Cannabinoid acids analysis. Farmaco 47, 367–378.

    PubMed  CAS  Google Scholar 

  90. Vree, T. B. (1977) Mass spectrometry of cannabinoids. J. Pharm. Sci. 66, 1444–1450.

    CrossRef  PubMed  CAS  Google Scholar 

  91. Novotny, M., Lee, M. L., Low, C. E., and Raymond, A. (1976) Analysis of marijuana samples from different origins by high-resolution gas-liquid chromatography for forensic application. Anal. Chem. 48, 24–29.

    CrossRef  PubMed  CAS  Google Scholar 

  92. Raharjo, T. J. and Verpoorte, R. (2004) Methods for the analysis of cannabinoids in biological materials: a review. Phytochem. Anal. 15, 79–94.

    CrossRef  PubMed  CAS  Google Scholar 

  93. Lehmann, T. and Brenneisen, R. (1995) High performance liquid chromatographic profiling of Cannabis products. J. Liq. Chromatogr. 18, 689–700.

    CrossRef  CAS  Google Scholar 

  94. Barni Comparini, I. and Centini, F. (1983) Packed column chromatography, high-resolution gas-chromatography and high pressure liquid chromatography in comparison for the analysis of Cannabis constituents. Forens. Sci. Int. 21, 129–37.

    CrossRef  CAS  Google Scholar 

  95. Zoller, O., Rhyn, P., and Zimmerli, B. (2000) High-performance liquid chromatographic determination of delta9-tetrahydrocannabinol and the corresponding acid in hemp containing foods with special regard to the fluorescence properties of delta9-tetrahydrocan-nabinol. J. Chromatogr. A 872, 101–110.

    CrossRef  PubMed  CAS  Google Scholar 

  96. Baker, P. B., Gough, T. A., and Wagstaffe, P. J. (1983) Determination of the distribution of cannabinoids in Cannabis resin from Morocco using high-performance liquid chroma-tography. Part II. J. Anal. Toxicol. 7, 7–10.

    PubMed  CAS  Google Scholar 

  97. Baker, P. B., Taylor, B. J., and Gough, T. A. (1981) The tetrahydrocannabinol and tetrahydrocannabinolic acid content of Cannabis products. J. Pharm. Pharmacol. 33, 369–372.

    PubMed  CAS  Google Scholar 

  98. McDonald, P. A. and Gough, T. A. (1984) Determination of the distribution of cannabinoids in Cannabis resin from the Lebanon using HPLC. Part III. J. Chromatogr. Sci. 22, 282–284.

    PubMed  CAS  Google Scholar 

  99. Brenneisen, R. (1984) Psychotropic drugs. II. Determination of cannabinoids in Cannabis sativa L. and in Cannabis products with high pressure liquid chromatography (HPLC). Pharm. Acta Helv. 59, 247–259.

    PubMed  CAS  Google Scholar 

  100. Rustichelli, C., Ferioli, V., Baraldi, M., Zanoli, P., and Gamberini, G. (1998) Analysis of cannabinoids in fiber hemp plant varieties (Cannabis sativa) by high-performance liquid chromatography. Chromatographia 8, 215–222.

    CrossRef  Google Scholar 

  101. Baker, P. B., Fowler, R., Bagon, K. R., and Gough, T. A. (1980) Determination of the distribution of cannabinoids in Cannabis resin using high performance liquid chromatography. J. Anal. Toxicol. 4, 145–152.

    PubMed  CAS  Google Scholar 

  102. Nakahara, Y. and Tanaka, K. (1988) Studies on discrimination of confiscated Cannabis products by high performance liquid chromatography with electrochemical detector. Eisei Shikenjo Hokoku, Bulletin of National Institute of Hygenic Sciences, pp.11–18.

    Google Scholar 

  103. Rustichelli, C., Ferioli, V., Vezzalini, F., Rossi, M. C., and Gamberini, G. (1996) Simultaneous separation and identification of hashish constituents by coupled liquid chroma-tography-mass spectrometry (HPLC-MS). Chromatographia 43, 129–134.

    CrossRef  CAS  Google Scholar 

  104. Lurie, I. S., Meyers, R. P., and Conver, T. S. (1998) Capillary electrochromatography of cannabinoids. Anal. Chem. 70, 3255–3260.

    CrossRef  PubMed  CAS  Google Scholar 

  105. Backstrom, B., Cole, M. D., Carrott, M. J., Jones, D. C., Davidson, G., and Coleman, K. (1997) A preliminary study of the analysis of Cannabis by supercritical fluid chromatography with atmospheric pressure chemical ionisation mass spectroscopic detection. Sci. Justice 37, 91–97.

