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103429-31-8,MFCD00076708
Catalog No.:AA008RR3

103429-31-8 | CTOP

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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA008RR3
Chemical Name:
CTOP
CAS Number:
103429-31-8
Molecular Formula:
C50H67N11O11S2
Molecular Weight:
1062.2641
MDL Number:
MFCD00076708
SMILES:
NCCC[C@@H]1NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H](CSSC(C(NC(=O)[C@@H](NC1=O)[C@H](O)C)C(=O)N[C@H](C(=O)N)[C@H](O)C)(C)C)NC(=O)[C@@H](Cc1ccccc1)N)Cc1ccc(cc1)O)Cc1c[nH]c2c1cccc2
Properties
Computed Properties
 
Complexity:
1930  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
74  
Hydrogen Bond Acceptor Count:
15  
Hydrogen Bond Donor Count:
14  
Rotatable Bond Count:
16  
Undefined Atom Stereocenter Count:
10  
XLogP3:
0.5  

Literature

Title: Involvement of multiple µ-opioid receptor subtypes on the presynaptic or postsynaptic inhibition of spinal pain transmission.

Journal: Peptides 20140101

Title: Powerful inhibitory action of mu opioid receptors (MOR) on cholinergic interneuron excitability in the dorsal striatum.

Journal: Neuropharmacology 20131201

Title: Identification of a μ-δ opioid receptor heteromer-biased agonist with antinociceptive activity.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20130716

Title: Morphine inhibits sleep-promoting neurons in the ventrolateral preoptic area via mu receptors and induces wakefulness in rats.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20130401

Title: Opioids inhibit visceral afferent activation of catecholamine neurons in the solitary tract nucleus.

Journal: Neuroscience 20121011

Title: Opioidergic modulation of ethanol self-administration in the ventral pallidum.

Journal: Alcoholism, clinical and experimental research 20120201

Title: Erasure of a spinal memory trace of pain by a brief, high-dose opioid administration.

Journal: Science (New York, N.Y.) 20120113

Title: Oligodendrocyte responses to buprenorphine uncover novel and opposing roles of μ-opioid- and nociceptin/orphanin FQ receptors in cell development: implications for drug addiction treatment during pregnancy.

Journal: Glia 20120101

Title: Distinct mechanisms underlying pronociceptive effects of opioids.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20111116

Title: Neuroadaptation of GABAergic transmission in the central amygdala during chronic morphine treatment.

Journal: Addiction biology 20111001

Title: The effects of opioid receptor antagonists on electroacupuncture-produced anti-allodynia/hyperalgesia in rats with paclitaxel-evoked peripheral neuropathy.

Journal: Brain research 20110926

Title: Endogenous opioid peptides contribute to associative LTP in the hippocampal CA3 region.

Journal: Neurobiology of learning and memory 20110901

Title: Synergistic interaction between intrathecal ginsenosides and morphine on formalin-induced nociception in rats.

Journal: The journal of pain : official journal of the American Pain Society 20110701

Title: Nucleus accumbens facilitates nociception.

Journal: Experimental neurology 20110601

Title: Micro-opioid receptor activation in the basolateral amygdala mediates the learning of increases but not decreases in the incentive value of a food reward.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20110202

Title: G-protein-independent modulation of P-type calcium channels by mu-opioids in Purkinje neurons of rat.

Journal: Neuroscience letters 20100816

Title: Evidence for a role of opioids in epoxyeicosatrienoic acid-induced cardioprotection in rat hearts.

Journal: American journal of physiology. Heart and circulatory physiology 20100601

Title: Remifentanil post-conditioning attenuates cardiac ischemia-reperfusion injury via kappa or delta opioid receptor activation.

Journal: Acta anaesthesiologica Scandinavica 20100401

Title: Nociceptive behaviour upon modulation of mu-opioid receptors in the ventrobasal complex of the thalamus of rats.

Journal: Pain 20100301

Title: A prolonged protein kinase C-mediated, opioid-related antinociceptive effect of st John's Wort in mice.

Journal: The journal of pain : official journal of the American Pain Society 20100201

Title: Supraspinal Gbetagamma-dependent stimulation of PLCbeta originating from G inhibitory protein-mu opioid receptor-coupling is necessary for morphine induced acute hyperalgesia.

Journal: Journal of neurochemistry 20091001

Title: Bidirectional effects of fentanyl on dendritic spines and AMPA receptors depend upon the internalization of mu opioid receptors.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090801

Title: Roles of opioid receptor subtypes in mediating alcohol-seeking induced by discrete cues and context.

Journal: The European journal of neuroscience 20090801

Title: Ethanol-induced social facilitation in adolescent rats: role of endogenous activity at mu opioid receptors.

