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24524-90-1 | 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-, (2Z)-2-butenedioate (9CI)
CAS No: 24524-90-1 Catalog No: AG002OEF MDL No:
Product Description
Catalog Number:
AG002OEF
Chemical Name:
8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-, (2Z)-2-butenedioate (9CI)
CAS Number:
24524-90-1
Molecular Formula:
C20H22N2O4
Molecular Weight:
354.3997
IUPAC Name:
(Z)-but-2-enedioic acid;2-methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine
InChI:
InChI=1S/C16H18N2.C4H4O4/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18;5-3(6)1-2-4(7)8/h2-9,14H,10-11,17H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
InChI Key:
GEOCVSMCLVIOEV-BTJKTKAUSA-N
SMILES:
CN1CC(c2ccccc2)c2c(C1)c(N)ccc2.OC(=O)/C=C\C(=O)O
Properties
Complexity:
391
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1
Exact Mass:
354.158g/mol
Formal Charge:
0
Heavy Atom Count:
26
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
354.406g/mol
Monoisotopic Mass:
354.158g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
104A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Electrokinetic chromatographic estimation of the enantioselective binding of nomifensine to human serum albumin and total plasma proteins. | Biomedical chromatography : BMC 20121101 |
| Restoration of dopamine release deficits during object recognition memory acquisition attenuates cognitive impairment in a triple transgenic mice model of Alzheimer's disease. | Learning & memory (Cold Spring Harbor, N.Y.) 20120914 |
| Nomifensine alters sex differences in striatal dopaminergic function. | Synapse (New York, N.Y.) 20120801 |
| Cocaine self-administration produces pharmacodynamic tolerance: differential effects on the potency of dopamine transporter blockers, releasers, and methylphenidate. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20120601 |
| Dopamine in the hippocampus is cleared by the norepinephrine transporter. | The international journal of neuropsychopharmacology 20120501 |
| Pretreatment with nomifensine or nomifensine analogue 4-phenyl-1,2,3,4-tetrahydroisoquinoline augments methamphetamine-induced stereotypical behavior in mice. | Brain research 20120223 |
| Dopamine dysregulation in a mouse model of paroxysmal nonkinesigenic dyskinesia. | The Journal of clinical investigation 20120201 |
| Spectrofluorimetric determination of nomifensine in human plasma and urine by derivatization with fluorescamine. | Luminescence : the journal of biological and chemical luminescence 20120101 |
| SKF-83566, a D1-dopamine receptor antagonist, inhibits the dopamine transporter. | Journal of neurochemistry 20110901 |
| Inhibition of dopamine uptake by D2 antagonists: an in vivo study. | Journal of neurochemistry 20110201 |
| Long-lasting cognitive deficit induced by stress is alleviated by acute administration of antidepressants. | Psychoneuroendocrinology 20110101 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Evaluation of the effects and mechanisms of action of glufosinate, an organophosphate insecticide, on striatal dopamine release by using in vivo microdialysis in freely moving rats. | Archives of toxicology 20101001 |
| In vitro metabolism studies of nomifensine monooxygenation pathways: metabolite identification, reaction phenotyping, and bioactivation mechanism. | Drug metabolism and disposition: the biological fate of chemicals 20101001 |
| Forced swim test behavior in postpartum rats. | Pharmacology, biochemistry, and behavior 20101001 |
| Alcohol-induced depressive-like behavior is associated with cortical norepinephrine reduction. | Pharmacology, biochemistry, and behavior 20101001 |
| Dopamine uptake inhibitors but not dopamine releasers induce greater increases in motor behavior and extracellular dopamine in adolescent rats than in adult male rats. | The Journal of pharmacology and experimental therapeutics 20101001 |
| Impaired in vivo dopamine release in parkin knockout mice. | Brain research 20100917 |
| Effects of acute and sustained administration of the catecholamine reuptake inhibitor nomifensine on the firing activity of monoaminergic neurons. | Journal of psychopharmacology (Oxford, England) 20100801 |
| A rotarod test for evaluation of motor skill learning. | Journal of neuroscience methods 20100615 |
| Function of dopamine transporter is compromised in DYT1 transgenic animal model in vivo. | Journal of neurochemistry 20100401 |
| Central administration of p-hydroxyamphetamine produces a behavioral stimulant effect in rodents: evidence for the involvement of dopaminergic systems. | Psychopharmacology 20100201 |
