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    Svetlana Velmar-Janković

    N-Methyl-3-piperidyl benzilate
    Legal status
    Legal status
    Identifiers
    • (1-Methylpiperidin-3-yl) 2-hydroxy-2,2-di(phenyl)acetate
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard100.020.031 Edit this at Wikidata
    Chemical and physical data
    FormulaC20H23NO3
    Molar mass325.408 g·mol−1
    3D model (JSmol)
    • O=C(OC1CCCN(C)C1)C(O)(c2ccccc2)c3ccccc3
    • InChI=1S/C20H23NO3/c1-21-14-8-13-18(15-21)24-19(22)20(23,16-9-4-2-5-10-16)17-11-6-3-7-12-17/h2-7,9-12,18,23H,8,13-15H2,1H3 checkY
    • Key:ZBEILXWHVSVDBN-UHFFFAOYSA-N checkY
      (verify)

    N-Methyl-3-piperidyl benzilate (JB-336 or LBJ) is an anticholinergic drug related to the chemical warfare agent 3-quinuclidinyl benzilate.

    N-methyl-3-piperidyl benzilate is less potent and shorter acting than 3-quinuclidyl benzilate, but like 3-QNB its effects on the central nervous system predominate over peripheral effects. It produces deliriant and hallucinogenic effects similar to those of plants such as datura and may be used recreationally at low doses; however, unpleasant side effects such as dysphoria, nausea and vomiting, dizziness and extreme dry mouth tend to make abuse of drugs of this kind uncommon. Both the N-methyl and N-ethyl analogues of 3-piperidyl benzilate are, however, Schedule I controlled drugs.

    Radiolabelled versions of this drug are used in scientific research to map the distribution of muscarinic acetylcholine receptors in the brain.[1]

    Reaction of JB-336 with methyl bromide gives the gastrointestinal drug Mepenzolate bromide.

    See also

    References

    1. ^ Takahashi K, Murakami M, Miura S, Iida H, Kanno I, Uemura K (March 1999). "Synthesis and autoradiographic localization of muscarinic cholinergic antagonist (+)N-[11C]methyl-3-piperidyl benzilate as a potent radioligand for positron emission tomography". Applied Radiation and Isotopes. 50 (3): 521–5. doi:10.1016/S0969-8043(97)10155-5. PMID 10070712.
    Credit: Wikipedia https://en.wikipedia.org/wiki/N-Methyl-3-piperidyl_benzilate

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