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 |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| D1 and D2 receptor antagonists differently affect cocaine-induced locomotor hyperactivity in the mouse. | 1991 |
|
| Evidence for an involvement of D1 and D2 dopamine receptors in mediating nicotine-induced hyperactivity in rats. | 1991 |
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| On the selection of mice for haloperidol response and non-response. | 1991 |
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| Nicotine potentiates the behavioral effects of haloperidol. | 1991 |
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| Blockade of both D-1 and D-2 dopamine receptors may induce catalepsy in mice. | 1991 |
|
| Cloning of the gene for a human dopamine D5 receptor with higher affinity for dopamine than D1. | 1991 Apr 18 |
|
| Dopamine D1 and D2 receptors mediate opposite functions in seizures induced by lithium-pilocarpine. | 1991 Mar 19 |
|
| Hypotensive and bradycardic effects elicited by spinal dopamine receptor stimulation: effects of D1 and D2 receptor agonists and antagonists. | 1991 Oct |
|
| Dopamine receptors mediate cocaine-induced temperature responses in spontaneously hypertensive and Wistar-Kyoto rats. | 1991 Sep |
|
| Morphine state-dependent learning: sensitization and interactions with dopamine receptors. | 2004 Aug 23 |
|
| A single in vivo exposure to cocaine abolishes endocannabinoid-mediated long-term depression in the nucleus accumbens. | 2004 Aug 4 |
|
| Effects of dopamine- and serotonin-related compounds on methamphetamine-induced self-injurious behavior in mice. | 2004 Dec |
|
| Effects of dopamine D1 receptor full agonists in rats trained to discriminate SKF 38393. | 2004 Feb |
|
| Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands. | 2004 Jul |
|
| Disruption of G(i/o) protein signaling in the nucleus accumbens results in a D1 dopamine receptor-mediated hyperactivity. | 2004 Sep |
|
| Dopamine receptor activation in bovine pinealocyte via a cAMP-dependent transcription pathway. | 2005 Apr |
|
| High doses of simvastatin upregulate dopamine D1 and D2 receptor expression in the rat prefrontal cortex: possible involvement of endothelial nitric oxide synthase. | 2005 Apr |
|
| Dopamine D1 and D2 receptor contributions to L-DOPA-induced dyskinesia in the dopamine-depleted rat. | 2005 Aug |
|
| Validation of the l-dopa-induced dyskinesia in the 6-OHDA model and evaluation of the effects of selective dopamine receptor agonists and antagonists. | 2005 Dec 15 |
|
| Modifications in muscarinic, dopaminergic and serotonergic receptors concentrations in the hippocampus and striatum of epileptic rats. | 2005 Dec 5 |
|
| The role of tissue plasminogen activator in methamphetamine-related reward and sensitization. | 2005 Feb |
|
| Calcineurin/NFAT-induced up-regulation of the Fas ligand/Fas death pathway is involved in methamphetamine-induced neuronal apoptosis. | 2005 Jan 18 |
|
| Dopamine uptake inhibitor-induced rotation in 6-hydroxydopamine-lesioned rats involves both D1 and D2 receptors but is modulated through 5-hydroxytryptamine and noradrenaline receptors. | 2005 Mar |
|
| Effects of intra-nucleus accumbens shell administration of dopamine agonists and antagonists on cocaine-taking and cocaine-seeking behaviors in the rat. | 2005 Nov |
|
| Induction of striatal pre- and postsynaptic damage by methamphetamine requires the dopamine receptors. | 2005 Nov |
|
| Differential activation of adenylate cyclase and receptor internalization by novel dopamine D1 receptor agonists. | 2005 Oct |
|
| Dopamine D1 or D2 receptor antagonism within the basolateral amygdala differentially alters the acquisition of cocaine-cue associations necessary for cue-induced reinstatement of cocaine-seeking. | 2006 |
|
| Histamine H3 receptor agonist- and antagonist-evoked vacuous chewing movements in 6-OHDA-lesioned rats occurs in an absence of change in microdialysate dopamine levels. | 2006 Dec 15 |
|
| The influence of central administration of dopaminergic and cholinergic agents on morphine-induced amnesia in morphine-sensitized mice. | 2006 Jan |
|
| Influence of nitric oxide on morphine-induced amnesia and interactions with dopaminergic receptor agents. | 2006 Jun 15 |
|
| Inhibition of methylphenidate-induced gene expression in the striatum by local blockade of D1 dopamine receptors: interhemispheric effects. | 2006 Jun 30 |
|
| Acute amphetamine down-regulates RGS4 mRNA and protein expression in rat forebrain: distinct roles of D1 and D2 dopamine receptors. | 2006 Mar |
|
| Acute and repeated cocaine induces alterations in FosB/DeltaFosB expression in the paraventricular nucleus of the hypothalamus. | 2006 May 23 |
|
| Delayed L-DOPA-induced hyperalgesia. | 2006 Nov |
|
| Pharmacological studies of the opioids, mood stabilizer and dopaminergic drugs on pilocarpine-induced seizures and status epilepticus. | 2006 Nov 13 |
|
| The role of peripheral and central sodium channels in mediating brain temperature fluctuations induced by intravenous cocaine. | 2006 Oct 30 |
|
| Changes in levels of D1, D2, or NMDA receptors during withdrawal from brief or extended daily access to IV cocaine. | 2007 Feb 2 |
|
| Dopaminergic and adrenergic toxicities on SK-N-MC human neuroblastoma cells are mediated through G protein signaling and oxidative stress. | 2007 Jan |
|
| Human CD4+CD25+ regulatory T cells selectively express tyrosine hydroxylase and contain endogenous catecholamines subserving an autocrine/paracrine inhibitory functional loop. | 2007 Jan 15 |
|
| Cocaine increases endoplasmic reticulum stress protein expression in striatal neurons. | 2007 Mar 16 |
|
| Spatiotemporal pattern of striatal ERK1/2 phosphorylation in a rat model of L-DOPA-induced dyskinesia and the role of dopamine D1 receptors. | 2007 Oct 1 |
|
| Effects of dopamine and NMDA receptors on cocaine-induced Fos expression in the striatum of Fischer rats. | 2008 Dec 3 |
|
| Dopamine neurotransmission is involved in the attenuating effects of 5-HT3 receptor antagonist MDL 72222 on acute methamphetamine-induced locomotor hyperactivity in mice. | 2008 Jan |
|
| Role of dopamine D1-like receptors in methamphetamine locomotor responses of D2 receptor knockout mice. | 2008 Jul |
|
| Mutual enhancement of central neurotoxicity induced by ketamine followed by methamphetamine. | 2008 Mar 1 |
|
| Transient D1 dopamine receptor expression on prefrontal cortex projection neurons: relationship to enhanced motivational salience of drug cues in adolescence. | 2008 Mar 5 |
|
| Role of dopamine D1 receptors in the prefrontal dorsal agranular insular cortex in mediating cocaine self-administration in rats. | 2008 Sep |
|
| Abstinence from chronic cocaine self-administration alters striatal dopamine systems in rhesus monkeys. | 2009 Apr |
|
| Effect of cocaine on Fas-associated protein with death domain in the rat brain: individual differences in a model of differential vulnerability to drug abuse. | 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
Sat Dec 16 05:32:00 GMT 2023
by
admin
on
Sat Dec 16 05:32:00 GMT 2023
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| Record UNII |
UGT5535REQ
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| Record Status |
Validated (UNII)
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| Record Version |
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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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