OXAPROTILINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H23NO
Molecular Weight	293.4027
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC(O)CC12CCC(C3=CC=CC=C13)C4=CC=CC=C24

InChI

InChIKey=FDXQKWSTUZCCTM-UHFFFAOYSA-N

InChI=1S/C20H23NO/c1-21-13-14(22)12-20-11-10-15(16-6-2-4-8-18(16)20)17-7-3-5-9-19(17)20/h2-9,14-15,21-22H,10-13H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3527706 | https://www.ncbi.nlm.nih.gov/pubmed/1353628

Oxaprotiline (also known as hydroxymaprotiline) is a norepinephrine reuptake inhibitor and blocked the histamine H1 receptor. Oxaprotiline was studied in the treatment of hospitalized depressive patients. However, this drug has never been marketed.

CNS Activity

Approval Year

PubMed

Title	Date	PubMed
(+)-Oxaprotiline but not (-)-oxaprotiline given chronically potentiates the aggressive behaviour induced by clonidine.	1983 Mar	6132979
Oxaprotiline enantiomers given repeatedly and brain alpha-adrenoceptors.	1990	2158798
PET imaging of norepinephrine transporters.	2006	17073682
Modulation of electrically evoked serotonin release in cultured rat raphe neurons.	2007 Mar	17348865
Psychosocial determinants of recovery in depression.	2008	19170403

Patents

Name

Type

Language

OXAPROTILINE

Official Name

English

(±)-.ALPHA.-((METHYLAMINO)METHYL)-9,10-ETHANOANTHRACENE-9(10H)-ETHANOL

Systematic Name

English

Oxaprotiline [WHO-DD]

Common Name

English

oxaprotiline [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB09307