Metapramine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = (rac)-10,11-dihydro-N,5-dimethyl-5H-dibenz[b,f]azepin-10-amine

| image = Metapramine skeletal.svg

| width = 200px

| tradename = Prodastene, Timaxel

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life = 7–8 hours

| excretion =

| CAS_number = 21730-16-5

| ATC_prefix = none

| ATC_suffix =

| PubChem = 65700

| ChemSpiderID = 59127

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 303954M7YF

| C=16 | H=18 | N=2

| SMILES = CNC1CC2=C(C=CC=C2)N(C)C3=CC=CC=C31

| chirality = Racemic mixture

}}

Metapramine (brand names Prodastene, Timaxel) is a tricyclic antidepressant (TCA) developed by Rhone Poulenc{{cite patent | country = US | number = 3622565 | title = Dibenzazepine derivatives and their preparation | inventor = Fouche JC, Alexandre CG | assign1 = Rhone Poulenc SA | gdate = 23 November 1971 | url = https://patents.google.com/patent/US3622565A/en?oq=US+Patent+3622565 }} that was introduced for the treatment of depression in France in 1984.{{cite book | title = Dictionary of organic compounds | publisher = Chapman & Hall | location = London | year = 1996 | page = 13 | isbn = 0-412-54090-8 | url = https://books.google.com/books?id=kfhQgpqxiVgC&q=metapramine&pg=PA13}}{{cite book | vauthors = Vela JM, Buschmann H, Holenz J, Párraga A, Torrens A | chapter = Compounds launched in single countries | title = Antidepressants, Antipsychotics, Anxiolytics: From Chemistry and Pharmacology to Clinical Application | publisher = Wiley-VCH | location = Weinheim | year = 2007 | page = 248 | isbn = 978-3-527-31058-6 | chapter-url = https://books.google.com/books?id=yXD4QA-Y_Z0C&q=metapramine&pg=PA248}} In addition to its efficacy against affective disorders, it also has analgesic properties,{{cite journal | vauthors = Michael-Titus A, Costentin J | title = Analgesic effects of metapramine and evidence against the involvement of endogenous enkephalins in the analgesia induced by tricyclic antidepressants | journal = Pain | volume = 31 | issue = 3 | pages = 391–400 | date = December 1987 | pmid = 2827090 | doi = 10.1016/0304-3959(87)90167-9 | s2cid = 39569622 }}{{cite journal | vauthors = Fialip J, Marty H, Aumaitre O, Bougerolle AM, Dordain G, Berger JA, Eschalier A | title = Antinociceptive activity of metapramine in mice. Relationship with its pharmacokinetic properties | journal = Life Sciences | volume = 50 | issue = 3 | pages = 161–168 | year = 1992 | pmid = 1731171 | doi = 10.1016/0024-3205(92)90268-T }} 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.{{cite journal | vauthors = Dagonneau H, Fonlupt P, Pacheco H | title = [Effects, in rats, of metapramine and carpipramine on the uptake of catecholamines and serotonin; relationship with 3H-imipramine binding] | language = fr | journal = Comptes Rendus des Séances de la Société de Biologie et de Ses Filiales | volume = 180 | issue = 1 | pages = 43–48 | year = 1986 | pmid = 3017518 }}{{cite journal | vauthors = Warter JM, Tranchant C, Marescaux C, Depaulis A, Lannes B, Vergnes M | title = Immediate effects of 14 non MAOI antidepressants in rats with spontaneous petit mal-like seizures | journal = Progress in Neuro-Psychopharmacology & Biological Psychiatry | volume = 14 | issue = 2 | pages = 261–270 | year = 1990 | pmid = 2106711 | doi = 10.1016/0278-5846(90)90106-q | s2cid = 8332732 }}{{cite journal | vauthors = Bonierbale M, Dufour H, Scotto JC, Sutter JM | title = [Metapramine: antidepressant and psycho-stimulant] | language = fr | journal = L'Encephale | volume = 2 | issue = 3 | pages = 219–223 | year = 1976 | pmid = 1033059 }} It has also been shown to act as a low-affinity NMDA receptor antagonist.{{cite journal | vauthors = Boireau A, Bordier F, Durand G, Doble A | title = The antidepressant metapramine is a low-affinity antagonist at N-methyl-D-aspartic acid receptors | journal = Neuropharmacology | volume = 35 | issue = 12 | pages = 1703–1707 | year = 1996 | pmid = 9076749 | doi = 10.1016/S0028-3908(96)00122-0 | s2cid = 7244740 }} 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.{{cite journal | vauthors = Dufour P, Billa JP, Fabre J, Roquebert J | title = [Evaluation of the central anticholinergic activity of antidepressants. Comparison of two experimental methods] | language = fr | journal = Annales Pharmaceutiques Françaises | volume = 47 | issue = 3 | pages = 135–141 | year = 1989 | pmid = 2634929 }}