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14173-39-8

14173-39-8 | L-Phenylalanine, 4-chloro-

CAS No: 14173-39-8 Catalog No: AG001GY2 MDL No:MFCD00063065

Product Description

Catalog Number:
AG001GY2
Chemical Name:
L-Phenylalanine, 4-chloro-
CAS Number:
14173-39-8
Molecular Formula:
C9H10ClNO2
Molecular Weight:
199.6342
MDL Number:
MFCD00063065
IUPAC Name:
(2S)-2-amino-3-(4-chlorophenyl)propanoic acid
InChI:
InChI=1S/C9H10ClNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)/t8-/m0/s1
InChI Key:
NIGWMJHCCYYCSF-QMMMGPOBSA-N
SMILES:
N[C@H](C(=O)O)Cc1ccc(cc1)Cl
UNII:
SNM151OE2C

Properties

Complexity:
179  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
199.04g/mol
Formal Charge:
0
Heavy Atom Count:
13  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
199.634g/mol
Monoisotopic Mass:
199.04g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
63.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.5  

Literature

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Antidepressants in the treatment of fibromyalgia. Neuropsychiatric disease and treatment 20061201
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Potentiating effects of L-type Ca(2+) channel blockers on pentobarbital-induced hypnosis are influenced by serotonergic system. Journal of neural transmission (Vienna, Austria : 1996) 20061001
Serotonergic modulation of male-like pseudocopulatory behavior in the parthenogenetic whiptail lizard, Cnemidophorus uniparens. Hormones and behavior 20060901
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Hormones in the nucleus. Immunologically demonstrable biogenic amines (serotonin, histamine) in the nucleus of rat peritoneal mast cells. Life sciences 20060313
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Serotonin depletion, cortical spreading depression, and trigeminal nociception. Headache 20060101
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Effects of central and peripheral depletion of serotonergic system on carrageenan-induced paw oedema. International immunopharmacology 20051101
Harmane inhibits serotonergic dorsal raphe neurons in the rat. Psychopharmacology 20051101
Neighbouring group processes in the deamination of protonated phenylalanine derivatives. Organic & biomolecular chemistry 20051021
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Serotonergic influence on the potentiation of D-amphetamine and apomorphine-induced rotational behavior by the alpha2-adrenoceptor antagonist 2-methoxy idazoxan in hemiparkinsonian rats. Journal of neural transmission (Vienna, Austria : 1996) 20050901
Electroacupuncture prevents cognitive deficits in pilocarpine-epileptic rats. Neuroscience letters 20050826
Effect of 5-HT depletion on cardiovascular vagal reflex sensitivity in awake and anesthetized rats. Brain research 20050823
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Serotonin 5-HT receptor blockade enhances Ca(2+)/calmodulin-dependent protein kinase II function and membrane expression of AMPA receptor subunits in the rat hippocampus: implications for memory formation. Journal of neurochemistry 20050801
Involvement of central serotonergic systems in dextromethorphan-induced behavioural syndrome in rats. Indian journal of experimental biology 20050701
The role of 5-HT in the impairment of thermoregulation observed in rats administered MDMA ('ecstasy') when housed at high ambient temperature. Psychopharmacology 20050601
Antidepressant-like effect of the selective 5-HT1B receptor agonist CP 94253: a possible mechanism of action. European journal of pharmacology 20050523
Reduced serotonin synthesis during early embryogeny changes effect of subsequent prenatal stress on persistent pain in the formalin test in adult male and female rats. Brain research 20050503
Exacerbation of harmaline-induced tremor by imipramine. Pharmacology, biochemistry, and behavior 20050501
Effects of serotonin and serotonergic agonists and antagonists on the production of tumor necrosis factor alpha and interleukin-6. Psychiatry research 20050430
Involvement of serotonin in the hypoglycemic response to 2 Hz electroacupuncture of zusanli acupoint (ST36) in rats. Neuroscience letters 20050429
Postsynaptic 5-HT1B receptors modulate electroshock-induced generalised seizures in rats. British journal of pharmacology 20050301
A reassessment of the role of serotonergic system in the control of feeding behavior. Anais da Academia Brasileira de Ciencias 20050301
Strategy for chromosomal gene targeting in RecA-deficient Escherichia coli strains. BioTechniques 20050301
Serotonin refines the locomotor-related alternations in the in vitro neonatal rat spinal cord. The European journal of neuroscience 20050301
Long-lasting effects of serotonin deficiency on differentiating peptidergic neurons in the rat suprachiasmatic nucleus. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20050201
GABAB receptor antagonist-mediated antidepressant-like behavior is serotonin-dependent. The Journal of pharmacology and experimental therapeutics 20050101
