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Metapramine

Clinical data
Trade names	Prodastene, Timaxel
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Elimination half-life	7–8 hours
Identifiers
IUPAC name (rac)-10,11-dihydro-N,5-dimethyl-5H-dibenzazepin-10-amine
CAS Number	21730-16-5
PubChem CID	65700
ChemSpider	59127
UNII	303954M7YF
CompTox Dashboard (EPA)	DTXSID60865011
Chemical and physical data
Formula	C16H18N2
Molar mass	238.334 g·mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CNC1CC2=C(C=CC=C2)N(C)C3=CC=CC=C31

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.

References

1. US 3622565, Fouche JC, Alexandre CG, "Dibenzazepine derivatives and their preparation", 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.
3. Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A (2007). "Compounds launched in single countries". Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application. Weinheim: Wiley-VCH. p. 248. ISBN 978-3-527-31058-6.
4. Michael-Titus A, Costentin J (December 1987). "Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants". Pain. 31 (3): 391–400. doi:10.1016/0304-3959(87)90167-9. PMID 2827090. S2CID 39569622.
5. Fialip J, Marty H, Aumaitre O, Bougerolle AM, Dordain G, Berger JA, Eschalier A (1992). "Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties". Life Sciences. 50 (3): 161–168. doi:10.1016/0024-3205(92)90268-T. PMID 1731171.
6. Dagonneau H, Fonlupt P, Pacheco H (1986). "". Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales (in French). 180 (1): 43–48. PMID 3017518.
7. Warter JM, Tranchant C, Marescaux C, Depaulis A, Lannes B, Vergnes M (1990). "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. doi:10.1016/0278-5846(90)90106-q. PMID 2106711. S2CID 8332732.
8. ^ Bonierbale M, Dufour H, Scotto JC, Sutter JM (1976). "". L'Encephale (in French). 2 (3): 219–223. PMID 1033059.
9. Boireau A, Bordier F, Durand G, Doble A (1996). "The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors". Neuropharmacology. 35 (12): 1703–1707. doi:10.1016/S0028-3908(96)00122-0. PMID 9076749. S2CID 7244740.
10. Dufour P, Billa JP, Fabre J, Roquebert J (1989). "". Annales Pharmaceutiques Françaises (in French). 47 (3): 135–141. PMID 2634929.

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