Journal: Alcoholism, clinical and experimental research 20090601

Title: The ventral pallidum is critically involved in the development and expression of morphine-induced sensitization.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20090301

Title: Tolerance to non-opioid analgesics in PAG involves unresponsiveness of medullary pain-modulating neurons in male rats.

Journal: The European journal of neuroscience 20090301

Title: Depression of C fibre-evoked spinal field potentials by the spinal delta opioid receptor is enhanced in the spinal nerve ligation model of neuropathic pain: involvement of the mu-subtype.

Journal: Neuropharmacology 20081201

Title: Inhibition of the development of morphine tolerance by a potent dual mu-delta-opioid antagonist, H-Dmt-Tic-Lys-NH-CH2-Ph.

Journal: Pharmacology, biochemistry, and behavior 20081001

Title: Roles of opioid receptor subtypes on the antinociceptive effect of intrathecal sildenafil in the formalin test of rats.

Journal: Neuroscience letters 20080815

Title: Intramuscular administration of morphine reduces mustard-oil-induced craniofacial-muscle pain behavior in lightly anesthetized rats.

Journal: European journal of pain (London, England) 20080401

Title: Molecular interaction in the mouse PAG between NMDA and opioid receptors in morphine-induced acute thermal nociception.

Journal: Journal of neurochemistry 20080401

Title: Essential role of mu opioid receptor in the regulation of delta opioid receptor-mediated antihyperalgesia.

Journal: Neuroscience 20071219

Title: Subdivision-specific responses of neurons in the nucleus of the tractus solitarius to activation of mu-opioid receptors in the rat.

Journal: Journal of neurophysiology 20071101

Title: Comparative analysis of mu-opioid receptor expression in immune and neuronal cells.

Journal: Journal of neuroimmunology 20070801

Title: Augmentation of spinal morphine analgesia and inhibition of tolerance by low doses of mu- and delta-opioid receptor antagonists.

Journal: British journal of pharmacology 20070701

Title: A Tyr-W-MIF-1 analog containing D-Pro2 discriminates among antinociception in mice mediated by different classes of mu-opioid receptors.

Journal: European journal of pharmacology 20070601

Title: Involvement of delta-and mu-opioid receptors in the delayed cerebral ischemic tolerance induced by repeated electroacupuncture preconditioning in rats.

Journal: Chinese medical journal 20070305

Title: In vivo pharmacological resultant analysis reveals noncompetitive interactions between opioid antagonists in the rat tail-withdrawal assay.

Journal: British journal of pharmacology 20061201

Title: Vagal afferent control of opioidergic effects in rat brainstem circuits.

Journal: The Journal of physiology 20060915

Title: The role of opioid receptor subtypes in the development of behavioral sensitization to ethanol.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060701

Title: Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060401

Title: Cannabinoid receptor type 2 agonists induce transcription of the mu-opioid receptor gene in Jurkat T cells.

Journal: Molecular pharmacology 20060401

Title: Reinforcing properties of ethanol in neonatal rats: involvement of the opioid system.

Journal: Behavioral neuroscience 20060401

Title: Peripheral mechanisms of intestinal dysmotility in the morphine tolerant and dependent rats.

Journal: Journal of physiology and pharmacology : an official journal of the Polish Physiological Society 20060301

Title: Endomorphin-2 and endomorphin-1 promote the extracellular amount of accumbal dopamine via nonopioid and mu-opioid receptors, respectively.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20060201

Title: Morphine activates Arc expression in the mouse striatum and in mouse neuroblastoma Neuro2A MOR1A cells expressing mu-opioid receptors.

Journal: Journal of neuroscience research 20051115

Title: Kinin and opioid receptors in the paratrigeminal nucleus modulate the somatosensory reflex to rat sciatic nerve stimulation.

Journal: Peptides 20050801

Title: Mu-opioid receptors are not involved in acute cocaine-induced locomotor activity nor in development of cocaine-induced behavioral sensitization in mice.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20050201

Title: Interactions among mu- and delta-opioid receptors, especially putative delta1- and delta2-opioid receptors, promote dopamine release in the nucleus accumbens.

Journal: Neuroscience 20050101

Title: Differential sensitivity of N- and P/Q-type Ca2+ channel currents to a mu opioid in isolectin B4-positive and -negative dorsal root ganglion neurons.

Journal: The Journal of pharmacology and experimental therapeutics 20041201

Title: Septopreoptic mu opioid receptor mediation of hindbrain glucoprivic inhibition of reproductive neuroendocrine function in the female rat.

Journal: Endocrinology 20041101

Title: RGSZ1 and GAIP regulate mu- but not delta-opioid receptors in mouse CNS: role in tachyphylaxis and acute tolerance.

Journal: Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20040601

Title: Fentanyl inhibits GABAergic neurotransmission to cardiac vagal neurons in the nucleus ambiguus.

