title: Thermal isomerization of cannabinoid analogues.
abstract: Thermal isomerization of CBC(an) to THC(an) [nonaromatic analogues of plant cannabinoids cannabichromene (CBC) and Delta(1)-tetrahydrocannabinol (THC), respectively] is predicted in silico and demonstrated experimentally. Density functional theory calculations support a similar isomerization mechanism for the corresponding plant cannabinoids. Docking studies suggest that THC(an), although nonaromatic, has a CB(1) receptor binding affinity similar to that of natural THC.
authors.affiliation: Department of Chemistry, University of California, Riverside, California 92521, USA.
authors.forename: Angie
authors.initials: A
authors.lastname: Garcia
authors.forename: Dan
authors.initials: D
authors.lastname: Borchardt
authors.forename: Chia-En A
authors.initials: CE
authors.lastname: Chang
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Marsella
mesh_terms: D002186:Cannabinoids / Q000737:chemistry*; D013759:Dronabinol / Q000737:chemistry*; D006358:Hot Temperature; D007536:Isomerism
chemical_list: D002186:Cannabinoids; D013759:Dronabinol; C010695:cannabichromene