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Systematic (IUPAC) name
3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)- N,N-dimethyl-propan-1-amine N-oxide
CAS number 6829-98-7
ATC code  ?
PubChem 65589
ChemSpider 59031
Chemical data
Formula C19H24N2O
Mol. mass 296.41 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes Oral

Imipraminoxide (Imiprex, Elepsin), or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression. [1] [2][3][4]

Imipraminoxide is both an analogue and a metabolite of imipramine, and has similar effects.[5] [6][7] [8] However, in clinical trials, imipraminoxide was found to have a faster onset of action, slightly higher efficacy, and fewer and less marked side effects, including diminished orthostatic hypotension and anticholinergic effects like dry mouth, sweating, dizziness, and fatigue.[5] [6][7] [8][9][10]

Imipraminoxide's pharmacology has not been studied, but based on its very close relationship with imipramine, it likely acts as a serotonin and norepinephrine reuptake inhibitor and serotonin, adrenenaline, histamine, and muscarinic acetylcholine receptor antagonist, though with weaker antiadrenergic and anticholinergic actions.[9][10]

See also


  1. ^ "Index nominum, international drug … - Google Books".  
  2. ^ "Dictionary of organic compounds - Google Books".  
  3. ^ FAURBYE A, JACOBSEN O, KRISTJANSEN P, MUNKVAD I (September 1963). "Imipramine-N-oxide: preliminary investigation of a new antidepressive drug". The American Journal of Psychiatry 120: 277–8. PMID 13944543.  
  4. ^ Lingjaerde O (November 1971). "[Imiprex "Dumex" (imipramine oxide). A new tricyclic antidepressive agent]" (in Norwegian). Tidsskrift for Den Norske Lægeforening : Tidsskrift for Praktisk Medicin, Ny Række 91 (31): 2267–8. PMID 5133241.  
  5. ^ a b Rapp W, Norén MB, Pedersen F (1973). "Comparative trial of imipramine N-oxide and imipramine in the treatment of out-patients with depressive syndromes". Acta Psychiatrica Scandinavica 49 (1): 77–90. PMID 4572170.  
  6. ^ a b "Meyler's Side Effects of Psychiatric … - Google Books".  
  7. ^ a b 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. ^ a b "Wilson and Gisvold's textbook of … - Google Books".  
  9. ^ a b Dencker SJ, Bake B (July 1976). "Investigation of the orthostatic reaction after intravenous administration of imipramine, chlorimipramine, and inimpramine-N-oxide". Acta Psychiatrica Scandinavica 54 (1): 74–8. PMID 952235.  
  10. ^ a b Clemmesen L, Mikkelsen PL, Lund H, Bolwig TG, Rafaelsen OJ (1984). "Assessment of the anticholinergic effects of antidepressants in a single-dose cross-over study of salivation and plasma levels". Psychopharmacology 82 (4): 348–54. PMID 6427827.  

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