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93515-00-5 | 2-Iodomelatonin
CAS No: 93515-00-5 Catalog No: AG00625M MDL No:
Product Description
Catalog Number:
AG00625M
Chemical Name:
2-Iodomelatonin
CAS Number:
93515-00-5
Molecular Formula:
C13H15IN2O2
Molecular Weight:
358.1749
IUPAC Name:
N-[2-(2-iodo-5-methoxy-1H-indol-3-yl)ethyl]acetamide
InChI:
InChI=1S/C13H15IN2O2/c1-8(17)15-6-5-10-11-7-9(18-2)3-4-12(11)16-13(10)14/h3-4,7,16H,5-6H2,1-2H3,(H,15,17)
InChI Key:
FJDDSMSDZHURBJ-UHFFFAOYSA-N
SMILES:
COc1ccc2c(c1)c(CCNC(=O)C)c([nH]2)I
Properties
Complexity:
301
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
358.018g/mol
Formal Charge:
0
Heavy Atom Count:
18
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
358.179g/mol
Monoisotopic Mass:
358.018g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
54.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.3
Literature
| Title | Journal |
|---|---|
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| Melatonin receptors in brain areas and ocular tissues of the teleost Tinca tinca: characterization and effect of temperature. | General and comparative endocrinology 20080201 |
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| Signaling mechanisms of melatonin in antiproliferation of hormone-refractory 22Rv1 human prostate cancer cells: implications for prostate cancer chemoprevention. | Journal of pineal research 20070301 |
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| Changes in melatonin receptors in relation to the development of scoliosis in pinealectomized chickens. | Spine 20060815 |
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| Ligand binding to the human MT2 melatonin receptor: the role of residues in transmembrane domains 3, 6, and 7. | Biochemical and biophysical research communications 20050708 |
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| Effects of temperature on 2-[125I]-iodomelatonin binding to melatonin receptors in the neural retina of the frog Rana perezi. | Journal of pineal research 20050401 |
| 2-iodomelatonin prevents apoptosis of cerebellar granule neurons via inhibition of A-type transient outward K+ currents. | Journal of pineal research 20050101 |
| Binding characteristics and daily rhythms of melatonin receptors are distinct in the retina and the brain areas of the European sea bass retina (Dicentrarchus labrax). | Brain research 20041217 |
| Molecular modeling of human MT2 melatonin receptor: the role of Val204, Leu272 and Tyr298 in ligand binding. | Journal of neurochemistry 20041101 |
| Inhibitory effect of melatonin on alpha1-adrenergic-induced vasoconstriction in mesenteric beds of spontaneously hypertensive rats. | American journal of hypertension 20040401 |
| Melatonin binding sites in the brain of European sea bass (Dicentrarchus labrax). | Zoological science 20040401 |
| Melatonin receptor agonist 2-iodomelatonin prevents apoptosis of cerebellar granule neurons via K(+) current inhibition. | Journal of pineal research 20040301 |
| Characterization of melatonin binding sites in the brain and retina of the frog Rana perezi. | General and comparative endocrinology 20040201 |
| Melatonin attenuates rat carotid chemoreceptor response to hypercapnic acidosis. | Journal of pineal research 20040101 |
| Melatonin in animal models. | Dialogues in clinical neuroscience 20031201 |
| Melatonin prevents apoptosis and enhances HSP27 mRNA expression induced by heat shock in HL-60 cells: possible involvement of the MT2 receptor. | Journal of pineal research 20031101 |
| Melatonin receptor signaling in pregnant and nonpregnant rat uterine myocytes as probed by large conductance Ca2+-activated K+ channel activity. | Molecular endocrinology (Baltimore, Md.) 20031001 |
| Melatonin modulates secretion of growth hormone and prolactin by trout pituitary glands and cells in culture. | Endocrinology 20031001 |
| Melatonin attenuates alpha-adrenergic-induced contractions by increasing the release of vasoactive intestinal peptide in isolated rat penile bulb. | Urological research 20030801 |
| Melatonin-induced calcium signaling in clusters of human and rat duodenal enterocytes. | American journal of physiology. Gastrointestinal and liver physiology 20030601 |
| New selective ligands of human cloned melatonin MT1 and MT2 receptors. | Naunyn-Schmiedeberg's archives of pharmacology 20030601 |
| Melatonin inhibits rat medial vestibular nucleus neuron activity in vitro. | Neuroscience letters 20030508 |
| Melatonin biological activity and binding sites in human melanoma cells. | Journal of pineal research 20030501 |
| Three-dimensional quantitative structure-activity relationship studies on selected MT1 and MT2 melatonin receptor ligands: requirements for subtype selectivity and intrinsic activity modulation. | Journal of medicinal chemistry 20030410 |
| Design and synthesis of 3-phenyl tetrahydronaphthalenic derivatives as new selective MT2 melatoninergic ligands. | Bioorganic & medicinal chemistry 20030306 |
