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Four different cannabinoids were converted to their 1-dimethyl-aminonaphthalene-5-sulfonate (dansyl) derivatives. Standards mixtures were separated by high pressure liquid chromatography and detected with an experimental filter fluorometer with sub-nanogram sensitivity. The effect of solvent properties on fluorescence spectra and quantum yields was also studied.

A radioimmunoassay (R.I.A.), using a sheep antiserum and 3-H-T.H.C., has been developed for the measurement of tetrahydrocannabinol (T.H.C.) in plasma and urine. The antiserum cross-reacts with T.H.C. metabolites, but nevertheless possesses sufficient group specificity and sensitivity to permit measurement of cannabinoids in plasma and urine of animals and volunteers following the administration of pure T.H.C. Subjective effects experienced by the volunteers seemed to correlate with plasma-T.H.C. levels. The examination of random plasma urine samples collected from patients attending a drug-addiction clinic revealed the presence of measurable amounts of cannabinoids in several of them.

Delta9-and-delta8-Tetrahydrocannabinol, delta9-tetrahydrocannabinolic acid, cannabidiol, cannabidolic acid, cannabinol, cannabinolic acid, cannabichromene and cannabichromenic acid were located in the liquid chromatogram of cannabis. Identifications were confirmed by gas chromatography-mass spectrometry.

The crystal and molecular structure of the title compound C-22H-30O-4, has been determined by X-ray methods using 1106 reflections above background level collected by counter methods. The crystals are orthorhombic, space group P2-12-12-1 with cell dimensions a equals 16.514(2) A; b equals 14.324(2) A; c equals 8.744(1) A; there are four molecules per unit cell. The structure was refined to an R of 0.084 (weighted R-w equals 0.068). The cyclohexene and the pyran part of the molecule occurs in the half-chair conformation. The bond distances and angles, and a slight twist of the benzene ring, indicate considerable stains in the aromatic system. Both the phenolic and carboxylic group are significantly out of the plane through the aromatig ring. The angle between this plane and a plane through the cyclohexene ring is 37.7 degrees. The pentyl sidechain occurs in an extended gauche conformation, and the thermal parameters of this part of the molecule are very high. The molecules are held together by van der Waals forces in the c-directions, and hydrogen bonds (2.688 A) from phenolic to carboxylic groups in the a-b plane. There is a short ultra-molecular hydrogen bond (2.490 A) from the carboxylic group to the pyran oxygen.

The in vivo transformations of cannabinol (CBN) in the mouse have been studied and a pattern of metabolism established. As with other cannabinoids, the 7 position and the side chain are hydroxylated followed by further oxidation to acidic metabolites. Two of these CBN metabolites have been isolated previously as metabolites of delta1-tetrahydrocannabinol (THC) suggesting that CBN may be a transformation product of delta1-THC.

Chronic cannabis intoxication of a significant fraction of the male population still prevails in Morocco. The preparation used (kif) is a powder made from the dried flower of the female plant. It contains 2 to 3% THC and is smoked mixed with tobacco (1/3 of the mixture). Cultivation of kif is tolerated in an area of 60 square miles in the high Rif mountain of Northern Morocco, where it constitutes the main cash crop of the local farmers. A significant percentage (50%?) of the men in the area also consume kif regularly. This cultivation is spreading to neighboring areas. Moroccan health authorities claim that cannabis intoxication represents a major health hazard. There exist little data correlating chronic usage of kif with pathological states in these areas of large production and consumption. This dearth of information due to lack of local medical personnel could be alleviated by a combined medical and ethnological study.

The on-column flash methylation of synthetic cannabidiol, cannabichromene, and cannabivarin by trimethylanillinium hydroxide offers a rapid, simple GLC method for their distinction. The phenolic groups of other cannabinoids are methylated by the procedure described.

