Skip to main content
SpringerLink
Log in

Chemistry of Cannabis

  • Chapter
Book cover Psychotropic Agents

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 55 / 3))

Abstract

The aim of this chapter is to present a short summary of cannabinoid1 chemistry with emphasis on those aspects which have pharmacological relevance. A comprehensive chemical review is beyond the scope of this handbook. Since 1964, when the active principle of cannabis, Δ 1-tetrahydrocannabinol (Δ 1-THC), was identified (Gaoni and Mechoulam, 1964a), nearly 5,000 scientific articles on cannabis, Δ 1-THC and other cannabinoids have appeared; approximately 1,000 of these articles are chemically oriented. For this reason alone the present review will have to be selective.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Adams, R., Baker, B.R., Wearn, R.B.: Synthesis of cannabinol, l-hydroxy-3n-amyl-6,6,9- trimethyl-6-dibenzopyran. J. Am. Chem. Soc. 62, 2204–2207 (1940)

    CAS  Google Scholar 

  • Agurell, S., Gustafsson, B., Holmstedt, B., Leander, K., Lindgren, J.-E., Nilsson, I., Sandberg, F., Asberg, M.: Quantitation of Δ 1-THC in plasma from cannabis smokers. J. Pharm. Pharmacol. 25, 554–558 (1973)

    PubMed  CAS  Google Scholar 

  • Archer, R.A.: The cannabinoids: Therapeutic potential. Ann. Rep. Med. Chem. 9, 253–259 (1974)

    CAS  Google Scholar 

  • Ben-Zvi, Z., Mechoulam, R., Burstein, S.: Identification through synthesis of an active Δ6- THC metabolite. J. Am. Chem. Soc. 92, 3468 (1970)

    PubMed  CAS  Google Scholar 

  • Bercht, C.A.L., Lousberg, R.J.J.C., Küppers, F.J.E.M., Salemink, C.A.: Cannabicitran: A new naturally occurring tetracyclic diether from Lebanese Cannabis sativa. Phytochemistry 13, 619–621 (1974)

    CAS  Google Scholar 

  • Bhargava, N.H.: Potential therapeutic applications of naturally occurring and synthetic cannabinoids. Gen. Pharmacol. 9, 195–213 (1978)

    PubMed  CAS  Google Scholar 

  • Braude, M.C., Szara, S. (eds.): The pharmacology of marihuana. New York: Raven 1976

    Google Scholar 

  • Burstein, S.H.: Labeling and metabolism of the THC’s. In: Marijuana. Chemistry, pharmacology, metabolism and clinical effects. Mechoulam, R. (ed.), pp. 167–190. New York, London: Academic Press 1973

    Google Scholar 

  • Burstein, S.H., Menezes, F., Williamson, E., Mechoulam, R.: Metabolism of Δ6-THC, an active marihuana constituent. Nature 225, 87–88 (1970)

    PubMed  CAS  Google Scholar 

  • Cais, M., Dani, S., Josephy, Y., Modiano, A., Gershon, H., Mechoulam, R.: Studies of cannabinoid metabolites - a free radical immunoassay. FEBS Lett. 55, 257–260 (1975)

    PubMed  CAS  Google Scholar 

  • Chan, W.R., Magnus, K.E., Watson, H.A.: The structure of cannabitriol. Experientia 32, 283 (1976)

    PubMed  CAS  Google Scholar 

  • Claussen, U., Spulak, F. v., Körte, F.: Cannabichromene, ein neuer Haschisch Inhaltstoff. Tetrahedron 22, 1477–1479 (1966)

    CAS  Google Scholar 

  • Cohen, S., Stillman, R.C. (eds.): The therapeutic potential of marihuana. New York: Plenum 1976

    Google Scholar 

  • Crombie, L., Ponsford, R., Shani, A., Yagnitinsky, B., Mechoulam, R.: Photochemical produc-tion of cannabicyclol from cannabichromene. Tetrahedron Letters 55, 5771–5772 (1968)

    PubMed  Google Scholar 

  • Crombie, W.M.L.: The analysis of cannabis. In: Cannabis and health. Graham, J.D.P. (ed.) pp. 21–41. London: Academic Press 1976

    Google Scholar 

  • Cunha, I.M., Carlini, E.A., Pereira, A.E., Ramos, O.L., Gagliardi, R., Sanvito, W.L., Lander, N., Mechoulam, R.: Chronic administration of cannabidiol to healthy volunteers and epileptic patients. Pharmacology 21, 175–185 (1980)

