OSEMOZOTAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H21NO5
Molecular Weight	343.3737
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CNC[C@H]1COC2=CC=CC=C2O1)COC3=CC=C4OCOC4=C3

InChI

InChIKey=MEEQBDCQPIZMLY-HNNXBMFYSA-N

InChI=1S/C19H21NO5/c1-2-5-18-16(4-1)22-12-15(25-18)11-20-8-3-9-21-14-6-7-17-19(10-14)24-13-23-17/h1-2,4-7,10,15,20H,3,8-9,11-13H2/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C19H21NO5
Molecular Weight	343.3737
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.mt-pharma.co.jp/e/develop/pipeline/e_pipeline1403.pdf | https://www.ncbi.nlm.nih.gov/pubmed/8786639 | https://www.ncbi.nlm.nih.gov/pubmed/24292048

Osemozotan (also known as MKC-242) was developed as a selective 5-HT1A receptor agonist. Experiments on animal have shown that osemozotan improved most abnormal behaviors such as isolation rearing. Osemozotan was being investigated for the treatment of pain, aggressive behavior, anxiety, depression, obsessive-compulsive disorder, and drug dependence with methamphetamine and cocaine. However, all these studies were suspended. In the USA osemozotan participated in phase II clinical trial for the insomnia patients, however, the study was terminated because of the license agreement.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8786639	Agonist 2752		0.35 nM [Ki]

PubMed

Title	Date	PubMed
Modification of cocaine-induced behavioral and neurochemical effects by serotonin1A receptor agonist/antagonist in mice.	2006-12-01	16952156
Inhibitory action of 5-HT1A agonist MKC-242 on triazolam-induced phase advances in hamster circadian activity rhythms.	2005-05	15879674
The 5-HT1A receptor agonist MKC-242 reverses isolation rearing-induced deficits of prepulse inhibition in mice.	2003-10	12768276
The 5-HT1A receptor agonist MKC-242 increases the exploratory activity of mice in the elevated plus-maze.	2003-01-01	12498918
Selective reduction by isolation rearing of 5-HT1A receptor-mediated dopamine release in vivo in the frontal cortex of mice.	2002-10	12423245
Modulation by 5-hT2A receptors of aggressive behavior in isolated mice.	2002-05	12083749
Involvement of benzodiazepine binding sites in an antiaggressive effect by 5-HT(1A) receptor activation in isolated mice.	2001-12-07	11740952
Functional alteration of brain dopaminergic system in isolated aggressive mice.	2001-09	11769459

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:24:46 GMT 2025` Edited by `admin` on `Mon Mar 31 18:24:46 GMT 2025`
Record UNII	M65825806Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MN-305

Preferred Name

English

OSEMOZOTAN

Official Name

English

osemozotan [INN]

Common Name

English

3-(1,3-BENZODIOXOL-5-YLOXY)-N-(((2S)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL)METHYL)PROPAN-1-AMINE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C47794