Synthetic and naturally occurring cannabidiol and cannabichromene were distinctly separated without derivation by GLC using a 6% OV-1 column; an artifact of cannabichromene, cannabicyclol, was separated from (minus)-delta9-trans-tetrahydrocanna-bivarin. This procedure is versatile and applicable for the quantitation of Cannabis containing both cannabidiol and cannabichromene. Biological interaction among (minus)-delta9-trans-tetrhydrocanabinol, cannabichromene, and other cannabinoids in natural Cannabis preparations can now be studied. In the phenyl methyl silicone polymer series, cannabidiol precedes ca-nabichromene on columns containing below a 50% phenyl-to-methyl ratio. Columns containing below a 50% phenyl-to-methyl ratio. Columns containing a 50:50 or greater ratio of phenyl to methyl reverse the separation order with cannabichromene preceding cannabidiol.

This clinical brief is a survey of procedures, components and kits presently available for detecting and quantitating drugs of abuse in biologic fluids by radioimmunoassay (RIA).

The objective of this study was the production of smoke condensate from the marijuana cigarettes on schedule for the bioassay study and involved quality control on each batch of smoke condensate. Examination of the condensate production data (tables 1 and 2) reveal that it is not possible to strictly control the butt length of cigarettes when smoked on a robot smoking machine thereby accounting for some variation in the yield of the dry particulate matter and increment9-tetrahydrocannabinol. No increment8-tetrahydrocannabinol was detected in any batch of the smoke condensate. Recently, Hoffman and co-workers (13) have reported that marijuana that exhibited carcinogenic potential similar to tobacco cigarette smoke condensate in the dermal assay in mice.

The controversy concerning the taxonomic status of the genus Cannabis has now advanced to a stage where the forensic scientist has limitations to his testimony in identification of "marihuana" plant material in jurisdictions where the law defines "marihuana" as Cannabis sativa L. Whether the genus Cannabis is monotypic or polytypic is as yet uncertain, but recent taxonomic reviews weigh heavily toward the existence of three or more species within the genus. The taxonomists or forensic scientists cannot, therefore, positively state for fact that C. sativa is the only species existing within the genus Cannabis. The popular concept of "marihuana" is actually based on the chemical characteristics of the plant Cannabis, rather than on the taxonomic classification. This is evident in its inclusion as a drug or hallucinogenic substance under Federal and local statutes. It is therefore proposed that "marihuana" be redefined legally to include all members belonging to the genus, in jurisdictions where legal definition warrants such an act, or that these jurisdictions follow the format set forth by Federal rulings.

Plasma chromatography as a method for ultratrace qualitative and quantitative detection of organic compounds is especially well suited for detection of gas chromatographic effluents. The optimum range of sample quantity is 10-6 to 10-12 g for detection and identification of a compound by use of its characteristic positive and negative mobility spectra. The type of reference mobility spectra produced by alkanes, aromatics, esters, halogenated compounds, nitrogenated compounds and organic acids have been previously reported. This study presents the reference mobility spectra produced for lysergic acid diethylamide (LSD), delta-9-tetrahydrocannabinol (delta-9-THC), digitoxigenin and several biochemical compounds of research significance. LSD and delat-9-THC in a mixture can be detected and identified by plasma chromatography positive mobility spectra in quantities of 10-7 g or less. All the compounds investigated in this study display strong MH-+ ions along with other ions primarily of the type (M)NO-+, (M)2H-+. None of these compounds exhibits negative mobility spectra.

Antibodies, for use in radioimmunoassay, have been raised in sheep by immunization with a conjugate of delta9-tetrahydrocannabinol hemisuccinate and bovine serum albumin. Antiserum titre and avidity were increased by successive booster doses of conjugate. The high degree of non-specific binding encountered in the radioimmunoassay of cannabinoids was reduced by the use of the solubilizing detergent Triton X-405 and by restricting protein concentration in the assay medium. Plasma samples were deproteinized with ethanol before assay, but urine was directly assayed. High avidity antibodies and high specific activity [3H]-delta9-tetrahydrocannabinol permitted the detection of 50 pg of cross-reacting cannabinoids--a sensitivity of 7-5 ng ml-1 of plasma and 1-0 ng ml-1 of urine. Whilst apparently specific for the three-ringed cannabinoid nucleus, the assay antiserum cross-reacted with several cannabinoids, both natural compounds and metabolites. Partial identification of cross-reacting cannabinoids was achieved by the use of pure compounds and by the assay of plasma and urine samples collected from rabbits given pure cannabinoids intravenously.