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  1. Article ; Online: Enantioselective Total Synthesis of (-)-Δ

    Ametovski, Adam / Lupton, David W

    Organic letters

    2019  Volume 21, Issue 4, Page(s) 1212–1215

    Abstract: Enantioselective syntheses of (-)- ... ...

    Abstract Enantioselective syntheses of (-)-Δ
    Language English
    Publishing date 2019-02-06
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.9b00198
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  2. Article: Enantioselective Total Synthesis of (−)-Δ9-Tetrahydrocannabinol via N-Heterocyclic Carbene Catalysis

    Ametovski, Adam / David W. Lupton

    Organic letters. 2019 Feb. 06, v. 21, no. 4

    2019  

    Abstract: Enantioselective syntheses of (−)-Δ8-tetrahydrocannabinol ((−)-Δ8-THC) and (−)-Δ9-THC have been achieved in eight and 10 steps, respectively, from a known cinnamic acid. The syntheses take advantage of an enantioselective N-heterocyclic carbene (NHC)- ... ...

    Abstract Enantioselective syntheses of (−)-Δ8-tetrahydrocannabinol ((−)-Δ8-THC) and (−)-Δ9-THC have been achieved in eight and 10 steps, respectively, from a known cinnamic acid. The syntheses take advantage of an enantioselective N-heterocyclic carbene (NHC)-catalyzed (4 + 2) annulation between donor–acceptor cyclobutanes and cinnamoyl fluorides to construct the highly enantioenriched cycloxyl β-lactone shown. Having constructed this A-ring precursor, elaboration to (−)-Δ8-THC is achieved through β-lactone alcoholysis followed by oxidation, dual decarboxylation, trimethylation, and cationic cyclization. Finally, the conversion to (−)-Δ9-THC is achieved with established chemistry.
    Keywords alcoholysis ; carbenes ; catalytic activity ; chemical structure ; cinnamic acid ; decarboxylation ; enantioselectivity ; heterocyclic nitrogen compounds ; organofluorine compounds ; oxidation
    Language English
    Dates of publication 2019-0206
    Size p. 1212-1215.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1523-7052
    DOI 10.1021/acs.orglett.9b00198
    Database NAL-Catalogue (AGRICOLA)

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  3. Article ; Online: Synthesis and Functional Evaluation of Synthetic Cannabinoid Receptor Agonists Related to ADB-HEXINACA.

    Sparkes, Eric / Timmerman, Axelle / Markham, Jack W / Boyd, Rochelle / Gordon, Rebecca / Walker, Katelyn A / Kevin, Richard C / Hibbs, David E / Banister, Samuel D / Cairns, Elizabeth A / Stove, Christophe / Ametovski, Adam

    ACS chemical neuroscience

    2024  Volume 15, Issue 9, Page(s) 1787–1812

    Abstract: ADB-HEXINACA has been recently reported as a synthetic cannabinoid receptor agonist (SCRA), one of the largest classes of new psychoactive substances (NPSs). This compound marks the entry of ... ...

    Abstract ADB-HEXINACA has been recently reported as a synthetic cannabinoid receptor agonist (SCRA), one of the largest classes of new psychoactive substances (NPSs). This compound marks the entry of the
    MeSH term(s) Cannabinoid Receptor Agonists/pharmacology ; Cannabinoid Receptor Agonists/chemical synthesis ; Humans ; Receptor, Cannabinoid, CB1/agonists ; Receptor, Cannabinoid, CB1/metabolism ; Receptor, Cannabinoid, CB2/agonists ; Receptor, Cannabinoid, CB2/metabolism ; HEK293 Cells ; Structure-Activity Relationship ; Animals
    Chemical Substances Cannabinoid Receptor Agonists ; Receptor, Cannabinoid, CB1 ; Receptor, Cannabinoid, CB2
    Language English
    Publishing date 2024-04-10
    Publishing country United States
    Document type Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.3c00818
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: In vitro evaluation of the interaction of the cannabis constituents cannabichromene and cannabichromenic acid with ABCG2 and ABCB1 transporters.