    PubMed  CAS  Google Scholar 

  • El-Feraly, F.S., Elsohly, M.A., Boeren, E.G., Turner, C.E., Ottersen, T., Aasen, A.: Crystal and molecular structure of cannabispiran and its correlation to dehydrocannabispiran. Tetrahedron 33, 2373–2387 (1977)

    CAS  Google Scholar 

  • Fairbairn, J.W.: The pharmacognosy of Cannabis. In: Cannabis and Health. Graham, J.D.P. (ed.), pp. 3–19. London: Academic 1976

    Google Scholar 

  • Fairbairn, J.W., Liebman, J.A.: The cannabinoid content of Cannabis sativa L. grown in England. J. Pharm. Pharmacol. 26, 413–419 (1974)

    PubMed  CAS  Google Scholar 

  • Fenimore, D.C., Freeman, R.R., Loy, P.R.: Determination of zl9-THC in blood by electron capture gas chromatography. Anal. Chem. 45, 2331–2335 (1973)

    CAS  Google Scholar 

  • Foltz, R., Fentiman, A.F., Leighty, E.G., Walter, J.L., Drewes, H.R., Schwartz, W.E., Page, T.F.Jr., Truitt, E.F.Jr.: Metabolite of ¿18-THC: Identification and synthesis. Science 168, 844–855 (1970)

    CAS  Google Scholar 

  • Forrest, I.S., Green, D.E., Rose, S.D., Skinner, G.C., Torres, D.M.: Fluorescentlabeled cannabinoids. Res. Commun. Chem. Pathol. Pharmacol. 2, 787–792 (1971)

    PubMed  CAS  Google Scholar 

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

    CAS  Google Scholar 

  • Gaoni, Y., Mechoulam, R.: The structure and synthesis of cannabigerol. Proc. Chem. Soc. 82, (1964b)

    Google Scholar 

  • Gaoni, Y., Mechoulam, R.: Cannabichromene, a new active principle in hashish. Chem. Commun. 20 (1966)

    Google Scholar 

  • Garrett, E.R., Hunt, C.A.: Picogram analysis of THC and application to biological fluids. J. Pharm. Sci. 62, 1211–1214 (1973)

    PubMed  CAS  Google Scholar 

  • Garrett, E.R., Hunt, C.A.: Physiochemical properties, solubility and protein binding of Δ 9- THC. J. Pharm. Sci. 63, 1056–1064 (1974)

    PubMed  CAS  Google Scholar 

  • Garrett, E.R., Hunt, C.A.: Separation and analysis of Δ 9-THC in biological fluids using HPLC and GLC. J. Pharm. Sci. 66, 20–26 (1977)

    PubMed  CAS  Google Scholar 

  • Garrett, E.R., Tsau, J.J.: Stability of THC’s. J. Pharm. Sci. 63, 1563–1574 (1974)

    PubMed  CAS  Google Scholar 

  • Gill, E.W., Jones, G.: Brain levels of Δ 1-THC and its metabolites in mice. Biochem. Pharmacol. 21, 2237–2248 (1972)

    PubMed  CAS  Google Scholar 

  • Gross, S.J., Soares, J.R.: Validated direct blood Δ 9-THC radioimmune quantitation. J. Anal. Toxicol. 2, 98–100 (1978)

    CAS  Google Scholar 

  • Grotte, H., Spiteller, G.: Neue Cannabinoide. J. Chromatogr. 154, 13–23 (1978)

    Google Scholar 

  • Hartley, J.P.R., Nogrady, S.G., Seaton, A., Graham, J.D.P.: Bronchodilator effect of Δ 1-THC. Br. J. Clin. Pharmacol. 5, 523–525 (1978)

    PubMed  CAS  Google Scholar 

  • Harvey, D.J., Martin, B.R., Paton, W.D.M.: Identification of metabolites of Δ1 and Δ6-THC containing a reduced double bond. J. Pharm. Pharmacol. 29, 495–497 (1977a)

    PubMed  CAS  Google Scholar 

  • Harvey, D.J., Martin, B.R., Paton, W.D.M.: Identification of di and tri-substituted hydroxy and ketone metabolites of Δ 1-THC in mouse liver. J. Pharm. Pharmacol. 29, 482–486 (1977b)