Up-regulation of P-glycoprotein expression in small intestine under chronic serotonin-depleted conditions in rats. The Journal of pharmacology and experimental therapeutics 20050101
Characterization of antinociceptive activity of novel endomorphin-2 and morphiceptin analogs modified in the third position. Biochemical pharmacology 20050101
[Astroglia formation in the neocortex of mice after temporary prenatal serotonin depletion]. Morfologiia (Saint Petersburg, Russia) 20050101
The role of 5-HT1A receptors in the proliferation and survival of progenitor cells in the dentate gyrus of the adult hippocampus and their regulation by corticoids. Neuroscience 20050101
Tetrandrine, a bisbenzylisoquinoline alkaloid from Chinese herb Radix, augmented the hypnotic effect of pentobarbital through serotonergic system. European journal of pharmacology 20041215
Elevated serotonin is involved in hyperactivity but not in the paradoxical effect of amphetamine in mice neonatally lesioned with 6-hydroxydopamine. Journal of neuroscience research 20041015
5-HT-mediated inhibition of cardiovagal baroreceptor reflex response during defense reaction in the rat. American journal of physiology. Heart and circulatory physiology 20041001
Effects of autacoid inhibitors and of an antagonist on malaria infection in mice. Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20040801
Immediate plasticity in the motor pathways after spinal cord hemisection: implications for transcranial magnetic motor-evoked potentials. Experimental neurology 20040601
NMDA receptor subunit and CaMKII changes in rat hippocampus induced by acute MDMA treatment: a mechanism for learning impairment. Psychopharmacology 20040501
ADAM is an effective tool for in vivo study of serotonergic function: validation in rat models. Synapse (New York, N.Y.) 20040501
Stimulation of the immune response during activation of the dopaminergic system in mice with opposite types of behavior. Neuroscience and behavioral physiology 20040501
5-HT has contrasting effects in the frontal cortex, but not the hypothalamus, on changes in noradrenaline efflux induced by the monoamine releasing-agent, d-amphetamine, and the reuptake inhibitor, BTS 54 354. Neuropharmacology 20040301
Brain serotonin depletion enhances the sodium appetite induced by sodium depletion or beta-adrenergic stimulation. Anais da Academia Brasileira de Ciencias 20040301
The central serotonergic system mediates the analgesic effect of electroacupuncture on ZUSANLI (ST36) acupoints. Journal of biomedical science 20040101
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L. Acta biologica Hungarica 20040101
5-HT1A and beta-adrenergic receptors regulate proliferation of rat blood lymphocytes. Neuroimmunomodulation 20040101
Depletion and restoration of endogenous monoamines affects beta-CIT binding to serotonin but not dopamine transporters in non-human primates. Journal of neural transmission. Supplementum 20040101
Emetic action of the prostanoid TP receptor agonist, U46619, in Suncus murinus (house musk shrew). European journal of pharmacology 20031215
Effects of fenfluramine and antidepressants on protein kinase C activity in rat cortical synaptoneurosomes. Synapse (New York, N.Y.) 20031201
Expression of tryptophan 5-hydroxylase gene during sea urchin neurogenesis and role of serotonergic nervous system in larval behavior. The Journal of comparative neurology 20031110
Serotonin synthesis inhibition in olivo-cerebellar system attenuates harmaline-induced tremor in Swiss albino mice. Behavioural brain research 20031017
Elimination of serotonergic cells induces a marked increase in generation of dopaminergic neurons from mesencephalic precursors. The European journal of neuroscience 20031001
Role of serotonergic mechanisms in leptin-induced suppression of milk intake in mice. Neuroscience letters 20030918
The effects of serotonin on the differentiation of neurons producing vasoactive intestinal polypeptide in the suprachiasmatic nucleus of the rat. Neuroscience and behavioral physiology 20030901
Effect of the inhibition of serotonin biosynthesis on the antinociception induced by nonsteroidal anti-inflammatory drugs. Brain research bulletin 20030830
Characterization of tryptophan high affinity transport system in pinealocytes of the rat. Day-night modulation. Amino acids 20030701
m-CPP-induced self-grooming is mediated by 5-HT2C receptors. Behavioural brain research 20030616
Influence of serotonin on the development and migration of gonadotropin-releasing hormone neurones in rat foetuses. Journal of neuroendocrinology 20030601
Use of Arc expression as a molecular marker of increased postsynaptic 5-HT function after SSRI/5-HT1A receptor antagonist co-administration. Journal of neurochemistry 20030601
Serotonergic mediation of the antidepressant-like effects of nitric oxide synthase inhibitors. Neuropharmacology 20030401
