Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H18ClNO |
| Molecular Weight | 287.784 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCC2=CC(Cl)=C(O)C=C2[C@H](C1)C3=CC=CC=C3
InChI
InChIKey=GOTMKOSCLKVOGG-OAHLLOKOSA-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
| Molecular Formula | C17H18ClNO |
| Molecular Weight | 287.784 |
| 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 dopamine-1 and dopamine-5 receptors (Ki = 0.2 and 0.3 nM respectively). It was found to prevent death from d-amphetamine overdose in rats and has also been investigated as a potential treatment for Parkinson's Disease and Bipolar Disorder. A single clinical trial was conducted in healthy humans where SCH-23390 induced akathisia (motor restlessness). Preclinical and clinical trials as therapeutic have been discontinued due to side-effects and lack of efficacy. However, it should be noted that a C11 radiolabeled version of the compound has been synthesized and used as a PET imaging probe for the study of Parkinson's Disease and Huntington's Disease.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Blockade of both D-1 and D-2 dopamine receptors may induce catalepsy in mice. | 1991 |
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| RGS mRNA expression in rat striatum: modulation by dopamine receptors and effects of repeated amphetamine administration. | 1999 Apr |
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| Dopaminergic neurotransmission at the paraventricular nucleus of hypothalamus in central regulation of penile erection in the rat. | 1999 Jul |
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| Macrophage Fcgamma receptors expression is altered by treatment with dopaminergic drugs. | 1999 Mar |
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| Estrogen priming modulates autoreceptor-mediated potentiation of dopamine uptake. | 2000 Aug 11 |
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| Activation of an effector immediate-early gene arc by methamphetamine. | 2000 Sep |
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| Blockade of D1 dopamine receptors in the ventral tegmental area decreases cocaine reward: possible role for dendritically released dopamine. | 2001 Aug 1 |
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| Cocaine-predictive stimulus induces drug-seeking behavior and neural activation in limbic brain regions after multiple months of abstinence: reversal by D(1) antagonists. | 2001 Feb 13 |
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| Involvement of serotonergic and dopaminergic mechanisms in hyperthermia induced by a serotonin-releasing drug, p-chloroamphetamine in mice. | 2001 Nov 2 |
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| Hypothalamic CRH mRNA levels are differentially modulated by repeated 'binge' cocaine with or without D(1) dopamine receptor blockade. | 2001 Oct 19 |
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| Neuropharmacological profile of a novel potential atypical antipsychotic drug Y-931 (8-fluoro-12-(4-methylpiperazin-1-yl)- 6H-[1]benzothieno[2,3-b][1,5] benzodiazepine maleate). | 2002 Apr |
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| Characterization of the distribution of the cocaine priming threshold and the effect of SCH23390. | 2002 Aug 16 |
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| Impaired D2 dopamine receptor function in mice lacking type 5 adenylyl cyclase. | 2002 Sep 15 |
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| Prenatal and neonatal exposure to bisphenol-A enhances the central dopamine D1 receptor-mediated action in mice: enhancement of the methamphetamine-induced abuse state. | 2003 |
|
| Excitation by dopamine of rat subthalamic nucleus neurones in vitro-a direct action with unconventional pharmacology. | 2003 |
|
| Potentiation of domperidone-induced catalepsy by a P-glycoprotein inhibitor, cyclosporin A. | 2003 Apr |
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| Dopamine receptor activation in bovine pinealocyte via a cAMP-dependent transcription pathway. | 2005 Apr |
|
| Dopamine D1 and D2 receptor contributions to L-DOPA-induced dyskinesia in the dopamine-depleted rat. | 2005 Aug |
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| Effects of intra-nucleus accumbens shell administration of dopamine agonists and antagonists on cocaine-taking and cocaine-seeking behaviors in the rat. | 2005 Nov |
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| Induction of striatal pre- and postsynaptic damage by methamphetamine requires the dopamine receptors. | 2005 Nov |
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| Differential activation of adenylate cyclase and receptor internalization by novel dopamine D1 receptor agonists. | 2005 Oct |
|
| Influence of nitric oxide on morphine-induced amnesia and interactions with dopaminergic receptor agents. | 2006 Jun 15 |
|
| Acute and repeated cocaine induces alterations in FosB/DeltaFosB expression in the paraventricular nucleus of the hypothalamus. | 2006 May 23 |
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| Effects of dopamine and NMDA receptors on cocaine-induced Fos expression in the striatum of Fischer rats. | 2008 Dec 3 |
|
| Abstinence from chronic cocaine self-administration alters striatal dopamine systems in rhesus monkeys. | 2009 Apr |
|
| Combined scopolamine and ethanol treatment results in a locomotor stimulant response suggestive of synergism that is not blocked by dopamine receptor antagonists. | 2009 Mar |
Sample Use Guides
SCH-23390 was tested in four healthy subjects at doses of 310–810 micrograms delivered intravenously. SCH-23390 induced akathisia at the three highest doses.
Route of Administration:
Intravenous
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
Edited
Mon Mar 31 21:30:20 GMT 2025
by
admin
on
Mon Mar 31 21:30:20 GMT 2025
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| Record UNII |
UGT5535REQ
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| Record Status |
Validated (UNII)
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C534628
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SCH 23390
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UGT5535REQ
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DTXSID40873376
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87075-17-0
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3036864
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admin on Mon Mar 31 21:30:20 GMT 2025 , Edited by admin on Mon Mar 31 21:30:20 GMT 2025
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| Related Record | Type | Details | ||
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OFF-TARGET->INHIBITOR |
Ki
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TARGET -> INHIBITOR |
BINDING
Ki
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OFF-TARGET->INHIBITOR |
BINDING
Ki
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OFF-TARGET->INHIBITOR |
Ki
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TARGET -> INHIBITOR |
Ki
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SALT/SOLVATE -> PARENT |
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LABELED -> NON-LABELED |
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SALT/SOLVATE -> PARENT |
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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