    PubMed  CAS  Google Scholar 

  106. Miller Coyle, H., Ladd, C., Palmbach, T., and Lee, H. C. (2001) The green revolution: botanical contributions to forensics and drug enforcement. Croat. Med. J. 42, 340–345.

    PubMed  CAS  Google Scholar 

  107. Miller Coyle, H., Palmbach, T., Juliano, N., Ladd, C., and Lee, H. C. (2003) An overview of DNA methods for the identification and individualization of marijuana. Croat. Med. J. 44, 315–321.

    PubMed  Google Scholar 

  108. Cole, M. D. and Linacre, A. M. T. (2002) The identification of controlled plant drugs using phytochemistry and DNA. Curr. Topics Phytochem. 5, 129–140.

    CAS  Google Scholar 

  109. Linacre, A. and Thorpe, J. (1998) Detection and identification of Cannabis by DNA. Forens. Sci. Int. 91, 71–76.

    CrossRef  CAS  Google Scholar 

  110. Siniscalco Gigliano, G., Caputo, P., and Cozzolino, S. (1997) Ribosomal DNA analysis as a tool for the identification of Cannabis sativa L. specimens of forensic interest. Sci. Justice 37, 171–174.

    PubMed  CAS  Google Scholar 

  111. Gillan, R., Cole, M., Linacre, A., Thorpe, J. W., and Watson, N. D. (1995) Comparison of Cannabis sativa by random amplification of polymorphic DNA (RAPD) and HPLC of cannabinoids: a preliminary study. Sci. Justice 35, 169–177.

    PubMed  CAS  Google Scholar 

  112. Miller Coyle, H., Sutler, G., Abrams, S., et al. (2003) A simple DNA extraction method for Marijuana samples used in amplified fragment length polymorphism (AFLP) analysis. J. Forens. Sci. 48, 343–347.

    Google Scholar 

  113. Hsieh, H. M., Hou, R. J., Tsai, L. C., et al. (2003) A highly polymorphic STR locus in Cannabis sativa. Forens. Sci. Int. 131, 53–58.

    CrossRef  CAS  Google Scholar 

  114. Gilmore, S., Peakall, R., and Robertson, J. (2003) Short tandem repeat (STR) DNA markers are hypervariable and informative in Cannabis sativa: implications for forensic investigations. Forens. Sci. Int. 131, 65–74.

    CrossRef  CAS  Google Scholar 

  115. Kojoma, M., Iida, O., Makino, Y., Sekita, S., and Satake, M. (2002) DNA fingerprinting of Cannabis sativa using inter-simple sequence repeat (ISSR) amplification. Planta Med. 68, 60–63.

    CrossRef  PubMed  CAS  Google Scholar 

  116. Gigliano, G. (1998) Identification of Cannabis sativa L. (Cannabaceae) using restriction profiles of the Internal Transcribed Spacer II (ITS2). Sci. Justice 38, 225–230.

    CrossRef  PubMed  CAS  Google Scholar 

  117. Alghanim, H. J. and Almirall, J. R. (2003) Development of micro satellite markers in Cannabis sativa for DNA typing and genetic relatedness analyses. Anal. Bioanal. Chem. 376, 1225–1233.

    CrossRef  PubMed  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Clinical Research, Laboratory for Phytopharmacology, Bioanalytics and Pharmacokinetics, University of Bern, Bern, Switzerland

    Rudolf Brenneisen PhD

Authors
  1. Rudolf Brenneisen PhD
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. The School of Pharmacy, The University of Mississippi; ElSohly Laboratories Inc., Oxford, MS

    Mahmoud A. ElSohly PhD

Rights and permissions

Reprints and Permissions

Copyright information

© 2007 Humana Press Inc., Totowa, New Jersey

About this chapter

Cite this chapter

Brenneisen, R. (2007). Chemistry and Analysis of Phytocannabinoids and Other Cannabis Constituents . In: ElSohly, M.A. (eds) Marijuana and the Cannabinoids. Forensic Science And Medicine. Humana Press. https://doi.org/10.1007/978-1-59259-947-9_2

Download citation

  • DOI: https://doi.org/10.1007/978-1-59259-947-9_2

  • Publisher Name: Humana Press

  • Print ISBN: 978-1-58829-456-2

  • Online ISBN: 978-1-59259-947-9

  • eBook Packages: MedicineMedicine (R0)