Increases in avoidance responding produced by REM sleep deprivation or serotonin depletion are reversed by administration of 5-hydroxytryptophan. Behavioural brain research 20030318
Serotonin-GABA interactions in the modulation of mu- and kappa-opioid analgesia. Neuropharmacology 20030301
Serotonin depletion increases respiratory variability in freely moving rats: implications for panic disorder. The international journal of neuropsychopharmacology 20030301
Host brain regulation of dopaminergic grafts function: role of the serotonergic and noradrenergic systems in amphetamine-induced responses. Synapse (New York, N.Y.) 20030101
Lack of effects by tricyclic antidepressant and serotonin inhibitors on anorexia in MCG 101 tumor-bearing mice with eicosanoid-related cachexia. Nutrition (Burbank, Los Angeles County, Calif.) 20030101
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways]. Eksperimental'naia i klinicheskaia farmakologiia 20030101
Decreased serotonin level during pregnancy alters morphological and functional characteristics of tonic nociceptive system in juvenile offspring of the rat. Reproductive biology and endocrinology : RB&E 20030101
Neural stem cells and the regulation of adult neurogenesis. Reproductive biology and endocrinology : RB&E 20030101
Depletion of endogenous serotonin synthesis with p-CPA attenuates upregulation of constitutive isoform of heme oxygenase-2 expression, edema formation and cell injury following a focal trauma to the rat spinal cord. Acta neurochirurgica. Supplement 20030101
Pharmacological blockage of serotonin biosynthesis and circadian changes in oxaliplatin toxicity in rats. Chronobiology international 20021101
[Activation of dopaminergic system stimulates an immune response in mice with opposite type of behaviour]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20021101
MDMA- and p-chlorophenylalanine-induced reduction in 5-HT concentrations: effects on serotonin transporter densities. European journal of pharmacology 20021025
FR143166 attenuates spinal pain transmission through activation of the serotonergic system. European journal of pharmacology 20021011
Neither increased nor decreased availability of cortical serotonin (5HT) disturbs barrel field formation in isocaloric undernourished rat pups. International journal of developmental neuroscience : the official journal of the International Society for Developmental Neuroscience 20021001
The spinal antinociceptive effect of kyotorphin in mice: involvement of the descending noradrenergic and serotonergic systems. Neuroscience letters 20020830
Postsynaptic 5-HT(1A) receptors mediate an increase in locomotor activity in the monoamine-depleted rat. Psychopharmacology 20020801
Modulation of serotonergic projection from dorsal raphe nucleus to basolateral amygdala on sleep-waking cycle of rats. Brain research 20020726
Decreased marble burying behavior in female mice lacking neuromedin-B receptor (NMB-R) implies the involvement of NMB/NMB-R in 5-HT neuron function. Brain research 20020628
Postural modifications and neuronal excitability changes induced by a short-term serotonin depletion during neonatal development in the rat. The Journal of neuroscience : the official journal of the Society for Neuroscience 20020615
The inhibition of tryptophan hydroxylase, not protein synthesis, reduces the brain trapping of alpha-methyl-L-tryptophan: an autoradiographic study. Neurochemistry international 20020601
Effect of NMDA antagonists, an NMDA agonist, and serotonin depletion on acute tolerance to ethanol. Pharmacology, biochemistry, and behavior 20020501
Modulation of 5-HT4 receptor function in the rat isolated ileum by fluoxetine: the involvement of endogenous 5-hydroxytryptamine. British journal of pharmacology 20020501
Effect of rofecoxib on nociception and the serotonin system in the rat brain. Inflammation research : official journal of the European Histamine Research Society ... [et al.] 20020301
Involvement of monoaminergic system in the antidepressant-like effect of the hydroalcoholic extract of Siphocampylus verticillatus. Life sciences 20020208
Effects of pharmacological agents upon a transgenic model of Parkinson's disease in Drosophila melanogaster. The Journal of pharmacology and experimental therapeutics 20020101
Counteraction of the rapid tolerance to 8-hydroxy-2-(di-n-propylamino)tetralin-induced hypothermia in rats by activation of the GABAA receptor-chloride channel complex. Pharmacology & toxicology 20020101
Assessment of spinal cord pathology following trauma using early changes in the spinal cord evoked potentials: a pharmacological and morphological study in the rat. Muscle & nerve. Supplement 20020101
[Behavioral effects of L-tryptophan and p-chlorophenylalanine after adrenalectomy or dexamethasone administration in rats]. Zhurnal vysshei nervnoi deiatelnosti imeni I P Pavlova 20020101
Self-biting induced by activation of L-type calcium channels in mice: serotonergic influences. Developmental neuroscience 20020101