    PubMed  CAS  Google Scholar 

  • Herman, T.S., Jones, S.E., Dean, J., Leigh, S., Dorr, R., Moon, T.E., Salmon, S.E.: Nabilone, a potent antiemetic cannabinol with minimal euphoria. Biomedicine 27, 331–334 (1977)

    PubMed  CAS  Google Scholar 

  • Hivley, R.L., Mosher, W.A., Hoffmann, F.W.: Isolation of A6-THC from marijuana. J. Am. Chem. Soc. 88, 1832–1833 (1966)

    Google Scholar 

  • Hoellinger, H., Nam, N.H., Decauchereux, J.F., Pichat, L.: Synthese de Δ8 et Δ 9-THC deuteries et trities. J. Label. Compounds Radiopharm. 13, 401–415 (1977)

    CAS  Google Scholar 

  • Karniol, I.G., Carlini, E.A.: The content of A9-THC does not explain all biological activity of some Brazilian marihuana samples. J. Pharm. Pharmacol. 24, 833–835 (1972)

    PubMed  CAS  Google Scholar 

  • Knaus, E.E., Coutts, R.T., Kozakoff, C.W.: The separation, identification and quantitation of cannabinoids and their derivatives using HPLC. J. Chromatogr. Sci. 14, 525–530 (1976)

    PubMed  CAS  Google Scholar 

  • Körte, F., Haag, M., Claussen, U.: Tetrahydrocannabinol carboxylic acid, a component of hashish. Angew. Chem. [Engl.]. 4, 872 (1965)

    Google Scholar 

  • Lawrence, D.K., Gill, E.W.: The effects of Δ 1-THC and other cannabinoids on spin labeled liposomes and their relationship to mechanisms of general anesthesia. Mol. Pharmacol. 11, 595–602 (1975)

    PubMed  CAS  Google Scholar 

  • Leighty, E.G., Fentiman, A.F.Jr., Foltz, R.L.: Long-retained metabolites of Δ9 and Δ 8-THC identified as novel fatty acid conjugates. Res. Commun. Chem. Pathol. Pharmacol. 14, 13–28 (1976)

    CAS  Google Scholar 

  • Lemberger, L.: The pharmacokinetic of Δ 9-THC and its metabolites. In: Marihuana. Chemistry, biochemistry and cellular effects. Nahas, G.G. (ed.), pp. 169–178. Berlin, Heidelberg, New York: Springer 1976

    Google Scholar 

  • Lemberger, L., Rubin, A.: Physiologic disposition of drugs of abuse. New York: Spectrum 1976

    Google Scholar 

  • Levy, S., Yagen, B., Mechoulam, R.: Identification of a C-glucuronide of Δ6-THC in a mouse liver. Science 200, 1391–1392 (1978)

    PubMed  CAS  Google Scholar 

  • Lyle, M.A., Pallante, S., Head, K., Fenselau, C.: Synthesis and characterization of glucuronides of cannabinol, cannabidiol, Δ 9-THC and Δ 8-THC. Biomed. Mass. Spectrom 4, 190–196 (1977)

    PubMed  CAS  Google Scholar 

  • Martin, B., Agurell, S., Nordqvist, M., Lindgren, J.-E.: Dioxygenated metabolites of cannabidiol formed by rat liver. J. Pharm. Pharmacol. 28, 603–608 (1976)

    PubMed  CAS  Google Scholar 

  • Martin, B.R., Harvey, D.J., Paton, W.D.M.: Biotransformation of cannabidiol in mice. Identification of new acid metabolites. Drug. Metab. Dispos. 5, 259–267 (1977)

    PubMed  CAS  Google Scholar 

  • Martin, B.R., Carney, J.M., Balster, R.L., Harris, L.S.: Behavioral activity, distribution and metabolism of 3H-Δ 9-THC in monkey brain following an intraventricular injection. Fed. Proc. 37, 164 (1978)

    Google Scholar 

  • McCallum, N.K., Eastwood, M.E.: In vivo binding of Δ 1-THC and CBN to rat serum proteins. J. Pharm. Pharmacol. 30, 384–386 (1978)

    PubMed  CAS  Google Scholar 

  • McCallum, N.K., Gugelmann, A., Brenninkmeijer, C.A.M., Mechoulam, R.: Isotope effect studies in the dehydrogenation of Δ 1-THC in the rat. Experientia 33, 1012–1014 (1977)

    PubMed  CAS  Google Scholar 

  • McCallum, N.K., Cairns, E.R., Ferry, D.G., Wong, R.J.: A simple GLC method for routine Δ 1-THC analyses of blood and brain. J. Anal. Toxicol. 2, 89–92 (1978)