    Etchart, Maia G / Anderson, Lyndsey L / Ametovski, Adam / Jones, Peter M / George, Anthony M / Banister, Samuel D / Arnold, Jonathon C

    European journal of pharmacology

    2022  Volume 922, Page(s) 174836

    Abstract: Cannabichromene (CBC) and cannabichromenic acid (CBCA) are cannabis constituents currently under evaluation for their therapeutic potential, but their pharmacological properties have not been thoroughly investigated. The most studied ATP-binding cassette ...

    Abstract Cannabichromene (CBC) and cannabichromenic acid (CBCA) are cannabis constituents currently under evaluation for their therapeutic potential, but their pharmacological properties have not been thoroughly investigated. The most studied ATP-binding cassette (ABC) transporters, ABC subfamily G member 2 (ABCG2) and ABC subfamily B member 1 (ABCB1) limit absorption of substrate drugs in the gut and brain. Moreover, inhibitors of these proteins can lead to clinically significant drug-drug interactions (DDIs). The current study sought to examine whether CBC and CBCA affect ABCB1 and ABCG2 to advance their basic pharmacological characterisation. The plant cannabinoids CBC and CBCA were screened in vitro in a bidirectional transport assay to determine whether they were substrates and/or inhibitors of ABCB1 and ABCG2. Transwell assays with polarized epithelial Madin-Darby Canine Kidney II (MDCK) cells expressing ABCB1 or ABCG2 were used. Samples were measured using liquid chromatography tandem mass spectrometry (LC-MS/MS). CBCA was found to be an ABCB1 substrate, but not an ABCG2 substrate. CBC was not a substrate of either transporter. Neither CBCA nor CBC inhibited ABCB1 transport of prazosin or ABCG2 transport of digoxin. In silico molecular docking suggested CBCA binds ABCB1 in the access tunnel and the central binding pocket. CBC, an agent with anticonvulsant, anti-inflammatory and anti-depressant properties, is not a substrate or inhibitor of ABCB1 or ABCG2, which is favourable to its therapeutic development. CBCA is an ABCB1 substrate in vitro which might contribute to its poor absorption. These findings provide important basic pharmacological data to assist the therapeutic development of these cannabis constituents.
    MeSH term(s) ATP-Binding Cassette Transporters/metabolism ; Animals ; Cannabinoids/pharmacology ; Cannabis/metabolism ; Chromatography, Liquid ; Dogs ; Molecular Docking Simulation ; Tandem Mass Spectrometry
    Chemical Substances ATP-Binding Cassette Transporters ; Cannabinoids ; cannabichromene (K4497H250W)
    Language English
    Publishing date 2022-03-16
    Publishing country Netherlands
    Document type Journal Article
    ZDB-ID 80121-5
    ISSN 1879-0712 ; 0014-2999
    ISSN (online) 1879-0712
    ISSN 0014-2999
    DOI 10.1016/j.ejphar.2022.174836
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 522: Show issues Location:
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    Jg. 1995 - 2021: Lesesall (1.OG)
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  5. Article ; Online: Cannabichromene, Related Phytocannabinoids, and 5-Fluoro-cannabichromene Have Anticonvulsant Properties in a Mouse Model of Dravet Syndrome.

    Anderson, Lyndsey L / Ametovski, Adam / Lin Luo, Jia / Everett-Morgan, Declan / McGregor, Iain S / Banister, Samuel D / Arnold, Jonathon C

    ACS chemical neuroscience

    2021  Volume 12, Issue 2, Page(s) 330–339

    Abstract: Cannabis-based products are increasingly being used to treat refractory childhood epilepsies such as Dravet syndrome. Cannabis contains at least 140 terpenophenolic compounds known as phytocannabinoids. These include the known anticonvulsant compound ... ...

