Constituents of Cannabis sativa L. XVIII--Electron voltage selected ion monitoring study of cannabinoids.

Cannabis sativa L. contains more than 420 different constituents. Sixty-one of these constituents are cannabinoids. The electron voltage selected ion monitoring technique was used in the study of this unique group on natural compounds. Mass spectra of each compound were recorded at various eV settings (5.5-21 eV). The electron voltage selected ion recordings were obtained by plotting the relative intensities of characteristic fragment ions against electron voltage. The method was proven useful in the structure analysis of cannabinoids since it requires only minute quantities of sample. It was possible to recognize homologs and to differentiate positional and double bond isomers as well as cannabinoids with the same molecular weight.

New GLC analysis of urushiol congeners in different plant parts of poison ivy, Toxicodendron radicans.

Methods are presented for the direct GLC analysis of the catechol C15 alkenyl side-chain congeners contained in the urushiol fraction of poison ivy (Toxicodendron radicans) and the C17 homologs of poison oak (Toxicodendron diversilobum). A number of liquid phases were investigated and demonstrated varying degrees of separation. The methods developed were applied to the analysis of the urushiol fractions obtained from different plant parts of poison ivy. The effects of extraction before and after drying demonstrated tht a larger percentage of urushiol was obtained when the fresh plant material was extracted with ethanol.

Characterization and mass spectral analysis of some grayanotoxin derivatives.

The mass spectra of grayanotoxin III and some of its mono-, di, and tri-ester derivatives are discussed. Some of the physiological responses of this compound class are also presented. The extraction of this material from a natural source is discussed as well as the schemes for ester derivatization and spectral characterization of all compounds studied. High resolution mass spectral analysis and comparison of the mass spectra of similar compounds were used to define possible fragmentation mechanisms.

Characterization of poison oak urushiol.

Procedures are described that were used in the isolation and characterization of urushiol components reported to be the allergenic constituents of poison oak, Toxicodendron diversilobum. Characterization of these components by spectral techniques indicated they are unsaturated congeners of 3-heptadecylcatechol, possessing one, two, or three double bonds in an unbranched C17 side chain. These components are shown to differ from those isolated from poison ivy, Toxicodendron radicans, by a - CH2CH2-unit in the unbranched alkyl side chain.

Identification of phosphorodiamidic acid mustard as a human metabolite of cyclop hosphamide.

An active metabolite of cyclophosphamide, N,N-bis(2-chloroethyl)phosphorodiamidic acid, has been confirmed as a circulating and excreted metabolite in patients receiving the drug in therapy, by selected ion monitoring on a gas chromatograph mass spectrometer.

Constituents of Cannabis sativa L. VIII: Possible biological application of a new method to separate cannabidiol and cannabichromene.

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.