Metapramine
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Systematic (IUPAC) name | |
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(±)-10,11-dihydro-N,5-dimethyl-5H-dibenz[b,f]azepin-10-amine | |
Clinical data | |
Routes of administration | Oral |
Legal status | |
Legal status |
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Pharmacokinetic data | |
Biological half-life | 7-8 hours |
Identifiers | |
CAS Number | 21730-16-5 |
ATC code | none |
PubChem | CID 65700 |
ChemSpider | 59127 |
Chemical data | |
Formula | C16H18N2 |
Molar mass | 238.33 g/mol[[Script error: No such module "String".]] |
Metapramine (trade name Timaxel) is a tricyclic antidepressant (TCA) which was introduced for the treatment of depression in France in 1984.[1][2] In addition to its efficacy against affective disorders, it also has analgesic properties,[3][4] 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.[5][6][7] It has also been shown to act as a low-affinity NMDA receptor antagonist.[8] 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.[9][7]
See also
References
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GABAA PAMs |
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α2δ VDCC Blockers | |||||||||||
5-HT1A Agonists | |||||||||||
H1 Antagonists | Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine • Pheniramine | ||||||||||
CRH1 Antagonists | |||||||||||
NK2 Antagonists | |||||||||||
MCH1 antagonists | |||||||||||
mGluR2/3 Agonists | |||||||||||
mGluR5 NAMs | |||||||||||
TSPO agonists | |||||||||||
σ1 agonists | |||||||||||
Others | Benzoctamine • Carbetocin • Demoxytocin • Mephenoxalone • Mepiprazole • Oxanamide • Oxytocin • Promoxolane • Tofisopam • Trimetozine • WAY-267,464 | ||||||||||
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Opioids See also: Opioids template |
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Cannabinoids | |||||||||||||
Anilides | |||||||||||||
Non-steroidal anti-inflammatories See also: NSAIDs template |
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Atypical, Adjuvant & Potentiators, Metabolic agents and miscellaneous | Amitryptiline · Befiradol · Bicifadine · Carisoprodol · Camphor · Cimetidine · Clonidine · Chlorzoxazone · Cyclobenzaprine · Duloxetine · Esreboxetine · Flupirtine · Gabapentin · Glafenine · Hydroxyzine · Ketamine · Menthol · Mephenoxalone · Methocarbamol · Nefopam · Orphenadrine · Pregabalin · Proglumide · Scopolamine · Tebanicline · Trazodone · XP-13512 (Gabapentin enacarbil) · Ziconotide | ||||||||||||
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Ionotropic |
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Metabotropic |
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Transporter inhibitors |
Classes | |
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Antidepressants | 7-OH-Amoxapine • Amezepine • Amineptine • Amitriptyline • Amitriptylinoxide • Amoxapine • Aptazapine • Azepindole • Azipramine • Butriptyline • Cianopramine • Ciclazindol • Ciclopramine • Clomipramine • Cotriptyline • Cyanodothiepin • Demexiptiline • Depramine/Balipramine • Desipramine • Dibenzepine • Dimetacrine • Dosulepin/Dothiepin • Doxepin • Enprazepine • Esmirtazapine • Fluotracen • Hepzidine • Homopipramol • Imipramine • Imipraminoxide • Intriptyline • Iprindole • Ketipramine • Litracen • Lofepramine • Losindole • Loxapine • Maprotiline • Mariptiline • Mazindol • Melitracen • Metapramine • Mezepine • Mianserin • Mirtazapine • Naranol • Nitroxazepine • Nortriptyline • Noxiptiline • Octriptyline • Opipramol • Oxaprotiline • Pipofezine • Pirandamine • Propizepine • Protriptyline • Quinupramine • Setiptiline/Teciptiline • Tandamine • Tampramine • Tianeptine • Tienopramine • Trimipramine |
Antihistamines | Alimemazine • Azatadine • Clobenzepam • Cyproheptadine • Dacemazine • Deptropine • Desloratadine • Epinastine • Etymemazine • Hydroxyethylpromethazine • Isopromethazine • Isothipendyl • Ketotifen • Latrepirdine • Loratadine • Mebhydrolin • Mequitazine • Methdilazine • Olopatadine • Oxomemazine • Phenindamine • Pimethixene • Promethazine • Propiomazine • Rupatadine • Thiazinamium |
Antipsychotics | Acetophenazine • Amoxapine • Asenapine • Butaclamol • Butaperazine • Carphenazine • Carpipramine • Chlorpromazine • Chlorprothixene • Ciclindole • Clocapramine • Clomacran • Clotiapine • Clozapine • Flucindole • Fluotracen • Flupentixol • Fluphenazine • Gevotroline • Homopipramol • Levomepromazine/Methotrimeprazine • Loxapine • Maroxepin • Mesoridazine • Metitepine/Methiothepin • Metoxepin • Mosapramine • Naranol • Olanzapine • Perazine • Perphenazine • Periciazine • Piperacetazine • Pipotiazine • Piquindone • Prochlorperazine • Promazine • Prothipendyl • Quetiapine • Sulforidazine • Thiethylperazine • Thiopropazate • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Zotepine • Zuclopenthixol |
Others |
- ↑ Dictionary of organic compounds. London: Chapman & Hall. 1996. p. 13. ISBN 0-412-54090-8.
- ↑ 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 3-527-31058-4. More than one of
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- ↑ 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. PMID 1731171. CS1 maint: Explicit use of et al. (link) CS1 maint: Multiple names: authors list (link)
- ↑ 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. CS1 maint: Multiple names: authors list (link) CS1 maint: Unrecognized language (link)
- ↑ 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. PMID 2106711. CS1 maint: Multiple names: authors list (link)
- ↑ 7.0 7.1 Bonierbale M, Dufour H, Scotto JC, Sutter JM (1976). "[Metapramine: antidepressant and psycho-stimulant]". L'Encéphale (in French). 2 (3): 219–23. PMID 1033059. CS1 maint: Multiple names: authors list (link) CS1 maint: Unrecognized language (link)
- ↑ 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. PMID 9076749. CS1 maint: Multiple names: authors list (link)
- ↑ 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. CS1 maint: Multiple names: authors list (link) CS1 maint: Unrecognized language (link)
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