Control of dorsal raphe serotonergic neurons by the medial prefrontal cortex: Involvement of serotonin-1A, GABA(A), and glutamate receptors. The Journal of neuroscience : the official journal of the Society for Neuroscience 20011215
Plasma glucose-lowering effect of tramadol in streptozotocin-induced diabetic rats. Diabetes 20011201
Reversible inhibition of cathepsin L-like proteases by 4-mer pseudopeptides. FEBS letters 20011102
Effects of endogenous neurotransmitters on the in vivo binding of dopamine and 5-HT radiotracers in mice. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20011101
Estradiol and para-chlorophenylalanine downregulate the expression of brain aromatase and estrogen receptor-alpha mRNA during the critical period of feminization in tilapia (Oreochromis mossambicus). Neuroendocrinology 20011101
Serotonin mediates oestrogen stimulation of cell proliferation in the adult dentate gyrus. The European journal of neuroscience 20011101
p-Chlorophenylalanine eliminates long-term modulation of the exercise ventilatory response in goats. Respiration physiology 20011101
Altered responsiveness to 5-HT at the crayfish neuromuscular junction due to chronic p-CPA and m-CPP treatment. Brain research 20011019
Effects of serotonin synthesis blockade on interleukin-1 beta action in the brain of rats. Brain research 20011012
Serotonin depletion attenuates cocaine seeking but enhances sucrose seeking and the effects of cocaine priming on reinstatement of cocaine seeking in rats. Psychopharmacology 20011001
[Tyrosine hydroxylase expression in differentiating neurons of the rat arcuate nucleus: inhibitory effect of serotoninergic afferents]. Rossiiskii fiziologicheskii zhurnal imeni I.M. Sechenova 20011001
The spinal antinociceptive effect of FR140423 in mice involvement of the descending noradrenergic and serotonergic systems. Life sciences 20010928
Antidepressant-like behavioral effects in 5-hydroxytryptamine(1A) and 5-hydroxytryptamine(1B) receptor mutant mice. The Journal of pharmacology and experimental therapeutics 20010901
In vivo resetting of the hamster circadian clock by 5-HT7 receptors in the suprachiasmatic nucleus. The Journal of neuroscience : the official journal of the Society for Neuroscience 20010715
Effect of serotonin depletion by p-chlorophenylalanine on serum prolactin levels in estrogen-treated ovariectomized rats: insights concerning the serotoninergic, dopaminergic and opioid systems. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20010601
Investigations on possible serotonergic involvement in effects of OB-200G (polyherbal preparation) on food intake in female mice. European journal of nutrition 20010601
Methylenedioxymethamphetamine-induced suppression of interleukin-1beta and tumour necrosis factor-alpha is not mediated by serotonin. European journal of pharmacology 20010420
Reduced brain serotonin activity disrupts prepulse inhibition of the acoustic startle reflex. Effects of 5,7-dihydroxytryptamine and p-chlorophenylalanine. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20010401
Pharmacological studies on the monoaminergic influence on the synthesis and expression of neuropeptide Y and corticotropin releasing factor in rat brain amygdala. Neuropeptides 20010401
Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats. Pharmacology, biochemistry, and behavior 20010401
Disruption of neuroendocrine control of luteinizing hormone secretion by aroclor 1254 involves inhibition of hypothalamic tryptophan hydroxylase activity. Biology of reproduction 20010301
Apomorphine-induced aggressive behaviour in para-chlorophenylalanine-treated male rats: implications to brain. Pharmacology & toxicology 20010301
Effects of p-chlorophenylalanine on striatal acetylcholinesterase activity and on biogenic amine levels in nuclei raphe and caudate-putamen during physostigmine-induced tremor in rats. Neuroscience letters 20010216
Intestinal serotonin acts as a paracrine substance to mediate vagal signal transmission evoked by luminal factors in the rat. The Journal of physiology 20010201
Behavioral effects of para-chlorophenylalanine in gonadectomized male rats. Bulletin of experimental biology and medicine 20010201
Postnatal secretion of the subcommissural organ of the Meriones shawi: control of serotonin innervation. Brain research. Developmental brain research 20010131
Nitric oxide modulates lithium-induced conditioned taste aversion. Behavioural brain research 20010129
Occurrence of a unique protein toxin from the Indian King Cobra (Ophiophagus hannah) venom. Toxicon : official journal of the International Society on Toxinology 20010101
Acute antidepressant-like and antianxiety-like effects of tryptophan in mice. Pharmacology 20010101
Evaluation of genotoxity and mutagenicity of DL-p-chlorophenylalanine, its methyl ester and some N-acyl derivatives. Acta biologica Hungarica 20010101

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