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metapramine
Sign in to saveMetapramine (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.
Chemical data
- Formula
- C16H18N2
- Molecular weight
- 238.33 g/mol
- IUPAC name
- N,11-dimethyl-5,6-dihydrobenzo[b][1]benzazepin-5-amine
- SMILES
- CNC1CC2=CC=CC=C2N(C3=CC=CC=C13)C
- InChIKey
- YXVZOBVWVRFPTE-UHFFFAOYSA-N
- XLogP
- 3
- Polar surface area
- 15.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
42 papers- [Metapramine: antidepressant and psycho-stimulant].L'Encephale · 1976
- Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties.Life sciences · 1992
- Pharmacokinetics of metapramine (19560 RP) in man after infusion and intravenous injection.European journal of clinical pharmacology · 1983
- High-performance liquid chromatographic method for the determination of plasma and urine metapramine after dansylation.Journal of chromatography · 1982
- Kinetics of metapramine and its demethylated metabolites after single and chronic oral administration in man.European journal of drug metabolism and pharmacokinetics · 1986
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 238.147
Show 3 more facts
- canonical SMILES
- CNC1CC2=CC=CC=C2N(C3=CC=CC=C13)C
- chemical formula
- C₁₆H₁₈N₂
- subject has role
- tricyclic antidepressant
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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:
Excerpted from Wikipedia’s “metapramine” article, available under the CC BY-SA 4.0 licence.
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