Metapramine

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

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 (±)-10,11-dihydro-N,5-dimethyl-5H-dibenz[b,f]azepin-10-amine
CAS Number	21730-16-5
PubChem CID	65700
ChemSpider	59127
UNII	303954M7YF
Chemical and physical data
Formula	C16H18N2
Molar mass	238.334 g·mol^−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CNC1CC2=C(C=CC=C2)N(C)C3=CC=CC=C31

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. US Patent 3622565 - DIBENZAZEPINE DERIVATIVES AND THEIR PREPARATION
2. Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 13. ISBN 0-412-54090-8.
3. José Miguel Vela; Helmut Buschmann; Jörg Holenz; Antonio Párraga; Antoni Torrens (2007). 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, et al. (1992). "Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties". Life Sciences. 50 (3): 161–8. doi:10.1016/0024-3205(92)90268-T. PMID 1731171.
6. Dagonneau H, Fonlupt P, Pacheco H (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 (in French). 180 (1): 43–8. 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): 261–70. doi:10.1016/0278-5846(90)90106-q. PMID 2106711. S2CID 8332732.
8. Bonierbale M, Dufour H, Scotto JC, Sutter JM (1976). "[Metapramine: antidepressant and psycho-stimulant]". L'Encéphale (in French). 2 (3): 219–23. 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): 1703–7. doi:10.1016/S0028-3908(96)00122-0. PMID 9076749. S2CID 7244740.
10. Dufour P, Billa JP, Fabre J, Roquebert J (1989). "[Evaluation of the central anticholinergic activity of antidepressants. Comparison of two experimental methods]". Annales Pharmaceutiques Françaises (in French). 47 (3): 135–41. PMID 2634929.