title: Metabolic Fate of Hallucinogenic NBOMes.
abstract: 2,5-Dimethoxy-N-benzylphenethylamines (NBOMes) are very potent 5-HT2AR agonists. Illicit use of these psychedelic compounds has emerged in recent years, and several fatalities have been linked to their recreational use. In its [(11)C]-labeled form, one NBOMe (25B-NBOMe) was recently developed as a PET-ligand for clinical investigations of 5HT2AR ([(11)C]Cimbi-36). Herein, we have identified the phase I and phase II metabolites of 25B-NBOMe in pigs as well as in humans. We find that the primary route of metabolism is 5'-demethylation, followed by conjugation to glucuronic acid. Carbon-11 labeling of 25B-NBOMe in three different positions followed by in vivo evaluation in pigs and humans corroborated these findings.
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Sebastian
authors.initials: S
authors.lastname: Leth-Petersen
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Charlotte
authors.initials: C
authors.lastname: Gabel-Jensen
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Nic
authors.initials: N
authors.lastname: Gillings
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Szabolzs
authors.initials: S
authors.lastname: Lehel
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Hanne D
authors.initials: HD
authors.lastname: Hansen
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Gitte M
authors.initials: GM
authors.lastname: Knudsen
authors.affiliation: Department of Drug Design and Pharmacology and ‡Department of Pharmacy, University of Copenhagen , DK-2100 Copenhagen, Denmark.|PET and Cyclotron Unit and ∥Neurobiology Research Unit and Center for Integrated Molecular Brain Imaging, Copenhagen University Hospital , DK-2100 Copenhagen, Denmark.
authors.forename: Jesper L
authors.initials: JL
authors.lastname: Kristensen
mesh_terms: D000818:Animals; D006213:Hallucinogens / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D008862:Microsomes, Liver / Q000737:chemistry / Q000378:metabolism; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry / Q000378:metabolism*; D049268:Positron-Emission Tomography; D013552:Swine / Q000378:metabolism*
chemical_list: C000612304:2,5-dimethoxy-N-benzylphenethylamine; D006213:Hallucinogens; D010627:Phenethylamines