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17692-51-2,MFCD00153829
Catalog No.:AA0078S2

17692-51-2 | Metergoline

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25mg
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50mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0078S2
Chemical Name:
Metergoline
CAS Number:
17692-51-2
Molecular Formula:
C25H29N3O2
Molecular Weight:
403.5167
MDL Number:
MFCD00153829
SMILES:
O=C(OCc1ccccc1)NCC1CN(C)C2C(C1)c1cccc3c1c(C2)cn3C
Properties
Computed Properties
 
Complexity:
607  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
3.8  

Literature

Title: Cocaine modulates pathways for photic and nonphotic entrainment of the mammalian SCN circadian clock.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20120315

Title: 5-HT receptors as novel targets for optimizing pigmentary responses in dorsal skin melanophores of frog, Hoplobatrachus tigerinus.

Journal: British journal of pharmacology 20120301

Title: Using functional signatures to identify repositioned drugs for breast, myelogenous leukemia and prostate cancer.

Journal: PLoS computational biology 20120201

Title: Inverse agonism at α2A adrenoceptors augments the hypophagic effect of sibutramine in rats.

Journal: Obesity (Silver Spring, Md.) 20111001

Title: Serotonin mediated changes in corticotropin releasing factor mRNA expression and feeding behavior isolated to the hypothalamic paraventricular nuclei.

Journal: Neuroscience letters 20110712

Title: Analgesic and antineuropathic drugs acting through central cholinergic mechanisms.

Journal: Recent patents on CNS drug discovery 20110501

Title: Metergoline-induced cell death in Candida krusei.

Journal: Fungal biology 20110301

Title: Anxiolytic effects of a semipurified constituent of guaraná seeds on rats in the elevated T-maze test.

Journal: Planta medica 20110201

Title: Anatomical pathways involved in generating and sensing rhythmic whisker movements.

Journal: Frontiers in integrative neuroscience 20110101

Title: On the mechanism of the antidepressant-like action of group II mGlu receptor antagonist, MGS0039.

Journal: Psychopharmacology 20101201

Title: 5-hydroxy-L-tryptophan Suppressed Food Intake in Rats Despite an Increase in the Arcuate NPY Expression.

Journal: Experimental neurobiology 20101201

Title: Evaluation of [(11)C]metergoline as a PET radiotracer for 5HTR in nonhuman primates.

Journal: Bioorganic & medicinal chemistry 20101115

Title: In vitro synergistic effects of metergoline and antifungal agents against Candida krusei.

Journal: Mycoses 20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: The development and validation of a novel virtual screening cascade protocol to identify potential serotonin 5-HT(7)R antagonists.

Journal: Bioorganic & medicinal chemistry letters 20100415

Title: On the intrinsic regulation of neuropeptide Y release in the mammalian suprachiasmatic nucleus circadian clock.

Journal: The European journal of neuroscience 20100301

Title: A role for serotonin in the antidepressant activity of NG-Nitro-L-arginine, in the rat forced swimming test.

Journal: Pharmacology, biochemistry, and behavior 20100201

Title: Tonic serotonergic control of ingestive behaviours in the pigeon (Columba livia): the role of the arcopallium.

Journal: Behavioural brain research 20091228

Title: Antidepressant-like effects of glucagon-like peptide-2 in mice occur via monoamine pathways.

Journal: Behavioural brain research 20091201

Title: Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20091201

Title: cis-Urocanic acid stimulates primary human keratinocytes independently of serotonin or platelet-activating factor receptors.

Journal: The Journal of investigative dermatology 20091101

Title: The bovine mammary gland expresses multiple functional isoforms of serotonin receptors.

Journal: The Journal of endocrinology 20091001

Title: Genetic mapping of targets mediating differential chemical phenotypes in Plasmodium falciparum.

Journal: Nature chemical biology 20091001

Title: Serotonergic-postsynaptic receptors modulate gripping-induced immobility episodes in male taiep rats.

Journal: Synapse (New York, N.Y.) 20090901

Title: Human 5-HT7 receptor-induced inactivation of forskolin-stimulated adenylate cyclase by risperidone, 9-OH-risperidone and other 'inactivating antagonists'.

Journal: Molecular pharmacology 20090901

Title: Pharmacological analysis of the novel, rapid, and potent inactivation of the human 5-Hydroxytryptamine7 receptor by risperidone, 9-OH-Risperidone, and other inactivating antagonists.

Journal: Molecular pharmacology 20090201

Title: Panic disorder: is the PAG involved?

