INDELOXAZINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H17NO2
Molecular Weight	231.2903
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(OC1=C2CC=CC2=CC=C1)C3CNCCO3

InChI

InChIKey=MADRVGBADLFHMO-UHFFFAOYSA-N

InChI=1S/C14H17NO2/c1-3-11-4-2-6-14(13(11)5-1)17-10-12-9-15-7-8-16-12/h1-4,6,12,15H,5,7-10H2

HIDE SMILES / InChI

Molecular Formula	C14H17NO2
Molecular Weight	231.2903
Charge	0
Count

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

Description
Sources: http://apps.who.int/medicinedocs/index/assoc/h5778e/h5778e.pdf
Curator's Comment: description was created based on several sources, including: http://pmmp.cnki.net/Resources/CDDPdf/med%5Cbase%5C%E7%A5%9E%E7%BB%8F%E7%B3%BB%E7%BB%9F%E8%8D%AF%E7%89%A9%5C5795.pdf | https://www.ncbi.nlm.nih.gov/pubmed/518676 |https://www.reddit.com/r/Nootropics/comments/17qpe4/indeloxazine_information/

Indeloxazine is a neuroleptic, originally developed and marketed in Japan. It is indicated to allay autonomic hyperactivity following cerebral infarction, cerebral haemorrhage or atherosclerosis. It was found to be a weak inhibitor of both type A and type B monoamine oxidases. Indeloxazine-induced facilitation of acetylcholine release in frontal cortex is mediated by endogenous 5-HT and involves at least in part cortical 5-HT4 receptors. As a potential teratogen, Indeloxazine must not be consumed or handled by pregnant or nursing women, or by women who might become pregnant. It was removed from the market reportedly for lack of effectiveness.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase B 72 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/518676	Inhibitor 8297	260.0 µM [IC50]
Monoamine oxidase A 49 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/518676	Inhibitor 8297	90.0 µM [IC50]
Serotonin 4 (5-HT4) receptor 39 Target ID: CHEMBL4317 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9453456	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Cerebral infarction 14 Sources: http://apps.who.int/medicinedocs/index/assoc/h5778e/h5778e.pdf	Palliative	Withdrawn	Elen Approved Use Indeloxazine was commonly used to treat a psychiatric symptoms, such as memory impairment or emotional disturbance associated with a cerebral infarction, hemorrhage or cerebral arteriosclerosis.
Cerebral hemorrhage 4 Sources: http://apps.who.int/medicinedocs/index/assoc/h5778e/h5778e.pdf	Palliative	Withdrawn	Elen Approved Use Indeloxazine was commonly used to treat a psychiatric symptoms, such as memory impairment or emotional disturbance associated with a cerebral infarction, hemorrhage or cerebral arteriosclerosis.
Atherosclerosis 74 Sources: http://apps.who.int/medicinedocs/index/assoc/h5778e/h5778e.pdf	Palliative	Withdrawn	Elen Approved Use Indeloxazine was commonly used to treat a psychiatric symptoms, such as memory impairment or emotional disturbance associated with a cerebral infarction, hemorrhage or cerebral arteriosclerosis.

PubMed

Title	Date	PubMed
Facilitation of acetylcholine release in rat frontal cortex by indeloxazine hydrochloride: involvement of endogenous serotonin and 5-HT4 receptors.	1997 Dec	9453456
Neurochemical and behavioral characterization of potential antidepressant properties of indeloxazine hydrochloride.	1998 Sep	9833647
Functional neuroanatomy of the noradrenergic locus coeruleus: its roles in the regulation of arousal and autonomic function part II: physiological and pharmacological manipulations and pathological alterations of locus coeruleus activity in humans.	2008 Sep	19506724

Patents

Sample Use Guides

In Vivo Use Guide

20 mg three times daily

Route of Administration: Oral

In Vitro Use Guide

YM-08054-1 at concentrations of less than 1 uM considerably inhibited 5-HT uptake by synaptosomes from rat whole brain as well as noradrenaline (NA) uptake by synaptosomes from rat hippocampus. It blocks the reuptake of noradrenaline with IC50 of 3.2 uM and of serotonin with IC50 of 0.71 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:17:42 UTC 2023` Edited by `admin` on `Fri Dec 15 16:17:42 UTC 2023`
Record UNII	834M09R1KM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

INDELOXAZINE

Official Name

English

(±)-2-((INDEN-7-YLOXY)METHYL)MORPHOLINE

Systematic Name

English

MORPHOLINE, 2-((1H-INDEN-7-YLOXY)METHYL)-(±)-

Systematic Name

English

INDELOXAZINE [MI]

Common Name

English

Indeloxazine [WHO-DD]

Common Name

English

indeloxazine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265