Metapramine

Metapramine
Clinical data

Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Biological half-life	7-8 hours
Identifiers
IUPAC name (±)-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
Chemical and physical data
Formula	C₁₆H₁₈N₂
Molar mass	238.33 g/mol
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CNC1CC2=C(C=CC=C2)N(C)C3=CC=CC=C31

Metapramine (trade 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.

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