The synthesis is similar to that reported for Noxiptiline but also differs in a couple of respects.
The condensation between Dibenzosuberenone [2222-33-5] (1) and hydroxylamine (2) gives the oxime, [1021-91-6] (3). Base catalyzed attachment of the sidechain by reaction with 2-Chloro-N-Methylethanamine [32315-92-7] (4) completed the synthesis of demexiptiline (5).
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↑ Teste JF, Pelsy-Johann I, Decelle T, Boulu RG (1993). "Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice". Fundamental & Clinical Pharmacology. 7 (5): 219–26. doi:10.1111/j.1472-8206.1993.tb00235.x. PMID8370568. S2CID24240307.
↑ Aichinger G, Behner O, Hoffmeister F, Schütz S. Basische tricyclische Oxyiminoäther und ihre pharmakologischen Eigenschaften [Basic tricyclic oxyiminoethers and their pharmacological properties]. Arzneimittelforschung. 1969 Jun;19:Suppl 5a:838+. German. PMID: 5819763.
↑ Dr Sigismund Schuetz, Dr Otto Behner, Dr Friedrich Hoffmeister, DE 1247302 (1967 to Bayer Ag).
Further reading
Martin A, Masson JM, Jusseaume P, Beloncle M, Voisinet C (November 1981). "[Demexiptiline in the treatment of melancholic states (reflections after 3 years of use)]". Annales médico-psychologiques (in French). 139 (9): 1023–35. PMID7337336.
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