Journal: Neural plasticity 20090101

Title: Selective serotonin reuptake inhibitors: a review of its effects on intraocular pressure.

Journal: Current neuropharmacology 20081201

Title: The effects of metergoline and 8-OH-DPAT injections into arcuate nucleus and lateral hypothalamic area on feeding in female rats during the estrous cycle.

Journal: Physiology & behavior 20081020

Title: The structure of human serotonin 2c G-protein-coupled receptor bound to agonists and antagonists.

Journal: Journal of molecular graphics & modelling 20080801

Title: Physiology of the canine anoestrus and methods for manipulation of its length.

Journal: Reproduction in domestic animals = Zuchthygiene 20080701

Title: Anxiolytic-like action of MTEP expressed in the conflict drinking Vogel test in rats is serotonin dependent.

Journal: Neuropharmacology 20071101

Title: Possible involvement of endogenous 5-HT in aggravation of cerulein-induced acute pancreatitis in mice.

Journal: Journal of pharmacological sciences 20071101

Title: In vivo Schild regression analyses using nonselective 5-HT2C receptor antagonists in a rat operant behavioral assay.

Journal: Psychopharmacology 20070801

Title: Feeding behavior after metergoline or GR-46611 injections into the paraventricular nucleus of the hypothalamus in the pigeon.

Journal: Behavioural brain research 20070516

Title: Anxiolytic-like effect of group III mGlu receptor antagonist is serotonin-dependent.

Journal: Neuropharmacology 20070201

Title: Serotonin increases the phase shift of the circadian locomotor activity rhythm in mice after dark pulses in constant light conditions.

Journal: Folia biologica 20070101

Title: Systemic morphine produce antinociception mediated by spinal 5-HT7, but not 5-HT1A and 5-HT2 receptors in the spinal cord.

Journal: British journal of pharmacology 20061101

Title: Dopamine agonists, anti-progestins, anti-androgens, long-term-release GnRH agonists and anti-estrogens in canine reproduction: a review.

Journal: Theriogenology 20061001

Title: Reanalysis of constitutively active rat and human 5-HT7(a) receptors in HEK-293F cells demonstrates lack of silent properties for reported neutral antagonists.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20061001

Title: Anoestrus in the dog: a fascinating story.

Journal: Reproduction in domestic animals = Zuchthygiene 20060801

Title: Serotonergic mediation of constant light-potentiated nonphotic phase shifting of the circadian locomotor activity rhythm in Syrian hamsters.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20060701

Title: Effects of dopamine D1-like receptor agonists on food-maintained operant behavior in rats.

Journal: Behavioural pharmacology 20060601

Title: Clozapine modulates aromatic L-amino acid decarboxylase activity in mouse striatum.

Journal: The Journal of pharmacology and experimental therapeutics 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Potential vascular alpha1-adrenoceptor blocking properties of an array of 5-HT receptor ligands in the rat.

Journal: European journal of pharmacology 20060327

Title: Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.

Journal: Journal of natural products 20060301

Title: Selective and nonselective serotonin antagonists block the aversive stimulus properties of MK212 and m-chlorophenylpiperazine (mCPP) in mice.

Journal: Neuropharmacology 20051201

Title: 5-HT1B receptors modulate the feeding inhibitory effects of enterostatin.

Journal: Brain research 20051116

Title: Updated overview of the putative role of the serotoninergic system in obsessive-compulsive disorder.

Journal: Neuropsychiatric disease and treatment 20050901

Title: Lack of involvement of dopamine and serotonin during the orphanin FQ/Nociceptin (OFQ/N)-induced prolactin secretory response.

Journal: Life sciences 20050812

Title: Pharmacotherapy of seasonal affective disorder.

Journal: CNS spectrums 20050801

Title: Lamotrigine has an anxiolytic-like profile in the rat conditioned emotional response test of anxiety: a potential role for sodium channels?

Journal: Psychopharmacology 20050601

Title: Serotonin-induced enhancement of vasopressin and oxytocin secretion in rat neurohypophyseal tissue culture.

Journal: Regulatory peptides 20050415

Title: 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.

Journal: The Journal of pharmacology and experimental therapeutics 20050301

Title: Pharmacological characterisation of the thermogenic effect of bupropion.

Journal: European journal of pharmacology 20040913

Title: Involvement of mast cells in basal and neurotensin-induced intestinal absorption of taurocholate in rats.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20040801

Title: Serotonin antagonist-induced lowering of prolactin secretion does not affect the pattern of pulsatile secretion of follicle-stimulating hormone and luteinizing hormone in the bitch.