| Identification of multiple glutathione conjugates of 8-amino- 2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline maleate (nomifensine) in liver microsomes and hepatocyte preparations: evidence of the bioactivation of nomifensine. | Drug metabolism and disposition: the biological fate of chemicals 20100101 |
| The dopamine uptake inhibitor 3 alpha-[bis(4'-fluorophenyl)metoxy]-tropane reduces cocaine-induced early-gene expression, locomotor activity, and conditioned reward. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20091101 |
| The roles of dopamine transport inhibition and dopamine release facilitation in wake enhancement and rebound hypersomnolence induced by dopaminergic agents. | Sleep 20091101 |
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| Behavioral and biochemical effects of amperozide and serotonin agents on nigrostriatal and mesolimbic dopamine systems. | The Chinese journal of physiology 20080430 |
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| Pharmacologically induced, subsecond dopamine transients in the caudate-putamen of the anesthetized rat. | Synapse (New York, N.Y.) 20070101 |
| Microelectrode array biochip: tool for in vitro drug screening based on the detection of a drug effect on dopamine release from PC12 cells. | Analytical chemistry 20060915 |
| Metabolism of nomifensine to a dihydroisoquinolinium ion metabolite by human myeloperoxidase, hemoglobin, monoamine oxidase A, and cytochrome P450 enzymes. | Drug metabolism and disposition: the biological fate of chemicals 20060801 |
| The four-plates test: anxiolytic or analgesic paradigm? | Progress in neuro-psychopharmacology & biological psychiatry 20060701 |
| Microsphere-based protease assays and screening application for lethal factor and factor Xa. | Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501 |
| Deficiency of TNF receptors suppresses microglial activation and alters the susceptibility of brain regions to MPTP-induced neurotoxicity: role of TNF-alpha. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20060401 |
| Sigma2 (sigma2) receptors as a target for cocaine action in the rat striatum. | European journal of pharmacology 20060327 |
| Changes in dopamine and acetylcholine in striatum of the awake rat after chronic treatment with a dopamine uptake blocker. | Brain research bulletin 20060215 |
| Dopamine efflux in the rat striatum evoked by electrical stimulation of the subthalamic nucleus: potential mechanism of action in Parkinson's disease. | The European journal of neuroscience 20060201 |
| Tyr-95 and Ile-172 in transmembrane segments 1 and 3 of human serotonin transporters interact to establish high affinity recognition of antidepressants. | The Journal of biological chemistry 20060127 |
| Sex differences in methamphetamine-evoked striatal dopamine of mice are reversed by nomifensine. | Neurotoxicology and teratology 20060101 |
| Neuroprotection of MPTP-induced toxicity in zebrafish dopaminergic neurons. | Brain research. Molecular brain research 20051130 |
| Dysregulation of dopamine signaling in the dorsal striatum inhibits feeding. | Brain research 20051109 |
| Voltammetric study of extracellular dopamine near microdialysis probes acutely implanted in the striatum of the anesthetized rat. | Journal of neuroscience methods 20050815 |
| Dopamine-independent locomotor actions of amphetamines in a novel acute mouse model of Parkinson disease. | PLoS biology 20050801 |
| Antidepressant-like effect of D(2/3) receptor-, but not D(4) receptor-activation in the rat forced swim test. | Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050701 |
| Comparison of the effects of nicotine and epibatidine given in combination with nomifensine on rotational behaviour in rats. | Neuroscience letters 20050624 |
| Dopamine transporters are involved in the onset of hypoxia-induced dopamine efflux in striatum as revealed by in vivo microdialysis. | Neurochemistry international 20050601 |
| The effect of nicotine in combination with various dopaminergic drugs on nigrostriatal dopamine in rats. | Naunyn-Schmiedeberg's archives of pharmacology 20050601 |
| Nicotine and epibatidine alter differently nomifensine-elevated dopamine output in the rat dorsal and ventral striatum. | European journal of pharmacology 20050328 |
| Monoamine transporter inhibitors and norepinephrine reduce dopamine-dependent iron toxicity in cells derived from the substantia nigra. | Journal of neurochemistry 20050301 |
| Dyskinesias in normal squirrel monkeys induced by nomifensine and levodopa. | Neuropharmacology 20050301 |