    Abstract Cannabis-based products are increasingly being used to treat refractory childhood epilepsies such as Dravet syndrome. Cannabis contains at least 140 terpenophenolic compounds known as phytocannabinoids. These include the known anticonvulsant compound cannabidiol (CBD) and several molecules showing emergent anticonvulsant properties in animal models. Cannabichromene (CBC) is a phytocannabinoid frequently detected in artisanal cannabis oils used in the community by childhood epilepsy patients. Here we examined the brain and plasma pharmacokinetic profiles of CBC, cannabichromenic acid (CBCA), cannabichromevarin (CBCV), and cannabichromevarinic acid (CBCVA) following intraperitoneal administration in mice. The anticonvulsant potential of each was then tested against hyperthermia-induced seizures in the
    MeSH term(s) Animals ; Anticonvulsants/pharmacology ; Anticonvulsants/therapeutic use ; Cannabinoids ; Child ; Epilepsies, Myoclonic/drug therapy ; Humans ; Mice ; NAV1.1 Voltage-Gated Sodium Channel ; Spasms, Infantile/drug therapy
    Chemical Substances Anticonvulsants ; Cannabinoids ; NAV1.1 Voltage-Gated Sodium Channel ; Scn1a protein, mouse ; cannabichromene (K4497H250W)
    Language English
    Publishing date 2021-01-04
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.0c00677
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Systematic evaluation of a panel of 30 synthetic cannabinoid receptor agonists structurally related to MMB-4en-PICA, MDMB-4en-PINACA, ADB-4en-PINACA, and MMB-4CN-BUTINACA using a combination of binding and different CB

    Grafinger, Katharina Elisabeth / Cannaert, Annelies / Ametovski, Adam / Sparkes, Eric / Cairns, Elizabeth / Banister, Samuel D / Auwärter, Volker / Stove, Christophe P

    Drug testing and analysis

    2021  Volume 13, Issue 7, Page(s) 1402–1411

    Abstract: Synthetic cannabinoid receptor agonists (SCRAs) are the second largest class of new psychoactive substances (NPS) and are associated with serious adverse effects and even death. Despite this, little pharmacological data are available for many of the most ...

    Abstract Synthetic cannabinoid receptor agonists (SCRAs) are the second largest class of new psychoactive substances (NPS) and are associated with serious adverse effects and even death. Despite this, little pharmacological data are available for many of the most recent SCRAs. This study consists of three different parts, aiming to systematically evaluate a panel of 30 SCRAs using binding and different in vitro human cannabinoid 1 receptor (CB
    MeSH term(s) Cannabinoid Receptor Agonists/chemical synthesis ; Cannabinoid Receptor Agonists/chemistry ; Cannabinoid Receptor Agonists/pharmacology ; Cannabinoids/chemical synthesis ; Cannabinoids/chemistry ; Cannabinoids/pharmacology ; Humans ; Indazoles/pharmacology ; Indoles/chemical synthesis ; Indoles/chemistry ; Indoles/pharmacology ; Receptor, Cannabinoid, CB1/agonists ; Structure-Activity Relationship ; beta-Arrestins/metabolism
    Chemical Substances 7-azaindole dimer ; Cannabinoid Receptor Agonists ; Cannabinoids ; Indazoles ; Indoles ; Receptor, Cannabinoid, CB1 ; beta-Arrestins
    Language English
    Publishing date 2021-04-14
    Publishing country England
    Document type Comparative Study ; Journal Article
    ZDB-ID 2462336-2
    ISSN 1942-7611 ; 1942-7603
    ISSN (online) 1942-7611
    ISSN 1942-7603
    DOI 10.1002/dta.3035
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    In stock of ZB MED Cologne/Königswinter

    Zs.A 6792: Show issues Location:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 2021: Bestellungen von Artikeln über das Online-Bestellformular
    ab Jg. 2022: Lesesaal (EG)

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  7. Article ; Online: Enantioselective (4+2) Annulation of Donor-Acceptor Cyclobutanes by N-Heterocyclic Carbene Catalysis.

    Levens, Alison / Ametovski, Adam / Lupton, David W

    Angewandte Chemie (International ed. in English)

    2016  Volume 55, Issue 52, Page(s) 16136–16140

    Abstract: Herein we report the enantioselective (4+2) annulation of donor-acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent ... ...

    Abstract Herein we report the enantioselective (4+2) annulation of donor-acceptor cyclobutanes and unsaturated acyl fluorides using N-heterocyclic carbene catalysis. The reaction allows a 3-step synthesis of cyclohexyl β-lactones (25 examples) in excellent chemical yield (most ≥90 %) and stereochemical integrity (all >20:1 d.r., most ≥97:3 e.r.). Mechanistic studies support ester enolate Claisen rearrangement, while derivatizations provide functionalized cyclohexenes and dihydroquinolinones.
    Language English
    Publishing date 2016--23
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201609330
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  8. Article ; Online: Structure-Activity Relationships, Deuteration, and Fluorination of Synthetic Cannabinoid Receptor Agonists Related to AKB48, 5F-AKB-48, and AFUBIATA.