Journal: Reproduction (Cambridge, England) 20040801

Title: Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20040801

Title: Serotonin reuptake inhibitors do not prevent 5,7-dihydroxytryptamine-induced depletion of serotonin in rat brain.

Journal: Brain research 20040508

Title: Study of the behavioural responses related to the potential addictive properties of MDMA in mice.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20040301

Title: Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.

Journal: European journal of pharmacology 20040126

Title: Optimization of the pharmacophore model for 5-HT7R antagonism. Design and synthesis of new naphtholactam and naphthosultam derivatives.

Journal: Journal of medicinal chemistry 20031218

Title: Treatment of seasonal affective disorders.

Journal: Dialogues in clinical neuroscience 20031201

Title: Pharmacological characterization of a serotonin receptor (5-HT7) stimulating cAMP production in human corneal epithelial cells.

Journal: Investigative ophthalmology & visual science 20031101

Title: Serotonergic and histaminergic mechanisms involved in intralipid drinking?

Journal: Pharmacology, biochemistry, and behavior 20030901

Title: Midbrain raphe modulation of nonphotic circadian clock resetting and 5-HT release in the mammalian suprachiasmatic nucleus.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20030820

Title: gp49B1 suppresses stem cell factor-induced mast cell activation-secretion and attendant inflammation in vivo.

Journal: European journal of immunology 20030801

Title: Serotonin regulates rhythmic whisking.

Journal: Neuron 20030717

Title: Abortifacient and endocrine effects of metergoline in beagle bitches during the second half of gestation.

Journal: Theriogenology 20030501

Title: Serotonin receptors involved in vasopressin and oxytocin secretion.

Journal: Journal of neuroendocrinology 20030301

Title: Pharmacological characterization of an adenylyl cyclase-coupled 5-HT receptor in aplysia: comparison with mammalian 5-HT receptors.

Journal: Journal of neurophysiology 20030301

Title: Serotonergic signaling inhibits hyperalgesia induced by spinal cord damage.

Journal: Brain research 20030214

Title: 5-HT7 receptor-mediated relaxation of the oviduct in nonpregnant proestrus pigs.

Journal: European journal of pharmacology 20030214

Title: Further evidence that the discriminative stimulus properties of indorenate are mediated by 5-HT 1A/1B/2C receptors.

Journal: Pharmacology, biochemistry, and behavior 20030101

Title: Effect of fenfluramine on caloric intake and macronutrient selection in Lou/c rats during aging.

Journal: Neurobiology of aging 20030101

Title: Pharmacological activity of hyperforin acetate in rats.

Journal: Behavioural pharmacology 20021201

Title: Effects of metergoline on symptoms in women with premenstrual dysphoric disorder.

Journal: The American journal of psychiatry 20021101

Title: The antinociceptive effect of mirtazapine in mice is mediated through serotonergic, noradrenergic and opioid mechanisms.

Journal: Brain research bulletin 20020930

Title: Mechanism of the thermogenic effect of Metabolite 2 (BTS 54 505), a major pharmacologically active metabolite of the novel anti-obesity drug, sibutramine.

Journal: International journal of obesity and related metabolic disorders : journal of the International Association for the Study of Obesity 20020901

Title: Serotonin receptor blockade increases food intake and body weight after total gastrectomy in rats.

Journal: The Journal of surgical research 20020801

Title: Pregnancy termination in the bitch and queen.

Journal: Clinical techniques in small animal practice 20020801

Title: Serotonergic activation rescues reproductive function in fasted mice: does serotonin mediate the metabolic effects of leptin on reproduction?

Journal: Biology of reproduction 20020601

Title: Reproductive hormonal treatments for mood disorders in women.

Journal: Dialogues in clinical neuroscience 20020601

Title: Gonadal steroids, brain, and behavior: role of context.

Journal: Dialogues in clinical neuroscience 20020601

Title: Serotonin sets the day state in the neurons that control coupling between the optic lobe circadian pacemakers in the cricket Gryllus bimaculatus.

Journal: The Journal of experimental biology 20020501

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: Specific labelling of serotonin 5-HT(1B) receptors in rat frontal cortex with the novel, phenylpiperazine derivative, [3H]GR125,743. A pharmacological characterization.

Journal: Pharmacology, biochemistry, and behavior 20020401

Title: Estrous cycle and food availability affect feeding induced by amygdala 5-HT receptor blockade.