Journal: Brain research 20040508

Title: Differential conditioned place preference responses to endomorphin-1 and endomorphin-2 microinjected into the posterior nucleus accumbens shell and ventral tegmental area in the rat.

Journal: The Journal of pharmacology and experimental therapeutics 20040501

Title: Deltorphin II enhances extracellular levels of dopamine in the nucleus accumbens via opioid receptor-independent mechanisms.

Journal: European journal of pharmacology 20040426

Title: Loss of vasomotor responsiveness to the mu-opioid receptor ligand endomorphin-1 in adjuvant monoarthritic rat knee joints.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20040401

Title: Opiate alkaloids and nitric oxide production in the nematode Ascaris suum.

Journal: The Journal of parasitology 20040201

Title: Estrogen-induced mu-opioid receptor internalization in the medial preoptic nucleus is mediated via neuropeptide Y-Y1 receptor activation in the arcuate nucleus of female rats.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040128

Title: Opioidergic modulation of excitability of rat trigeminal root ganglion neuron projections to the superficial layer of cervical dorsal horn.

Journal: Neuroscience 20040101

Title: Opiate alkaloids in Ascaris suum.

Journal: Acta biologica Hungarica 20040101

Title: Role of opioid receptors in cardioprotection of cold-restraint stress and morphine.

Journal: Journal of biomedical science 20040101

Title: Neurite outgrowth-stimulating activities of beta-casomorphins in Neuro-2a mouse neuroblastoma cells.

Journal: Bioscience, biotechnology, and biochemistry 20031201

Title: Effects of endogenous and synthetic opioid peptides on neutrophil function in vitro.

Journal: British journal of anaesthesia 20031001

Title: Delta opioid receptors are involved in morphine-induced inhibition of luteinizing hormone releasing hormone in SK-N-SH cells.

Journal: Neuropeptides 20031001

Title: Antinociceptive properties of oxymorphazole in the mouse.

Journal: European journal of pharmacology 20030725

Title: Identity of the putative delta1-opioid receptor as a delta-kappa heteromer in the mouse spinal cord.

Journal: European journal of pharmacology 20030425

Title: The presynaptic modulation of corticostriatal afferents by mu-opioids is mediated by K+ conductances.

Journal: European journal of pharmacology 20030221

Title: Ligand-induced mu opioid receptor endocytosis and recycling in enteric neurons.

Journal: Neuroscience 20030101

Title: Blockade of ventral pallidal opioid receptors induces a conditioned place aversion and attenuates acquisition of cocaine place preference in the rat.

Journal: Neuroscience 20030101

Title: Role of mu-opioid receptors in insulin release in the presence of inhibitory and excitatory secretagogues.

Journal: European journal of pharmacology 20020712

Title: The neuropeptide FF analogue, 1DMe, reduces in vivo dynorphin release from the rat spinal cord.

Journal: Journal of neurochemistry 20020501

Title: Roles of endogenous opioid peptides in modulation of nocifensive response to formalin.

Journal: The Journal of pharmacology and experimental therapeutics 20020201

Title: Long-term potentiation in direct perforant path projections to the hippocampal CA3 region in vivo.

Journal: Journal of neurophysiology 20020201

Title: Activation of mu-opioid receptors inhibits lordosis behavior in estrogen and progesterone-primed female rats.

Journal: Hormones and behavior 20020201

Title: Blockade of nigral and pallidal opioid receptors suppresses vacuous chewing movements in a rodent model of tardive dyskinesia.

Journal: Neuroscience 20020101

Title: Release of [Met5]enkephalin from the spinal cord by intraventricularly administered endomorphin-2, but not endomorphin-1 in the anesthetized rat.

Journal: Neuroscience letters 20011204

Title: Opioid receptor modulation of a metabolically sensitive ion channel in rat amygdala neurons.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20011201

Title: Progesterone blockade of estrogen activation of mu-opioid receptors regulates reproductive behavior.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010801

Title: Co-distribution of Fos- and mu opioid receptor immunoreactivity within the rat septopreoptic area and hypothalamus during acute glucose deprivation: effects of the mu receptor antagonist CTOP.

Journal: Neuroscience letters 20010629

Title: Rostral ventrolateral medullary opioid receptor subtypes in the inhibitory effect of electroacupuncture on reflex autonomic response in cats.

Journal: Autonomic neuroscience : basic & clinical 20010620

Title: Endomorphin-1: induction of motor behavior and lack of receptor desensitization.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20010615

Title: Differential effects of the novel non-peptidic opioid 4-tyrosylamido-6-benzyl-1,2,3,4 tetrahydroquinoline (CGPM-9) on in vitro rat t lymphocyte and macrophage functions.

Journal: Life sciences 20010504

Title: Spinal delta-opioid receptors mediate suppression of systemic SNC80 on excitability of the flexor reflex in normal and inflamed rat.

