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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H21NO5.ClH
Molecular Weight 379.835
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OSEMOZOTAN HYDROCHLORIDE

SMILES

Cl.C(CNC[C@H]1COC2=CC=CC=C2O1)COC3=CC4=C(OCO4)C=C3

InChI

InChIKey=GGNCUSDIUUCNKE-RSAXXLAASA-N
InChI=1S/C19H21NO5.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.35 nM [Ki]
PubMed

PubMed

TitleDatePubMed
Modification of cocaine-induced behavioral and neurochemical effects by serotonin1A receptor agonist/antagonist in mice.
2006-12-01
Inhibitory action of 5-HT1A agonist MKC-242 on triazolam-induced phase advances in hamster circadian activity rhythms.
2005-05
The 5-HT1A receptor agonist MKC-242 reverses isolation rearing-induced deficits of prepulse inhibition in mice.
2003-10
The 5-HT1A receptor agonist MKC-242 increases the exploratory activity of mice in the elevated plus-maze.
2003-01-01
Selective reduction by isolation rearing of 5-HT1A receptor-mediated dopamine release in vivo in the frontal cortex of mice.
2002-10
Modulation by 5-hT2A receptors of aggressive behavior in isolated mice.
2002-05
Involvement of benzodiazepine binding sites in an antiaggressive effect by 5-HT(1A) receptor activation in isolated mice.
2001-12-07
Functional alteration of brain dopaminergic system in isolated aggressive mice.
2001-09
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:32:23 GMT 2025
Edited
by admin
on Mon Mar 31 18:32:23 GMT 2025
Record UNII
F0WKFYPQL8
Record Status Validated (UNII)
Record Version
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Name Type Language
MKC-242
Preferred Name English
OSEMOZOTAN HYDROCHLORIDE
Systematic Name English
1,4-BENZODIOXIN-2-METHANAMINE, N-(3-(1,3-BENZODIOXOL-5-YLOXY)PROPYL)-2,3-DIHYDRO-, HYDROCHLORIDE (1:1), (2S)-
Systematic Name English
5-(3-((1,4-BENZODIOXAN-2-YLMETHYL)AMINO)PROPOXY)-1,3-BENZODIOXOLE HYDROCHLORIDE, S-
Systematic Name English
Code System Code Type Description
EPA CompTox
DTXSID00929762
Created by admin on Mon Mar 31 18:32:23 GMT 2025 , Edited by admin on Mon Mar 31 18:32:23 GMT 2025
PRIMARY
PUBCHEM
198746
Created by admin on Mon Mar 31 18:32:23 GMT 2025 , Edited by admin on Mon Mar 31 18:32:23 GMT 2025
PRIMARY
CAS
137275-80-0
Created by admin on Mon Mar 31 18:32:23 GMT 2025 , Edited by admin on Mon Mar 31 18:32:23 GMT 2025
PRIMARY
FDA UNII
F0WKFYPQL8
Created by admin on Mon Mar 31 18:32:23 GMT 2025 , Edited by admin on Mon Mar 31 18:32:23 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE