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Details

Stereochemistry ACHIRAL
Molecular Formula C18H20N6.2C4H4O4
Molecular Weight 552.5359
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of 2-PHENYL-5-(4-((2-PYRIMIDINYL)-PIPERAZIN-1-YL)-METHYL)-IMIDAZOLE DIMALEATE

SMILES

OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.C(N1CCN(CC1)C2=NC=CC=N2)C3=CN=C(N3)C4=CC=CC=C4

InChI

InChIKey=CEFBXMNJODPQHJ-SPIKMXEPSA-N
InChI=1S/C18H20N6.2C4H4O4/c1-2-5-15(6-3-1)17-21-13-16(22-17)14-23-9-11-24(12-10-23)18-19-7-4-8-20-18;2*5-3(6)1-2-4(7)8/h1-8,13H,9-12,14H2,(H,21,22);2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C18H20N6
Molecular Weight 320.3916
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

NGD 94-1 is high affinity D4 receptor ligand, shows selective over D1, D2, D3 and D5 receptors. Displays antagonist activity at the human D4.2 receptor (Ki = 3.6 nM in transfected CHO cells) and exhibits agonist activity at the D4.4 receptor in HEK 293 cells.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.8 nM [Ki]
PubMed

PubMed

TitleDatePubMed
I. NGD 94-1: identification of a novel, high-affinity antagonist at the human dopamine D4 receptor.
1997 Aug
2-Phenyl-4(5)-[[4-(pyrimidin-2-yl)piperazin-1-yl]methyl]imidazole. A highly selective antagonist at cloned human D4 receptors.
1997 Jan 3
Patents

Patents

Sample Use Guides

In Vivo Use Guide
In drug reversal studies NGD94-1 was administered at 1 or 5 mg/kg intramuscularly 45 min prior to testing. Haloperidol was given at 0.025 mg/kg intramuscularly 30 min prior to testing
Route of Administration: Intramuscular
In Vitro Use Guide
The dopamine D4 receptor is a Gprotein-coupled receptor and is negatively linked to adenylate cyclase, so that agonists at D4 receptors will inhibit forskolin-stimulated cAMP production. CHO cells stably expressing the cloned human D4.2 receptor were plated in 24-well plates 1 to 2 days before the assay, and were grown to confluence in Ham’s media with 10% FBS. On the day of the assay, each well was washed three times with serum-free Ham’s media containing 0.1 M HEPES. After a 30-min preincubation with NGD 94-1 and 50 mkM IBMX (phosphodiesterase inhibitor) at 37°C, cells were incubated with 5 mM forskolin for 15 min at 37°C. To stop the reaction, the plates were washed three times with cold PBS. Each well was incubated with 0.1 mM HCl for 20 min at room temperature. An aliquot of each sample was transferred to 12 * 75 mm polypropylene tubes, and the acid was neutralized with the addition of a solution containing 0.1 mM HEPES-0.1 mM K2CO3. The remaining acid was removed from the plates, and the cells were lysed with 0.5% Triton X-100. The protein content of each well was then determined with the Bio-Rad protein assay (Hercules, CA). The cAMP content in the neutralized extracts was determined with a cAMP RIA kit (NEN-DuPont, Boston, MA). The samples were quantitated using a gamma counter with an efficiency of 80 to 85%
Substance Class Chemical
Created
by admin
on Tue Oct 22 15:47:18 UTC 2019
Edited
by admin
on Tue Oct 22 15:47:18 UTC 2019
Record UNII
7E1IX9C8PJ
Record Status Validated (UNII)
Record Version
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Name Type Language
2-PHENYL-5-(4-((2-PYRIMIDINYL)-PIPERAZIN-1-YL)-METHYL)-IMIDAZOLE DIMALEATE
Common Name English
PYRIMIDINE, 2-(4-((2-PHENYL-1H-IMIDAZOL-4-YL)METHYL)-1-PIPERAZINYL)-, (2Z)-2-BUTENEDIOATE (1:2)
Systematic Name English
CPDD-0045
Code English
NGD-94-1
Code English
NGD-941
Code English
Code System Code Type Description
CAS
179333-18-7
Created by admin on Tue Oct 22 15:47:18 UTC 2019 , Edited by admin on Tue Oct 22 15:47:18 UTC 2019
PRIMARY
PUBCHEM
188942
Created by admin on Tue Oct 22 15:47:18 UTC 2019 , Edited by admin on Tue Oct 22 15:47:18 UTC 2019
PRIMARY
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