Introduction: The plant Cannabis sativa L. has a long history for human being since about BC 2000 for its use as fiber material, food and folk medicine; cannabis (hemp, marijuana) means the whole plant itself and its dried products except for its stem and seeds. The word “hashish” is mainly used for the resin of the cannabis plant. Since the main component of cannabis, ∆9-tetrahydrocannabinol (∆9-THC), has various psychopharmacological effects including hallucination, the cannabis and its components are being controlled under the Cannabis Control Law and the Narcotics Control Law in Japan. For such legal control, analysis of cannabis components. | Cannabinoids and their metabolites by Kazuhito Watanabe Introduction The plant Cannabis sativa L. has a long history for human being since about BC 2000 for its use as fiber material food and folk medicine cannabis hemp marijuana means the whole plant itself and its dried products except for its stem and seeds. The word hashish is mainly used for the resin of the cannabis plant. Since the main component of cannabis A9-tetrahydrocannabi-nol A9-THC has various psychopharmacological effects including hallucination the cannabis and its components are being controlled under the Cannabis Control Law and the Narcotics Control Law in Japan. For such legal control analysis of cannabis components and their metabolites is required for plant specimens and human specimens. The cannabis contains more than 60 analogous components with a C21 skeleton they are comprehensively called cannabinoids . The main cannabinoids are A9-THC cannabidiol CBD and cannabinol CBN . The major metabolic pathway of A9-THC is shown in Fig. the methyl group in the 11-position is oxidized to produce A9-THC-11-oic acid to be excreted into urine 1 2 . To diagnose the abuse of cannabis or its component the analysis of A9-THC-11-oic acid in urine is essential. In this chapter a GC method for analysis of cannabis components in plant specimens and a GC MS method for A9-THC-11-oic acid in urine are presented. O Figure nCH3 A9-THC CHzOH 11-hydroxy-A 9-THC 11-oxo-A9-THC COOH A9-THC-ll-oic acid Major metabolic pathway of A9-THC. Springer-Verlag Berlin Heidelberg 2005 188 Cannabinoids and their metabolites GC analysis of cannabinoids in plant specimens3 Reagents and their preparation Extraction and purification of cannabinoids 3 Cannabis sativa L. is being grown at Hokuriku University Faculty of Pharmaceutical Sciences with permission from the Government. The dried plant is minced and immersed in 20 volumes of methanol for 2 days for extraction this procedure is repeated once. The combined .