    CAS  Google Scholar 

  • Mechoulam, R. (ed.): Marijuana. Chemistry, pharmacology, metabolism and clinical effects. New York, London: Academic 1973

    Google Scholar 

  • Mechoulam, R., Carlini, E.A.: Toward drugs derived from Cannabis. Naturwissenschaften 65, 174–179 (1978)

    PubMed  CAS  Google Scholar 

  • Mechoulam, R., Gaoni, Y.: Recent advances in the chemistry of hashish. In: Fortschritte Chemisch Organischer Naturstoffe. Zechmeister, L. (ed.), Vol. 25, pp. 175–213. Wien: Springer 1967a

    Google Scholar 

  • Mechoulam, R., Gaoni, Y.: The absolute configuration of Δ 1-THC. Tetrahedron Letters 12, 1109–1111 (1967b)

    PubMed  CAS  Google Scholar 

  • Mechoulam, R., Shvo, Y.: The structure of cannabidiol. Tetrahedron 19, 2073–2078 (1963)

    CAS  Google Scholar 

  • Mechoulam, R., Ben-Zvi, Z., Gaoni, Y.: On the nature of the Beam test. Tetrahedron 24, 5615 - 5624 (1968)

    PubMed  CAS  Google Scholar 

  • Mechoulam, R., Ben-Zvi, Z., Yagnitinsky, B., Shani, A.: A new THC acid, Tetrahedron Letters 28, 2339–2341 (1969)

    Google Scholar 

  • Mechoulam, R., Braun, P., Gaoni, Y.: A stereospecific synthesis of Δ 1-THC and Δ 1(6)-THC. J. Am. Chem. Soc. 89, 4552–4554 (1967)

    PubMed  CAS  Google Scholar 

  • Mechoulam, R., Braun, P., Gaoni, Y.: Syntheses of Δ 1-THC and related cannabinoids. J. Am. Chem. Soc. 94, 6159–6165 (1972)

    PubMed  CAS  Google Scholar 

  • Mechoulam, R., McCallum, N.K., Burstein, S.: Recent advances in the chemistry and biochemistry of Cannabis. Chem. Rev. 76, 75–112 (1976)

    CAS  Google Scholar 

  • Mechoulam, R., Shani, A., Edery, H., Grunfeld, Y.: Chemical basis of hashish activity. Science 169, 611–612 (1970)

    PubMed  CAS  Google Scholar 

  • Nahas, G.G.: Marihuana - deceptive weed. New York: Raven 1972

    Google Scholar 

  • Nahas, G.G. (ed.): Marihuana. Chemistry, biochemistry and cellular effects. Berlin, Heidelberg, New York: Springer 1976

    Google Scholar 

  • Nakano, S., Gillespie, H.K., Hollister, L.E.: A model for evaluation of antianxiety drugs with the use of experimentally induced stress: comparison of nabilone with diazepam. Clin. Pharmacol. Ther. 23, 54–62 (1978)

    PubMed  CAS  Google Scholar 

  • Nilsson, I.M., Agurell, S., Nilsson, J.L.G., Ohlsson, A., Sandberg, F., Wahlqvist, M.: Δ 1-THC: Structure of a major metabolite. Science 168, 1228–1229 (1970)

    PubMed  CAS  Google Scholar 

  • Novotny, M., Lee, M.L.: Detection of marijuana smoke in the atmosphere of a room. Experi- entia 29, 1038–1039 (1973)

    CAS  Google Scholar 

  • Pallante, S., Lyle, M.A., Fenselau, C.: Synthesis and characterization of glucuronides of 5′-OH-Δ 9-THC and 11-OH-Δ 9-THC. Drug Met. Dispos. 6, 389–395 (1978)

    CAS  Google Scholar 

  • Pars, H.G., Razdan, R.K., Howes, J.F.: Potential therapeutic agents derived from the cannabinoid nucleus. Adv. Drug Res. 11, 97–189 (1977)

    PubMed  CAS  Google Scholar 

  • Paton, W.D.M.: Pharmacology of marijuana. Annu. Rev. Pharmacol. 15, 191–220 (1975)

    PubMed  CAS  Google Scholar 

  • Petrzilka, T., Haefliger, W., Sikemeier, C.: Synthese von Haschisch - Inhaltsstoffen. Helv. Chim. Acta 52, 1102–1134 (1969)

