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
Psychosocial determinants of recovery in depression.	2008	19170403
Modulation of electrically evoked serotonin release in cultured rat raphe neurons.	2007-03	17348865
PET imaging of norepinephrine transporters.	2006	17073682
Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons.	2005-08-01	15914010
Comparative evaluation of positron emission tomography radiotracers for imaging the norepinephrine transporter: (S,S) and (R,R) enantiomers of reboxetine analogs ([11C]methylreboxetine, 3-Cl-[11C]methylreboxetine and [18F]fluororeboxetine), (R)-[11C]nisoxetine, [11C]oxaprotiline and [11C]lortalamine.	2005-07	15998285
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.	2001-02	11181434
Differential effects of the enantiomers R(-) and S(+) oxaprotiline on major endogenous depression, the sleep EEG and neuroendocrine secretion: studies on depressed patients and normal controls.	1993-06	8364347
Oxaprotiline enantiomers given repeatedly and brain alpha-adrenoceptors.	1990	2158798
The influence of oxaprotiline enantiomers given repeatedly on the behavioural effects of d-amphetamine and dopamine injected into the nucleus accumbens.	1988-01-12	3350045
(+)-Oxaprotiline but not (-)-oxaprotiline given chronically potentiates the aggressive behaviour induced by clonidine.	1983-03	6132979

Patents

Name

Type

Language

Oxaprotiline [WHO-DD]

Preferred Name

English

OXAPROTILINE

Official Name

English

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

Systematic Name

English

oxaprotiline [INN]

Common Name

English

Code System Code Type Description

DRUG BANK

DB09307