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Systematic (IUPAC) name
3-(10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-ylidene)- N,N-dimethyl-1-propanamine N-oxide
CAS number 4317-14-0
ATC code  ?
PubChem 20313
ChemSpider 19137
Chemical data
Formula C20H23NO
Mol. mass 293.40 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Oral

Amitriptylinoxide (Amioxid, Ambivalon, Equilibrin), or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) that 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.[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][3][4] [5][6][7]

In receptor binding assays, amitripylinoxide 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.[3][8][9]

See also


  1. ^ "Index nominum, international drug … - Google Books".  
  2. ^ a b Rapp W (September 1978). "Comparative trial of amitriptyline-N-oxide and amitriptyline in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica 58 (3): 245–55. PMID 360779.  
  3. ^ a b c d Tegeler J, Klieser E, Lehmann E, Heinrich K (January 1990). "Double-blind study of the therapeutic efficacy and tolerability of amitriptylinoxide in comparison with amitriptyline". Pharmacopsychiatry 23 (1): 45–9.  
  4. ^ a b Godt HH, Fredslund-Andersen K, Edlund AH (1971). "[Amitriptyline N-oxide. A new antidepressant. A clinical double-blind trial in comparison with amitriptyline]" (in Danish). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 25 (3): 237–46. PMID 4945956.  
  5. ^ a b "Meyler's Side Effects of Psychiatric … - Google Books".  
  6. ^ Jensen PS, Bolwig T (1969). "[DANO (amitriptyline-N-oxide). A new antidepressive agent. A study with special reference to cardiotoxic effect]" (in Danish). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 23 (1): 30–5. PMID 5354541.  
  7. ^ Dencker SJ (1971). "[Clinical trial with imipramine-N-oxide and amitriptyline-N-oxide]" (in Swedish). Nordisk Psykiatrisk Tidsskrift. Nordic Journal of Psychiatry 25 (5): 463–70. PMID 4947298.  
  8. ^ Maj J, Vetulani J, Michaluk J, Rogóz Z, Skuza G (November 1982). "Central action of amitriptyline N-oxide". Pharmacopsychiatria 15 (6): 187–91. PMID 6185962.  
  9. ^ Hyttel J, Christensen AV, Fjalland B (July 1980). "Neuropharmacological properties of amitriptyline, nortriptyline and their metabolites". Acta Pharmacologica Et Toxicologica 47 (1): 53–7. PMID 7395525.  

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