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Trimethobenzamide
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    Trimethobenzamide

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    Trimethobenzamide
    Trimethobenzamide2DACS.svg
    Trimethobenzamidefinal.png
    Clinical data
    Trade names Tigan, Tebamide
    AHFS/Drugs.com Monograph
    MedlinePlus a682693
    Routes of
    administration
    Oral, rectal, intramuscular
    ATC code
    Legal status
    Legal status
    Pharmacokinetic data
    Bioavailability 60-100%
    Elimination half-life 7 to 9 hours (mean)
    Excretion urine (30-50%), faeces
    Identifiers
    • N-{[4-(2-dimethylaminoethoxy)phenyl]methyl}-
      3,4,5-trimethoxy-benzamide
    CAS Number
    PubChem CID
    IUPHAR/BPS
    DrugBank
    ChemSpider
    UNII
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.004.848
    Chemical and physical data
    Formula C21H28N2O5
    Molar mass 388.464 g·mol−1
    3D model (JSmol)
    • O=C(c1cc(OC)c(OC)c(OC)c1)NCc2ccc(OCCN(C)C)cc2
    • InChI=1S/C21H28N2O5/c1-23(2)10-11-28-17-8-6-15(7-9-17)14-22-21(24)16-12-18(25-3)20(27-5)19(13-16)26-4/h6-9,12-13H,10-11,14H2,1-5H3,(H,22,24) checkY
    • Key:FEZBIKUBAYAZIU-UHFFFAOYSA-N checkY
     ☒NcheckY (what is this?)  (verify)

    Trimethobenzamide (trade names Tebamide, Tigan) is an antiemetic used to prevent nausea and vomiting.

    Mechanism of action

    Trimethobenzamide is an antagonist of the D2 receptor. It is believed to affect the chemoreceptor trigger zone (CTZ) of the medulla oblongata to suppress nausea and vomiting.

    Side effects

    Possible side effects include drowsiness, dizziness, headache, muscle cramps, and blurred vision. More serious adverse effects include skin rash, tremors, parkinsonism, and jaundice.

    Formulations

    Trimethobenzamide is marketed under the brand names Tebamide and Tigan, manufactured by GlaxoSmithKline and King Pharmaceuticals, respectively. It is available as oral capsules and injectable formulations.

    Trimethobenzamide was also available as a rectal suppository, but such formulations were banned by the U.S. Food and Drug Administration on April 6, 2007, due to unproven efficacy.

    Synthesis

    Trimethobenzamide synthesis: Hoffmann La Roche, U.S. Patent 2,879,293 (1959).

    Alkylation of the sodium salt of p-hydroxybenzaldehyde (1) with 2-dimethylaminoethyl chloride affords the ether (2). Reductive amination of the aldehyde in the presence of ammonia gives diamine (3). Acylation of that product with 3,4,5-trimethoxybenzoyl chloride affords trimethobenzamide (4).

    See also

    External links


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