| Introduction of unsaturation into the N-n-alkyl chain of the nicotinic receptor antagonists, NONI and NDNI: effect on affinity and selectivity. | The AAPS journal 20050301 |
| D2 autoreceptor inhibition reveals oxygen-glucose deprivation-induced release of dopamine in guinea-pig cochlea. | Neuroscience 20050101 |
| Involvement of dopamine receptors in the anti-immobility effects of dopamine re-uptake inhibitors in the forced swimming test. | European journal of pharmacology 20041119 |
| Voltammetric study of the control of striatal dopamine release by glutamate. | Journal of neurochemistry 20041001 |
| Opioid and monoamine systems mediate the discriminative stimulus of tramadol in rats. | European journal of pharmacology 20040913 |
| Nomifensine amplifies subsecond dopamine signals in the ventral striatum of freely-moving rats. | Journal of neurochemistry 20040801 |
| Induction of gp130-related cytokines and activation of JAK2/STAT3 pathway in astrocytes precedes up-regulation of glial fibrillary acidic protein in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine model of neurodegeneration: key signaling pathway for astrogliosis in vivo? | The Journal of biological chemistry 20040507 |
| Methylphenidate restores ventral tegmental area dopamine neuron activity in prenatal ethanol-exposed rats by augmenting dopamine neurotransmission. | The Journal of pharmacology and experimental therapeutics 20040501 |
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| Differences in norepinephrine clearance in cerebellar slices from low-alcohol-sensitive and high-alcohol-sensitive rats. | Alcohol (Fayetteville, N.Y.) 20030501 |
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| Mechanism by which brain-derived neurotrophic factor increases dopamine release from the rabbit retina. | Investigative ophthalmology & visual science 20030201 |
| Aged Fischer 344 rats exhibit altered orolingual motor function: relationships with nigrostriatal neurochemical measures. | Neurobiology of aging 20030101 |
| A role for presynaptic mechanisms in the actions of nomifensine and haloperidol. | Neuroscience 20030101 |
| In vivo evidence for a lack of central effect of ebastine, an antihistaminic agent, in rats: a microdialysis study. | Japanese journal of pharmacology 20021201 |
| Aged Fischer 344 rats exhibit altered locomotion in the absence of decreased locomotor activity: exacerbation by nomifensine. | Neuroscience letters 20021129 |
| Kinetic analysis of striatal clearance of exogenous dopamine recorded by chronoamperometry in freely-moving rats. | Journal of neuroscience methods 20021115 |
| GBR-12909 effect on dopamine outflow depends on phosphorylation in the caudate nucleus of the rat. | Synapse (New York, N.Y.) 20021101 |
| Modification of the striatal dopaminergic neuron system by carbon monoxide exposure in free-moving rats, as determined by in vivo brain microdialysis. | Archives of toxicology 20021001 |
| In vivo temporal sequence of rat striatal glutamate, aspartate and dopamine efflux during apomorphine, nomifensine, NMDA and PDC in situ administration. | Neuropharmacology 20021001 |
| Bupropion inhibits nicotine-evoked [(3)H]overflow from rat striatal slices preloaded with [(3)H]dopamine and from rat hippocampal slices preloaded with [(3)H]norepinephrine. | The Journal of pharmacology and experimental therapeutics 20020901 |
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| Acute locomotor effects of fluoxetine, sertraline, and nomifensine in young versus aged Fischer 344 rats. | Pharmacology, biochemistry, and behavior 20020101 |
| Determination of release and uptake parameters from electrically evoked dopamine dynamics measured by real-time voltammetry. | Journal of neuroscience methods 20011215 |
| Modelling constant potential amperometry for investigations of dopaminergic neurotransmission kinetics in vivo. | Journal of neuroscience methods 20011215 |
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| Methyl-4-phenylpyridinium (MPP(+))-evoked dopamine release from rat striatal slices: possible roles of voltage-dependent calcium channels and reverse dopamine transport. | Neurochemistry international 20010901 |
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| A method to evaluate the diffusion rate of drugs from a microdialysis probe through brain tissue. | Journal of neuroscience methods 20010815 |
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| Vitreal dihydroxyphenylacetic acid (DOPAC) as an index of retinal dopamine release. | Journal of neurochemistry 20010301 |
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