    CAS  Google Scholar 

  • Pitt, C.G., Hobbs, D.T., Schran, H., Twine, C.E.Jr., Williams, D.L.: The synthesis of deuterium, carbon-14 and carrier-free tritium labeled cannabinoids. J. Label. Compounds Radiopharm. 11, 551–575 (1975)

    CAS  Google Scholar 

  • Razdan, R.K.: Recent advances in the chemistry of cannabinoids. Prog. Org. Chem. 8, 78–101 (1973)

    CAS  Google Scholar 

  • Razdan, R.K., Dalzell, H.C., Handrick, G.R.: A simple one-step synthesis of Δ 1-THC from p- mentha-2,8-diene-1 -ol and olivetol. J. Am. Chem. Soc. 96, 5860–5865 (1974)

    PubMed  CAS  Google Scholar 

  • Razdan, R.K., Howes, J.F., Uliss, D.B., Dalzell, H.C., Handrick, G.R., Dewey, W.L.: 8ß-Hydroxymethyl-Δ 1-THC, a novel physiologically active analog of Δ 1-THC. Experientia 32, 416–417 (1976a)

    PubMed  CAS  Google Scholar 

  • Razdan, R.K., Terris, B.Z., Pars, H.G., Plotnikoff, N.P., Dodge, P.W., Dren, A.T., Kyncl, J., Somani, P.: Drugs derived from cannabinoids. 2. Basic esters of N- and carbocyclic analogs. J. Med. Chem. 19, 454–461 (1976b)

    PubMed  CAS  Google Scholar 

  • Rosenfeld, J.: The simultaneous determination of A9- THC and 1 l-hydroxy-zl9-THC in plasma. Anal. Lett. 10, 917–930 (1977)

    CAS  Google Scholar 

  • Rosenthal, D., Harvey, T.M., Bursey, J.T., Brine, D.R., Wall, M.E.: Comparison of GC-MS methods for the determination of Δ 9-THC in plasma. Biomed. Mass. Spectrom 5, 312–316 (1978)

    PubMed  CAS  Google Scholar 

  • Sallan, S.E., Zinberg, N.E., Frei, E.: Antiemetic effect of Δ 9-THC in patients receiving cancer chemotherapy. N. Engl. J. Med. 293, 795–797 (1975)

    PubMed  CAS  Google Scholar 

  • Schou, J., Steentoft, A., Worm, K., Andersen, J.M., Nielsen, E.: Highly sensitive method for gas chromatography of THC and CBN. Acta Pharmacol. Toxicol. (Kbh). 30, 480–482 (1971)

    CAS  Google Scholar 

  • Segelman, A.B., Segelman, F.P., Star, A.E., Wagner, H., Seligman, O.: Structure of two C- diglycosyl-flavones from Cannabis sativa. Phytochemistry 17, 824–826 (1978)

    CAS  Google Scholar 

  • Shani, A., Mechoulam, R.: Photochemical reactions of CBD. Tetrahedron 27, 601–606 (1971)

    CAS  Google Scholar 

  • Shani, A., Mechoulam, R.: Cannabielsoic acids. Isolation and synthesis by a novel oxidative cyclization. Tetrahedron 30, 2437–2446 (1974)

    CAS  Google Scholar 

  • Shoyama, Y., Hirano, H., Nishioka, I.: Synthesis of cannabigerorcinic-carboxyl-14C acid, can- nabigerovarinic-carboxyl-14C-acid and cannabichromevarinic-carboxyl-14C-acid. J. Label. Comp. Radiopharm. 14, 835–842 (1978)

    CAS  Google Scholar 

  • Smith, R.M., Vaughan, C.G.: High pressure liquid chromatography of Cannabis. J. Chromatogr. 129, 347–354 (1976)

    PubMed  CAS  Google Scholar 

  • Spronck, H.J., Salemink, C.A.: Isolation and synthesis of olivetol derivatives formed in the pyrolysis of CBD. Ree. Trav. Chim. Bays-Bas. 97, 187–190 (1978)

    Google Scholar 

  • Spulak, F. v., Claussen, U., Fehlhaber, H.W., Körte, F.: Cannabidiolcarbonsaure-tetra hydro- cannabitriol-ester, ein neuer Haschisch-Inhaltsstoff. Tetrahedron 24, 5379–5383 (1968)

    Google Scholar 

  • Staquet, M., Gantt, C., Machin, D.; Effect of a nitrogen analog of THC on cancer pain. Clin. Pharmacol. Ther. 23, 397–401 (1978)

