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

Molecular Formula	C20H23NO
Molecular Weight	293.4027
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/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
The influence of oxaprotiline enantiomers given repeatedly on the behavioural effects of d-amphetamine and dopamine injected into the nucleus accumbens.	1988 Jan 12	3350045
Oxaprotiline enantiomers given repeatedly and brain alpha-adrenoceptors.	1990	2158798
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 Jun	8364347
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.	2001 Feb	11181434
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 Jul	15998285

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:38:42 UTC 2023` Edited by `admin` on `Fri Dec 15 18:38:42 UTC 2023`
Record UNII	3V3Z2HK4LS
Record Status	`Validated (UNII)`
Record Version

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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