METAPRAMINE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H18N2
Molecular Weight	238.3275
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC1CC2=CC=CC=C2N(C)C3=C1C=CC=C3

InChI

InChIKey=YXVZOBVWVRFPTE-UHFFFAOYSA-N

InChI=1S/C16H18N2/c1-17-14-11-12-7-3-5-9-15(12)18(2)16-10-6-4-8-13(14)16/h3-10,14,17H,11H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C16H18N2
Molecular Weight	238.3275
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9076749 | https://www.ncbi.nlm.nih.gov/pubmed/3017518 | https://www.ncbi.nlm.nih.gov/pubmed/1033059 | https://www.ncbi.nlm.nih.gov/pubmed/2872367 | (1980) Psychopharmacology Bulletin, page 8, retrieved from: https://books.google.ru/books?id=Wwa2VEl3iuQC

Metapramine is a tetracyclic antidepressant available in tablet and injectable form. It is claimed to have an antidepressant effect and is useful in all types of depression. Metapramine is a low-affinity antagonist of the NMDA receptor complex channel. Its acting as a norepinephrine reuptake inhibitor without affecting the reuptake of serotonin and dopamine. Quick acting, metapramine has a very interesting peculiarity: its large tolerance, which seems to be related to a no-anticholinergic effect. Metapramine could be indicated for correction of extra-pyramidal side effects induced by neuroleptics or observed in parkinsonism.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Glutamate NMDA receptor 47 Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9076749	Antagonist 2849		1.8 µM [IC50]
norepinephrine uptake 18 Target ID: GO:0051620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3017518	Inhibitor 8504

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:48:32 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:32 GMT 2025`
Record UNII	303954M7YF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METAPRAMINE [MI]

Preferred Name

English

METAPRAMINE

Official Name

English

10,11-DIHYDRO-5-METHYL-10-(METHYLAMINO)-5H-DIBENZ(B,F)AZEPINE

Systematic Name

English

metapramine [INN]

Common Name

English

Metapramine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265