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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H18ClNO
Molecular Weight 286.785
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SCH-23390 C-11

SMILES

[11CH3]N1CCC2=CC(Cl)=C(O)C=C2[C@H](C1)C3=CC=CC=C3

InChI

InChIKey=GOTMKOSCLKVOGG-RHHLBCDKSA-N
InChI=1S/C17H18ClNO/c1-19-8-7-13-9-16(18)17(20)10-14(13)15(11-19)12-5-3-2-4-6-12/h2-6,9-10,15,20H,7-8,11H2,1H3/t15-/m1/s1/i1-1

HIDE SMILES / InChI

Molecular Formula C17H18ClNO
Molecular Weight 286.785
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

SCH-23390 is a potent and selective antagonist of the D1A and D1B dopamine receptors having Ki of 0.2 and 0.3 nM respectively. The C11 radiolabeled version has proven to be useful as a PET imaging probe in humans for the investigation of a number of neurological conditions including Schizophrenia, Parkinson's Disease, and Huntington's Disease. It should be noted that the non-radiolabeled compound did receive preclinical interest as a potential therapeutic (annotated separately), although such efforts have been discontinued due to side-effects and a lack of therapeutic efficacy.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P21728
Gene ID: 1812.0
Gene Symbol: DRD1
Target Organism: Homo sapiens (Human)
0.2 nM [Ki]
Target ID: P21918
Gene ID: 1816.0
Gene Symbol: DRD5
Target Organism: Homo sapiens (Human)
0.3 nM [Ki]
Conditions
PubMed

PubMed

TitleDatePubMed
Preparation of 11C-labelled SCH 23390 for the in vivo study of dopamine D-1 receptors using positron emission tomography.
1986
PET analysis of human dopamine receptor subtypes using 11C-SCH 23390 and 11C-raclopride.
1987
Opposing roles of dopamine D1 and D2 receptors in nigral gamma-[3H]aminobutyric acid release?
1987 Oct
Presynaptic and postsynaptic dopaminergic binding densities in the nigrostriatal and mesocortical systems in early Parkinson's disease: a double-tracer positron emission tomography study.
1999 Nov
In vivo binding of the dopamine-1 receptor PET tracers [¹¹C]NNC112 and [¹¹C]SCH23390: a comparison study in individuals with schizophrenia.
2013 Jul
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: delivered by injection (technique not specified)
Fifteen healthy male volunteers were injected with 0.09 - 0.65 μg [11C]SCH-23390. The injections had a total radioactivity of 248 - 417 MBq and radioactivity per kg body weight of 3.16 and 4.79 MBq/kg. PET imaging data was acquired over 51 minutes in a series of consecutive thirteen minute time frames with durations of 3×60 s, 4×180 s and 6×360 s. Investigators were interested in comparing volumetric and surface-based registration and smoothing methods and found that surface-based methods yielded higher BP-ND values, lower coefficient of variation, less bias, better reliability and more precise estimates of parametric binding; therefore providing superior performance to volumetric approaches for voxelwise analysis of PET data
Route of Administration: Parenteral
In Vitro Use Guide
Curator's Comment: referenced study is for the non-radiolabeled SCH-23390
Rat brain striatal slices were preincubated with [3H]GABA and superfused in the presence of the GABA transport inhibitor nipecotic and GABA aminotransferase inhibitor aminooxyacetic acids. GABA efflux was estimated by monitoring the efflux of [3H]GABA. The overflow of GABA-evoked by electrical field stimulation was blocked by 0.5 - 10 microM of SCH 23390
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:47:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:47:33 GMT 2025
Record UNII
KJ579Y0G68
Record Status Validated (UNII)
Record Version
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Name Type Language
SCH-23390 C-11
Common Name English
11C-SCH-23390
Preferred Name English
1H-3-BENZAZEPIN-7-OL, 8-CHLORO-2,3,4,5-TETRAHYDRO-3-(METHYL-11C)-5-PHENYL-, (5R)-
Common Name English
1H-3-BENZAZEPIN-7-OL, 8-CHLORO-2,3,4,5-TETRAHYDRO-3-(METHYL-11C)-5-PHENYL-, (R)-
Common Name English
Code System Code Type Description
CAS
106647-42-1
Created by admin on Mon Mar 31 18:47:33 GMT 2025 , Edited by admin on Mon Mar 31 18:47:33 GMT 2025
PRIMARY
PUBCHEM
12928529
Created by admin on Mon Mar 31 18:47:33 GMT 2025 , Edited by admin on Mon Mar 31 18:47:33 GMT 2025
PRIMARY
FDA UNII
KJ579Y0G68
Created by admin on Mon Mar 31 18:47:33 GMT 2025 , Edited by admin on Mon Mar 31 18:47:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID90147716
Created by admin on Mon Mar 31 18:47:33 GMT 2025 , Edited by admin on Mon Mar 31 18:47:33 GMT 2025
PRIMARY
Related Record Type Details
TARGET->RADIOLIGAND
NON-LABELED -> LABELED
TARGET->RADIOLIGAND
Related Record Type Details
ACTIVE MOIETY