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    Potential Drug Abuse Therapeutics Derived from the Hallucinogenic Natural Product Salvinorin A

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    Prisinzano_2011.pdf (963.7Kb)
    Issue Date
    2011-12
    Author
    Prevatt-Smith, Katherine M.
    Lovell, Kimberly M.
    Simpson, Denise S.
    Day, Victor W.
    Douglas, Justin T.
    Bosch, Peter
    Dersch, Christina M.
    Rothman, Richard B.
    Kivell, Bronwyn
    Prisinzano, Thomas E.
    Publisher
    Royal Society of Chemistry
    Type
    Article
    Article Version
    Scholarly/refereed, author accepted manuscript
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    Abstract
    Previous structure-activity relationship studies of salvinorin A have shown that modification of the acetate functionality off the C-2 position to a methoxy methyl or methoxy ethyl ether moiety leads to increased potency at KOP receptors. However, the reason for this increase remains unclear. Here we report our efforts towards the synthesis and evaluation of C-2 constrained analogs of salvinorin A. These analogs were evaluated at opioid receptors in radioligand binding experiments as well as in the GTP-γ-S functional assay. One compound, 5, was found to have affinity and potency at κ opioid (KOP) receptors comparable to salvinorin A. In further studies, 5 was found to attenuate cocaine-induced drug seeking behavior in rats comparably to salvinorin A. This finding represents the first example of a salvinorin A analog that has demonstrated anti-addictive capabilities.
    URI
    http://hdl.handle.net/1808/24574
    DOI
    https://doi.org/10.1039/C1MD00192B.
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    • Medicinal Chemistry Scholarly Works [245]
    Citation
    Prevatt-Smith, K. M., Lovell, K. M., Simpson, D. S., Day, V. W., Douglas, J. T., Bosch, P., … Prisinzano, T. E. (2011). Potential Drug Abuse Therapeutics Derived from the Hallucinogenic Natural Product Salvinorin A. MedChemComm, 2(12), 1217–1222. http://doi.org/10.1039/C1MD00192B

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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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