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Mu-opioid receptor agonists
Ciramadol
Другие языки:

    Ciramadol

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    Not to be confused with Cimaterol.
    Ciramadol
    Ciramadol.svg
    Clinical data
    Other names Ciramadol, WY-15705
    Routes of
    administration    		 Oral
    ATC code
    • none
    Identifiers
    • 3-{(R)-Dimethylamino-[(1R,2R)-2-hydroxycyclohexyl]}methyl]phenol
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    KEGG
    ChEMBL
    Chemical and physical data
    Formula C15H23NO2
    Molar mass 249.354 g·mol−1
    3D model (JSmol)
    • OC1=CC=CC([C@@H]([C@H]2CCCC[C@H]2O)N(C)C)=C1
    • InChI=1S/C15H23NO2/c1-16(2)15(11-6-5-7-12(17)10-11)13-8-3-4-9-14(13)18/h5-7,10,13-15,17-18H,3-4,8-9H2,1-2H3/t13-,14+,15-/m0/s1 checkY
    • Key:UVTLONZTPXCUPU-ZNMIVQPWSA-N checkY
      (verify)

    Ciramadol (WY-15,705) is an opioid analgesic that was developed in the late 1970s and is related to phencyclidine, tramadol, tapentadol and venlafaxine. It is a mixed agonist-antagonist for the μ-opioid receptor with relatively low abuse potential and a ceiling on respiratory depression which makes it a relatively safe drug. It has a slightly higher potency and effectiveness as an analgesic than codeine, but is weaker than morphine. Other side effects include sedation and nausea but these are generally less severe than with other similar drugs.

    Synthesis

    Ciramadol synthesis: Patents:

    The Claisen-Schmidt condensation between 3-(methoxymethoxy)benzaldehyde [13709-05-2] (1) and cyclohexanone (2) afforded CID:54364197 (3). Michael addition of dimethylamine leads the aminoketone, i.e. 2-[dimethylamino-[3-(methoxymethoxy)phenyl]methyl]cyclohexan-1-one, CID21518320. Reduction of the ketone proceeds stereospecifically to afford the cis aminoalcohol [51356-58-2] (4). Mild hydrolysis of the product gives the free phenol ciramadol (5).

    See also



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