Amitriptylinoxide

Legal statusLegal status IdentifiersCAS NumberPubChem CIDDrugBankChemSpiderUNIIKEGGChEBIChEMBLCompTox Dashboard (EPA)ECHA InfoCard100.119.550 Chemical and physical dataFormulaC₂₀H₂₃NOMolar mass293.410 g·mol⁻¹3D model (JSmol)  (verify)

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin), or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.^[1]

Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant.^[2][3][4][5] However, it has a faster onset of action and fewer adverse effects, including reduced drowsiness, sedation, anticholinergic symptoms like dry mouth, sweating, and dizziness, orthostatic hypotension, and cardiotoxicity.^{[2][3][4][5][6][7]}

In receptor binding assays, amitriptylinoxide was found to have generally equivalent pharmacology to amitriptyline, acting as a serotonin and norepinephrine reuptake inhibitor, serotonin receptor antagonist, and H₁ receptor antagonist, among other properties, but with approximately 60-fold lower affinity for the α₁-adrenergic receptor, and the weakest affinity of any of the TCAs analyzed for the muscarinic acetylcholine receptors.^[8][9][10]

Amitriptylinoxide has been said to be a prodrug of amitriptyline.^[11]

See also

• Imipraminoxide

References