    PubMed  CAS  Google Scholar 

  • Tamir, I., Mechoulam, R., Meyer, A.Y.: Cannabidiol and phenytoin, a structural comparison. J. Med. Chem. 23, 220–223 (1980)

    PubMed  CAS  Google Scholar 

  • Teale, J.D., Forman, E.J., King, L.J., Piall, E.M., Marks, V.J.: The development of a radio immunoassay for cannabinoids in blood and urine. J. Pharm. Pharmacol. 21, 465–472 (1975)

    Google Scholar 

  • Turner, C.E., Hsu, M.H., Knopp, J.E., Schiff, P.L., Slatkin, D.J.: Isolation of cannabisativine, an alkaloid from Cannabis sativa L. J. Pharm. Sci. 65, 1084–1085 (1976)

    PubMed  CAS  Google Scholar 

  • Valle, J.R., Viera, J.E.V., Aucelio, J.G., Valio, I.F.M.: Influence of photoperiodism on canna- binoid content of Cannabis sativa L. Bull. Narcotics 30 /1, 67–68 (1978)

    CAS  Google Scholar 

  • Vinson, J.A. (ed.): Cannabinoid analysis in physiological fluids. Washington, D.C.: American Chemical Society 1979

    Google Scholar 

  • Vinson, J.A., Patel, D.D., Patel, A.H.: Detection of THC in blood and serum using a fluores-cent derivative and TLC. Anal. Chem. 49, 163–165 (1977)

    PubMed  CAS  Google Scholar 

  • Wahlqvist, M., Nilsson, I.M., Sandberg, F., Agurell, S., Granstrand, B.: Binding of Δ 1-TRC to human plasma proteins. Biochem. Pharmacol. 19, 2579–2589 (1970)

    PubMed  CAS  Google Scholar 

  • Wall, M.E., Brine, D.R., Brine, G.A., Pitt, G.G., Freudenthal, R.I., Christensen, A.D.: Isolation, structure and biological activity of several metabolites of zl9-THC. J. Am. Chem. Soc. 92, 3466–3468 (1970)

    PubMed  CAS  Google Scholar 

  • Wall, M.E., Brine, D.R., Perez-Reyes, M.: Metabolism of cannabinoids in man. In: The pharmacology of marihuana. Braude, M.C., Szara, S. (eds.), pp. 93–113. New York: Raven 1976

    Google Scholar 

  • Waller, C.W., Johnson, J.J., Buelke, J., Turner, C.E.: Marihuana: An annotated bibliography. New York: MacMillan 1976

    Google Scholar 

  • Williams, P.L., Moffat, A.C., King, L.J.: Combined HPLC and radio immunoassay for the quantitation of Δ 9-THC and some of its metabolites in human plasma. J. Chromatogr. 155, 273–283 (1978)

    PubMed  CAS  Google Scholar 

  • Willette, R.E. (ed.): Cannabinoid assays in humans. Rockville: National Institute on Drug Abuse 1976

    Google Scholar 

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

    CAS  Google Scholar 

  • Yagen, B., Levy, S., Mechoulam, Ben-Zvi, Z.: Synthesis and enzymatic formation of a C-glucuronide of Δ6-THC. J. Am. Chem. Soc. 99, 6444–6446 (1977)

    CAS  Google Scholar 

  • Yisak, W., Agurell, S., Lindgren, J.-E., Widman, M.: In vivo metabolites of CBN identified as fatty acid conjugates. J. Pharm. Pharmacol. 30, 462–463 (1978)

    PubMed  CAS  Google Scholar 

Download references

Authors
  1. R. Mechoulam
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Institut für Pharmakologie, Bayer AG, Aprather Weg 18a, D-5600, Wuppertal 1, Germany

    F. Hoffmeister

  2. Institut für Arzneimittel des Bundesgesundheitsamtes, Stauffenbergstraße 13, D-1000, Berlin 30, Germany

    G. Stille

Rights and permissions

Reprints and permissions

Copyright information

© 1982 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Mechoulam, R. (1982). Chemistry of Cannabis. In: Hoffmeister, F., Stille, G. (eds) Psychotropic Agents. Handbook of Experimental Pharmacology, vol 55 / 3. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-67770-0_7

Download citation

  • DOI: https://doi.org/10.1007/978-3-642-67770-0_7

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-67772-4

  • Online ISBN: 978-3-642-67770-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation