Metapramine

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 (rac)-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;
CompTox Dashboard (EPA)	DTXSID60865011 ;
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 (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.