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Details

Stereochemistry ACHIRAL
Molecular Formula C21H14ClNO3
Molecular Weight 363.794
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of L-701324

SMILES

OC1=C(C(=O)NC2=C1C=CC(Cl)=C2)C3=CC(OC4=CC=CC=C4)=CC=C3

InChI

InChIKey=FLVRDMUHUXVRET-UHFFFAOYSA-N
InChI=1S/C21H14ClNO3/c22-14-9-10-17-18(12-14)23-21(25)19(20(17)24)13-5-4-8-16(11-13)26-15-6-2-1-3-7-15/h1-12H,(H2,23,24,25)

HIDE SMILES / InChI

Molecular Formula C21H14ClNO3
Molecular Weight 363.794
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

L-701,324 [7-chloro-4-hydroxy-3(3-phenoxy) phenylquinoline-2-(H)-one] is a selective and full antagonist at the glycine site of the NMDA receptor, has been studied on animals as potential antipsychotic and anticonvulsant agent. But these studies were discontinued.

Originator

Curator's Comment: # Merck Sharp and Dohme Research Laboratories

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cannabinoid-induced increase in relapse-like drinking is prevented by the blockade of the glycine-binding site of N-methyl-D-aspartate receptors.
2009-01-23
Ionotropic and metabotropic glutamate receptor antagonism attenuates cue-induced cocaine seeking.
2006-04
NMDA antagonists inhibit the development of ethanol dependence in rats.
2002-01-12
L-701,324, a selective antagonist at the glycine site of the NMDA receptor, counteracts haloperidol-induced muscle rigidity in rats.
1999-04
The role of striatal glutamate receptors in models of Parkinson's disease.
1998
The atypical neuroleptic profile of the glycine/N-methyl-D-aspartate receptor antagonist, L-701,324, in rodents.
1996-05
3'-(Arylmethyl)- and 3'-(aryloxy)-3-phenyl-4-hydroxyquinolin-2(1H)-ones: orally active antagonists of the glycine site on the NMDA receptor.
1994-05-13

Sample Use Guides

in mice: At 5 and 10 mg kg-', L-701,324 virtually abolished the propagation of SD and the drug was effective within 30 min after administration and for up to 2.5 h. These doses are around 5-10 fold the ED50 for inhibition of audiogenic seizures in the DBA/2 mouse, a model extremely sensitive to NMDA-receptor blockade. In contrast, 10 mg kg-' L-701,324 inhibited K+ elicitation by around 50% only. Pretreatment with L-701,324 dose-dependently antagonized amphetamine-induced hyperactivity in the mouse (ED50 = 1.12 +/- 0.45 mg/kg p.o.), an effect which was similar to that of the classical neuroleptic, haloperidol, and the atypical neuroleptic, clozapine. In addition, p.o. administration of L-701,324 (2.5 or 5 mg/kg) attenuated the hyperactivity response induced by amphetamine infusion into the rat nucleus accumbens. In contrast to haloperidol, however, stereotyped sniffing and licking/biting, induced by either the systemic administration of apomorphine or infusion of amphetamine into the striatum, was not altered in rats pretreated with L-701,324 (30 or 100 mg/kg p.o.).
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 22:11:54 GMT 2025
Edited
by admin
on Mon Mar 31 22:11:54 GMT 2025
Record UNII
I9WY146163
Record Status Validated (UNII)
Record Version
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Name Type Language
L-701,324
Preferred Name English
L-701324
Common Name English
2(1H)-QUINOLINONE, 7-CHLORO-4-HYDROXY-3-(3-PHENOXYPHENYL)-
Systematic Name English
Code System Code Type Description
FDA UNII
I9WY146163
Created by admin on Mon Mar 31 22:11:54 GMT 2025 , Edited by admin on Mon Mar 31 22:11:54 GMT 2025
PRIMARY
PUBCHEM
54682505
Created by admin on Mon Mar 31 22:11:54 GMT 2025 , Edited by admin on Mon Mar 31 22:11:54 GMT 2025
PRIMARY
EPA CompTox
DTXSID00162016
Created by admin on Mon Mar 31 22:11:54 GMT 2025 , Edited by admin on Mon Mar 31 22:11:54 GMT 2025
PRIMARY
CAS
142326-59-8
Created by admin on Mon Mar 31 22:11:54 GMT 2025 , Edited by admin on Mon Mar 31 22:11:54 GMT 2025
PRIMARY
Related Record Type Details
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