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Metapramine

Chemical compound

Metapramine

Chemical compound

| elimination_half-life = 7–8 hours

Metapramine (brand names Prodastene, Timaxel) is a tricyclic antidepressant (TCA) developed by Rhone Poulenc that was introduced for the treatment of depression in France in 1984. In addition to its efficacy against affective disorders, it also has analgesic properties, and may be useful in the treatment of pain.

Metapramine has desipramine-like effects, acting as a norepinephrine reuptake inhibitor without affecting the reuptake of serotonin or dopamine. It has also been shown to act as a low-affinity NMDA receptor antagonist. Metapramine's direct effects on serotonin, histamine, and muscarinic acetylcholine receptors have not been assayed, but uniquely among most TCAs, it has anecdotally been reported to lack anticholinergic effects.

Synthesis

A pair of syntheses has been reported in the patent literature:

The hydroboration between iminostilbene (1) and N,N-diethylaminoborane (2) gives 10-borohydro-5-methyl-10,11-dihydro-dibenzo[b,f]azepine (3). This is treated with methylchloramine (4), completing the synthesis of metapramine (5).

References

References

  1. "Dibenzazepine derivatives and their preparation".
  2. (1996). "Dictionary of organic compounds". Chapman & Hall.
  3. (2007). "Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application". Wiley-VCH.
  4. (December 1987). "Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants". Pain.
  5. (1992). "Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties". Life Sciences.
  6. (1986). "[Effects, in rats, of metapramine and carpipramine on the uptake of catecholamines and serotonin; relationship with 3H-imipramine binding]". Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales.
  7. (1990). "Immediate effects of 14 non MAOI antidepressants in rats with spontaneous petit mal-like seizures". Progress in Neuro-Psychopharmacology & Biological Psychiatry.
  8. (1976). "[Metapramine: antidepressant and psycho-stimulant]". L'Encephale.
  9. (1996). "The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors". Neuropharmacology.
  10. (1989). "[Evaluation of the central anticholinergic activity of antidepressants. Comparison of two experimental methods]". Annales Pharmaceutiques Françaises.
  11. Linares Hubert, GB1323219 (1973 to Rhone-poulenc S.a., Paris).
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dibenzazepines tricyclic-antidepressants
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