title: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L.
abstract: The volatile constituents of drug samples derived from Cannabis sativa L. were investigated by means of headspace solid phase microextraction (HS-SPME) and gas chromatography techniques (GC-MS, GC×GC-MS). Samples of cannabis herb and hashish showed clear differences in their volatile chemical profiles, mostly resulting from photo-oxidation processes occurring during the transformation of fresh cannabis herb into hashish. Most unexpectedly, we could demonstrate hashish samples as containing remarkable amounts of a rare and unusual monoterpene - 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane - among the volatile compounds detected in their headspaces. We gave evidence for the formation of this compound from the light induced rearrangement of β-myrcene during the manufacture of hashish. In view of its high abundance among volatile constituents of cannabis resin and its scarce occurrence in other natural volatile extracts, we propose to rename this specific monoterpene hashishene.
authors.affiliation: Institut de Chimie de Nice, Université Nice-Sophia Antipolis (UNS), UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Marie
authors.initials: M
authors.lastname: Marchini
authors.affiliation: Institut National de Police Scientifique (INPS), 31 Avenue Franklin Roosevelt, 69134 Ecully Cedex, France.
authors.forename: Céline
authors.initials: C
authors.lastname: Charvoz
authors.affiliation: Institut National de Police Scientifique (INPS), 31 Avenue Franklin Roosevelt, 69134 Ecully Cedex, France.
authors.forename: Laurence
authors.initials: L
authors.lastname: Dujourdy
authors.affiliation: Institut de Chimie de Nice, Université Nice-Sophia Antipolis (UNS), UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Baldovini
authors.affiliation: Institut de Chimie de Nice, Université Nice-Sophia Antipolis (UNS), UMR 7272 CNRS, Parc Valrose, 06108 Nice Cedex 2, France. Electronic address: jfilippi@unice.fr.
authors.forename: Jean-Jacques
authors.initials: JJ
authors.lastname: Filippi
mesh_terms: D000080462:Acyclic Monoterpenes; D002188:Cannabis / Q000737:chemistry*; D003512:Cyclohexanones / Q000032:analysis*; D008401:Gas Chromatography-Mass Spectrometry / Q000379:methods*; D039821:Monoterpenes / Q000737:chemistry; D010084:Oxidation-Reduction; D055668:Photochemical Processes; D012116:Resins, Plant / Q000737:chemistry; D052617:Solid Phase Microextraction / Q000379:methods; D013237:Stereoisomerism
chemical_list: C000599752:5,5-dimethyl-1-vinylbicyclo(2.1.1)hexane; D000080462:Acyclic Monoterpenes; D003512:Cyclohexanones; D039821:Monoterpenes; D012116:Resins, Plant; C008574:beta-myrcene
keywords: Cannabis sativa L.; Hashish; Myrcene rearrangement; Photo-oxidation processes; Volatile marker