Metapramine
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Trade names | Prodastene, Timaxel |
| Routes of administration | Oral |
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| Elimination half-life | 7–8 hours |
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| Formula | C16H18N2 |
| Molar mass | 238.334 g·mol−1 |
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| Chirality | Racemic mixture |
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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]
Synthesis
A pair of syntheses has been reported in the patent literature:[11][1]
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).