Journal: European journal of pharmacology 20010420

Title: Suppression of ethanol responding by centrally administered CTOP and naltrindole in AA and Wistar rats.

Journal: Alcoholism, clinical and experimental research 20010101

Title: Endomorphin and mu-opioid receptors in mouse brain mediate the analgesic effect induced by 2 Hz but not 100 Hz electroacupuncture stimulation.

Journal: Neuroscience letters 20001124

Title: Pharmacological examination of contractile responses of the guinea-pig isolated ileum produced by mu-opioid receptor antagonists in the presence of, and following exposure to, morphine.

Journal: British journal of pharmacology 20001101

Title: The effect of antagonists selective for mu- and delta-opioid receptor subtypes on alcohol consumption in C57BL/6 mice.

Journal: Alcohol (Fayetteville, N.Y.) 20001001

Title: G protein activation by endomorphins in the mouse periaqueductal gray matter.

Journal: Journal of biomedical science 20000101

Title: Delta-opioid ligands reverse alfentanil-induced respiratory depression but not antinociception.

Journal: The Journal of pharmacology and experimental therapeutics 19981201

Title: Endomorphin-1 and endomorphin-2 activate mu-opioid receptors in myenteric neurons of the guinea-pig small intestine.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19981201

Title: Endogenous opioid peptides acting at mu-opioid receptors in the dorsal horn contribute to midbrain modulation of spinal nociceptive neurons.

Journal: Journal of neurophysiology 19980201

Title: Evidence that spinal endogenous opioidergic systems control the expression of chronic pain-related behaviors in spinally injured rats.

Journal: Experimental brain research 19980101

Title: Naltrexone, naltrindole, and CTOP block cocaine-induced sensitization to seizures and death.

Journal: Peptides 19970101

Title: Neuronal basis for the hyperthermic effect of mu-opioid agonists in rats: decrease in temperature sensitivity of warm-sensitive hypothalamic neurons.

Journal: Neuroscience letters 19961101

Title: The mu-opioid receptor antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) [but not D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 (CTAP)] produces a nonopioid receptor-mediated increase in K+ conductance of rat locus ceruleus neurons.

Journal: Molecular pharmacology 19960901

Title: Effects of naloxone and D-Phe-Cys-Tyr-D-Trp-Arg-Thr-Pen-Thr-NH2 and the protein kinase inhibitors H7 and H8 on acute morphine dependence and antinociceptive tolerance in mice.

Journal: The Journal of pharmacology and experimental therapeutics 19960401

Title: Role of opioid receptors in the spinal antinociceptive effects of neuropeptide FF analogues.

Journal: British journal of pharmacology 19960201

Title: Mu- and delta-opioid receptor antagonists precipitate similar withdrawal phenomena in butorphanol and morphine dependence.

Journal: Neurochemical research 19960101

Title: Opioid effects on spinal [3H]5-hydroxytryptamine release are not related to their antinociceptive action.

Journal: European journal of pharmacology 19950105

Title: Mesolimbic dopamine neurotransmission is increased by administration of mu-opioid receptor antagonists.

Journal: European journal of pharmacology 19931012

Title: Differential regulation of adenylyl cyclase activity by mu and delta opioids in rat caudate putamen and nucleus accumbens.

Journal: The Journal of pharmacology and experimental therapeutics 19931001

Title: Involvement of mu-opioid receptors in alcohol drinking by alcohol-preferring AA rats.

Journal: Pharmacology, biochemistry, and behavior 19930701

Title: Go mediates the coupling of the mu opioid receptor to adenylyl cyclase in cloned neural cells and brain.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930501

Title: Neuroanatomical sites mediating the central actions of beta-endorphin as mapped by changes in glucose utilization: involvement of mu opioid receptors.

Journal: The Journal of pharmacology and experimental therapeutics 19920701

Title: Central effects of the potent and highly selective mu opioid antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) in mice.

Journal: European journal of pharmacology 19880610

Title: Cyclic somatostatin octapeptide analogues with high affinity and selectivity toward mu opioid receptors.

Journal: Life sciences 19860616

Title: H-D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2: a potent and selective antagonist opioid receptors.

Journal: NIDA research monograph 19860101

Title: Gulya K, et al. Central effects of the potent and highly selective μ opioid antagonist D-Phe-Cys-Tyr-D-Trp-Orn-Thr-Pen-Thr-NH2 (CTOP) in mice. Eur J Pharmacol. 1988 Jun 10;150(3):355-60.

Title: Badiani A, et al. Intra-VTA injections of the mu-opioid antagonist CTOP enhance locomotor activity. Brain Res. 1995 Aug 28;690(1):112-6.

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Tags:103429-31-8 Molecular Formula|103429-31-8 MDL|103429-31-8 SMILES|103429-31-8 CTOP