    Sparkes, Eric / Maloney, Callan J / Markham, Jack W / Dane, Chianna / Boyd, Rochelle / Gilchrist, Jayson / Moir, Michael / Gordon, Rebecca / Luo, Jia Lin / Pike, Edward / Walker, Katelyn A / Kassiou, Michael / McGregor, Iain S / Kevin, Richard C / Hibbs, David E / Jorgensen, William T / Banister, Samuel D / Cairns, Elizabeth A / Ametovski, Adam

    ACS chemical neuroscience

    2024  

    Abstract: Synthetic cannabinoid receptor agonists (SCRAs) are a growing class of new psychoactive substances (NPS) commonly derived from ... ...

    Abstract Synthetic cannabinoid receptor agonists (SCRAs) are a growing class of new psychoactive substances (NPS) commonly derived from an
    Language English
    Publishing date 2024-05-20
    Publishing country United States
    Document type Journal Article
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.3c00850
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  9. Article: MEPIRAPIM-derived synthetic cannabinoids inhibit T-type calcium channels with divergent effects on seizures in rodent models of epilepsy.

    Harman, Thomas / Udoh, Michael / McElroy, Dan L / Anderson, Lyndsey L / Kevin, Richard C / Banister, Samuel D / Ametovski, Adam / Markham, Jack / Bladen, Chris / Doohan, Peter T / Greba, Quentin / Laprairie, Robert B / Snutch, Terrance P / McGregor, Iain S / Howland, John G / Arnold, Jonathon C

    Frontiers in physiology

    2023  Volume 14, Page(s) 1086243

    Abstract: Background: ...

    Abstract Background:
    Language English
    Publishing date 2023-04-04
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 2564217-0
    ISSN 1664-042X
    ISSN 1664-042X
    DOI 10.3389/fphys.2023.1086243
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  10. Article ; Online: Putative Synthetic Cannabinoids MEPIRAPIM, 5F-BEPIRAPIM (NNL-2), and Their Analogues Are T-Type Calcium Channel (Ca

    Kevin, Richard C / Mirlohi, Somayeh / Manning, Jamie J / Boyd, Rochelle / Cairns, Elizabeth A / Ametovski, Adam / Lai, Felcia / Luo, Jia Lin / Jorgensen, William / Ellison, Ross / Gerona, Roy R / Hibbs, David E / McGregor, Iain S / Glass, Michelle / Connor, Mark / Bladen, Chris / Zamponi, Gerald W / Banister, Samuel D

    ACS chemical neuroscience

    2022  Volume 13, Issue 9, Page(s) 1395–1409

    Abstract: Synthetic cannabinoid receptor agonists (SCRAs) are a large and growing class of new psychoactive substances (NPSs). Two recently identified compounds, MEPIRAPIM and 5F-BEPIRAPIM (NNL-2), have not been confirmed as agonists of either cannabinoid receptor ...

    Abstract Synthetic cannabinoid receptor agonists (SCRAs) are a large and growing class of new psychoactive substances (NPSs). Two recently identified compounds, MEPIRAPIM and 5F-BEPIRAPIM (NNL-2), have not been confirmed as agonists of either cannabinoid receptor subtype but share structural similarities with both SCRAs and a class of T-type calcium channel (Ca
    MeSH term(s) Animals ; Calcium Channels, T-Type ; Cannabinoid Receptor Agonists/pharmacology ; Cannabinoids/chemistry ; Cannabinoids/pharmacology ; Hypothermia ; Indazoles/pharmacology ; Mice ; Receptor, Cannabinoid, CB1 ; Receptor, Cannabinoid, CB2 ; Receptors, Cannabinoid
    Chemical Substances Calcium Channels, T-Type ; Cannabinoid Receptor Agonists ; Cannabinoids ; Indazoles ; Receptor, Cannabinoid, CB1 ; Receptor, Cannabinoid, CB2 ; Receptors, Cannabinoid
    Language English
    Publishing date 2022-04-20
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.1c00822
    Database MEDical Literature Analysis and Retrieval System OnLINE

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