Constituents of Cannabis sativa L. I. Propyl homologs of cannabinoids from an Indian variant.
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Biomedical subjects
Publications and source records attributed to C E Turner.
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Cannabichromene (CBC) is one of four major cannabinoids in Cannabis sativa L. and is the second most abundant cannabinoid in drug-type cannabis. Cannabichromene and some of its homologs, analogs, and isomers were evaluated for antiinflammatory, antibacterial, and antifungal activity. Antiinflammatory activity was evaluated by the carrageenan-induced rat paw edema and the erythrocyte membrane stabilization method. In both tests, CBC was superior to phenylbutazone. Antibacterial activity of CBC and its isomers and homologs was evaluated using gram-positive, gram-negative, and acid-fast bacteria. Antifungal activity was evaluated using yeast-like and filamentous fungi and a dermatophyte. Antibacterial activity was strong, and the antifungal activity was mild to moderate.
A gas-chromatographic procedure is outlined for the analysis of cocaine and cis- and trans-cinnamoylcocaines in coca leaves. The procedure was applied to the determination of these alkaloids in coca leaves collected from three different locations in Peru. The extraction of alkaloids from plant material was accomplished following the procedure we previously outlined. Recovery of cinnamoylcocaines was quantitative and the average coefficient of variation was 6.8%. Using androst-4-ene-3,17-dione as the internal standard, the correlation coefficient (r2) as determined from the calibration curve of trans-cinnamoylcocaine was 0.99 and the response factor 0.72. Observable differences in relative proportions of cis and trans isomers of cinnamoylcocaine were found among samples from different locations. In addition, the relative proportions of the total cinnamoylcocaine concentration to cocaine varied with sample origin. We have also examined coca extracts using a nitrogen detector and by gas chromatography--mass spectrometry. The nature and identity of other nitrogenous peaks in the chromatograms are also discussed.
The relationship between route of cocaine administration, that is, free base/crack smoking (FB), intravenous injection (IV), and nasal insufflation (NS) and level of violence was studied. The authors hypothesized that the route that produced the most intense effects (i.e., FB > IV > NS) would produce the highest level of violence. Over a 12-month period, 194 cocaine users were screened. After excluding polydrug users, 101 patients of both sexes participated in this study for the evaluation of expressions of violence. Evaluations were conducted by a structured questionnaire. The order of level of increased violence matched that of the most "intense" route of administration for some measures only. FB and IV use generally produced the same level of violence for most measurements. Both FB and IV routes produced more violence than NS. Violent actions requiring sustained activity (e.g., rape, burglary, and armed robbery) showed no relationship to route. The difference in levels in violence between males and females varied according to circumstance, not route of administration.
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Two new dihydrostilbene compounds (named cannabistilbenes I and II) were isolated from a polar acidic fraction of a Panamanian variant of Cannabis sativa grown in Mississippi. The structure of cannabistilbene I was shown to be 3,4'-dihydroxy-5-methoxy-3'-(3-methylbut-2-enyl)-dihydrostilben e (1) from spectral data which was confirmed by synthesis. There is spectral evidence to indicate that cannabistilbene II could be represented by either structure 3 or 4.
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A spectrophotometric method used to test for paraquat in 160 confiscated marijuana samples is described. Twenty of these samples (12.5 per cent) tested positive for paraquat. Nine confiscated hash oil samples tested negative. The identification of paraquat was proven by isolation, chromatography, and spectral methods. The cannabinoids in paraquat positive Cannabis samples were analysed.
A method for the determination of cocaine content in coca leaves (Erythroxylum coca) has been developed. The procedure involves refluxing the powdered leaves in 95% ethanol for 15 minutes, followed by acid-base partitioning with chloroform and a GLC assay. The recovery of cocaine was quantitative. This procedure was applied to determine cocaine content in three samples of Erythroxylum coca Lam. collected from different geographic locations in Peru. Using androst-4-ene-3,17-dione as the internal standard the calibration curve was linear over a factor of 0.5 to 10 fold cocaine concentration relative to internal standard. The slope (b) was 0.733, the coefficient of determination (r2) was 1.00 and the average precision was 3.9%.
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Three spiro-compounds, namely cannabispiran, dehydrocannabispiran and beta-cannabispiranol, and 2 dihydrostilbenes [3-(2-(3-hydroxy-4-methoxyphenyl)ethyl)-5-methoxyphenol and canniprene] were isolated from a polar fraction of a Panamanian variant of Cannabis sativa L. grown in Mississippi, United States of America. The plant material was extracted with 95% ethanol and the dried ethanol extract was then partitioned between chloroform and water. The chloroform fraction was fractionated between hexane and 3N sodium hydroxide solution. Acidification of the basic fraction followed by extraction with ether afforded a polar acidic fraction from which the above-mentioned compounds were isolated through repeated chromatography. The structures of the above compounds were determined by spectral means as well as by comparison with reference samples. The isolation of two dihydrostilbenes and three spiro-indan compounds from a single variant provides good support that the dihydrostilbenes are the natural precursors to the spiro-indan compounds.
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