Demexiptiline

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Demexiptiline
Skeletal formula of demexiptiline
Space-filling model of the demexiptiline molecule
Clinical data
Trade namesDeparon, Tinoran
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life35 hours[1]
Identifiers
  • 5H-dibenzo(a,d)cyclohepten-5-one O-(2-(methylamino)ethyl)oxime
JSmol)
  • O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC

Demexiptiline (brand names Deparon, Tinoran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression.[2][3] It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine.[4]

Synthesis

The synthesis is similar to that reported for Noxiptiline but also differs in a couple of respects.

Synthesis:[5] Patents:[6][7]

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).

References

  1. ISBN 978-3-527-64565-7
    .
  2. ISBN 3-88763-075-0
    .
  3. ISBN 0-412-46630-9
    .
  4. S2CID 24240307
    .
  5. PMID 5819763
    .
  6. ^ US 3989844, Schütz S, Behner O, Hoffmeister F, issued 1976, assigned to Bayer AG.  & U.S. patent 3,963,778
  7. ^ DE 1247302, Schütz S, Behner O, Hoffmeister F, issued 1967, assigned 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.
    PMID 7337336
    .