| Synthesis of new arylalkoxy amido derivatives as melatoninergic ligands. | Bioorganic & medicinal chemistry 20030306 |
| mt1 Melatonin receptor in the primate adrenal gland: inhibition of adrenocorticotropin-stimulated cortisol production by melatonin. | The Journal of clinical endocrinology and metabolism 20030101 |
| Melatonin receptors in human fetal brain: 2-[(125)I]iodomelatonin binding and MT1 gene expression. | Journal of pineal research 20021101 |
| Variations of mt1 melatonin receptor density in the rat uterus during decidualization, the estrous cycle and in response to exogenous steroid treatment. | Journal of pineal research 20021001 |
| MT1 melatonin receptor mRNA expression exhibits a circadian variation in the rat suprachiasmatic nuclei. | Brain research 20020809 |
| Melatonin's unique radical scavenging properties - roles of its functional substituents as revealed by a comparison with its structural analogs. | Journal of pineal research 20020801 |
| Melatonin and prostate cancer cell proliferation: interplay with castration, epidermal growth factor, and androgen sensitivity. | The Prostate 20020701 |
| 2[125I]Iodomelatonin binding and interaction with beta-adrenergic signaling in chick heart/coronary artery physiology. | Journal of pineal research 20020501 |
| Desensitization of pigment granule aggregation in Xenopus leavis melanophores: melatonin degradation rather than receptor down-regulation is responsible. | Journal of neurochemistry 20020501 |
| Synthesis of nitroindole derivatives with high affinity and selectivity for melatoninergic binding sites MT(3). | Journal of medicinal chemistry 20020425 |
| Daily morphological variations in the viscacha (Lagostomus maximus maximus) retina. Probable local modulatory action of melatonin. | The Anatomical record 20020401 |
| Receptor-mediated modulation of avian caecal muscle contraction by melatonin: role of tyrosine protein kinase. | Journal of pineal research 20020401 |
| Melatonin mt1 and MT2 receptors stimulate c-Jun N-terminal kinase via pertussis toxin-sensitive and -insensitive G proteins. | Cellular signalling 20020301 |
| Molecular determinants for the differential coupling of Galpha(16) to the melatonin MT1, MT2 and Xenopus Mel1c receptors. | Journal of neurochemistry 20020301 |
| First cloning and functional characterization of a melatonin receptor in fish brain: a novel one? | Journal of pineal research 20020301 |
| 2[125I]Iodomelatonin binding sites in guinea pig platelets. | Journal of pineal research 20020301 |
| Melatonin. | Dialogues in clinical neuroscience 20020301 |
| Activation of melatonin receptor increases a delayed rectifier K+ current in rat cerebellar granule cells. | Brain research 20011102 |
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| Down-regulation of mt1 melatonin receptors in rat ovary following estrogen exposure. | Life sciences 20010525 |
| Serine residues 110 and 114 are required for agonist binding but not antagonist binding to the melatonin MT(1) receptor. | Biochemical and biophysical research communications 20010420 |
| Changes in binding of iodomelatonin to membranes of Leydig cells and steroidogenesis after prolonged in vitro exposure to melatonin. | International journal of andrology 20010401 |
| Expression and functional characterization of the mt1 melatonin receptor from rat brain in Xenopus oocytes: evidence for coupling to the phosphoinositol pathway. | Journal of pineal research 20010401 |
| Food intake inhibition by melatonin in goldfish (Carassius auratus). | Physiology & behavior 20010401 |
| Synthesis, pharmacological characterization and QSAR studies on 2-substituted indole melatonin receptor ligands. | Bioorganic & medicinal chemistry 20010401 |
| N1E-115 mouse neuroblastoma cells express MT1 melatonin receptors and produce neurites in response to melatonin. | Biochimica et biophysica acta 20010115 |
| Melatonin and its analogs potentiate the nifedipine-sensitive high-voltage-activated calcium current in the chick embryonic heart cells. | Journal of pineal research 20010101 |
| Modulation of blood glucose by melatonin: a direct action on melatonin receptors in mouse hepatocytes. | Biological signals and receptors 20010101 |
| A new melatonin receptor ligand with mt1-agonist and MT2-antagonist properties. | Journal of pineal research 20001101 |
| Pharmacological characterization of human recombinant melatonin mt(1) and MT(2) receptors. | British journal of pharmacology 20000301 |
| GR196429: a nonindolic agonist at high-affinity melatonin receptors. | The Journal of pharmacology and experimental therapeutics 19980601 |
| Melatonin receptor antagonists that differentiate between the human Mel1a and Mel1b recombinant subtypes are used to assess the pharmacological profile of the rabbit retina ML1 presynaptic heteroreceptor. | Naunyn-Schmiedeberg's archives of pharmacology 19970301 |
| Characterization of a retinal melatonin receptor. | The Journal of pharmacology and experimental therapeutics 19850801 |
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