Chemistry:Metapramine

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Short description: Chemical compound
Metapramine
Metapramine skeletal.svg
Clinical data
Trade namesProdastene, Timaxel
Routes of
administration		Oral
ATC code
  • none
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life7–8 hours
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC16H18N2
Molar mass238.334 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture

Metapramine (brand names Prodastene, Timaxel) is a tricyclic antidepressant (TCA) developed by Rhone Poulenc[1] that was introduced for the treatment of depression in France in 1984.[2][3] In addition to its efficacy against affective disorders, it also has analgesic properties,[4][5] 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.[6][7][8] It has also been shown to act as a low-affinity NMDA receptor antagonist.[9] 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.[8][10]

References

  1. ↑ Fouche JC, Alexandre CG, "Dibenzazepine derivatives and their preparation", US patent 3622565, issued 23 November 1971, assigned to Rhone Poulenc SA
  2. ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 13. ISBN 0-412-54090-8. https://books.google.com/books?id=kfhQgpqxiVgC&q=metapramine&pg=PA13. 
  3. ↑ "Compounds launched in single countries". Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. 2007. p. 248. ISBN 978-3-527-31058-6. https://books.google.com/books?id=yXD4QA-Y_Z0C&q=metapramine&pg=PA248. 
  4. ↑ "Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants". Pain 31 (3): 391–400. December 1987. doi:10.1016/0304-3959(87)90167-9. PMID 2827090. 
  5. ↑ "Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties". Life Sciences 50 (3): 161–168. 1992. doi:10.1016/0024-3205(92)90268-T. PMID 1731171. 
  6. ↑ "[Effects, in rats, of metapramine and carpipramine on the uptake of catecholamines and serotonin; relationship with 3H-imipramine binding]" (in fr). Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales 180 (1): 43–48. 1986. PMID 3017518. 
  7. ↑ "Immediate effects of 14 non MAOI antidepressants in rats with spontaneous petit mal-like seizures". Progress in Neuro-Psychopharmacology & Biological Psychiatry 14 (2): 261–270. 1990. doi:10.1016/0278-5846(90)90106-q. PMID 2106711. 
  8. ↑ 8.0 8.1 "[Metapramine: antidepressant and psycho-stimulant]" (in fr). L'Encephale 2 (3): 219–223. 1976. PMID 1033059. 
  9. ↑ "The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors". Neuropharmacology 35 (12): 1703–1707. 1996. doi:10.1016/S0028-3908(96)00122-0. PMID 9076749. 
  10. ↑ "[Evaluation of the central anticholinergic activity of antidepressants. Comparison of two experimental methods]" (in fr). Annales Pharmaceutiques Françaises 47 (3): 135–141. 1989. PMID 2634929. 



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