Journal: Pharmacology, biochemistry, and behavior 20020401

Title: Double-blind, placebo-controlled study of single-dose metergoline in depressed patients with seasonal affective disorder.

Journal: Journal of clinical psychopharmacology 20020401

Title: Role of 5-hT2C receptors in the hypophagic effect of m-CPP, ORG 37684 and CP-94,253 in the rat.

Journal: Progress in neuro-psychopharmacology & biological psychiatry 20020401

Title: Involvement of the serotonergic system in orexin-induced behavioral alterations in rats.

Journal: Regulatory peptides 20020315

Title: Muramyl dipeptide (MDP) and 5-HT receptors. Neuroimmunomodulatory effects of MDP are probably not mediated through 5-HT4 or 5-HT1A receptors.

Journal: Immunopharmacology and immunotoxicology 20020201

Title: Calcium-antagonistic activity of sumatriptan in the rat anococcygeus muscle.

Journal: Pharmacology 20020101

Title: Functional characterization of a novel serotonin receptor (5-HTap2) expressed in the CNS of Aplysia californica.

Journal: Journal of neurochemistry 20020101

Title: Comparison between two models of experimental anxiety in healthy volunteers and panic disorder patients.

Journal: Neuroscience and biobehavioral reviews 20011201

Title: A review of canine pseudocyesis.

Journal: Reproduction in domestic animals = Zuchthygiene 20011201

Title: The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20010601

Title: 5-HT receptor blockade in the posterior amygdala elicits feeding in female rats.

Journal: Neuroreport 20010417

Title: Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats.

Journal: Journal of psychopharmacology (Oxford, England) 20010301

Title: Serotonin, norepinephrine and dopamine involvement in the antidepressant action of hypericum perforatum.

Journal: Pharmacopsychiatry 20010301

Title: Pharmacological characterisation of the decrease in 5-HT synthesis in the mouse brain evoked by the selective serotonin re-uptake inhibitor citalopram.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20010201

Title: A role for serotonin in lipopolysaccharide-induced anorexia in rats.

Journal: Pharmacology, biochemistry, and behavior 20010201

Title: Activation of nicotinic receptors on GABAergic amacrine cells in the rabbit retina indirectly stimulates dopamine release.

Journal: Visual neuroscience 20010101

Title: Effects of serotoninergic drugs on tremor induced by physostigmine in rats.

Journal: Behavioural brain research 20000501

Title: The role of serotonin(2) receptors in mediating cocaine-induced convulsions.

Journal: Pharmacology, biochemistry, and behavior 20000401

Title: Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.

Journal: Journal of neurochemistry 19981101

Title: The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.

Journal: Molecular pharmacology 19980901

Title: Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.

Journal: Molecular pharmacology 19970901

Title: Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).

Journal: British journal of pharmacology 19970901

Title: Characterization of human serotonin 1D and 1B receptors using [3H]-GR-125743, a novel radiolabelled serotonin 5HT1D/1B receptor antagonist.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19970901

Title: Cloning and characterization of the guinea pig 5-HT1F receptor subtype: a comparison of the pharmacological profile to the human species homolog.

Journal: Neuropharmacology 19970101

Title: Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.

Journal: Neuropharmacology 19970101

Title: Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.

Journal: Molecular pharmacology 19961201

Title: Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.

Journal: Journal of neurochemistry 19961101

Title: The pharmacology of impulsive behaviour in rats: the effects of drugs on response choice with varying delays of reinforcement.

Journal: Psychopharmacology 19961101

Title: Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.

Journal: Journal of neurochemistry 19960101

Title: Cloning and characterisation of the human 5-HT5A serotonin receptor.

Journal: FEBS letters 19941205

Title: Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.

Journal: The Journal of biological chemistry 19931105

Title: Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930915

Title: Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.

Journal: The Journal of biological chemistry 19930825

Title: Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.

Journal: Molecular pharmacology 19930801

Title: Molecular cloning and functional expression of 5-HT1E-like rat and human 5-hydroxytryptamine receptor genes.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930315

Title: Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.

Journal: Molecular pharmacology 19930301

Title: Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.

Journal: Molecular pharmacology 19930301

Title: Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930115

Title: Molecular cloning of a serotonin receptor from human brain (5HT1E): a fifth 5HT1-like subtype.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19920615

Title: Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.

Journal: Molecular pharmacology 19910801

Title: Effect of metergoline, fenfluramine, and 8-OHDPAT on catalepsy induced by haloperidol or morphine.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19880801

Title: Antagonism of drug-induced yawning and penile erections in rats.

Journal: European journal of pharmacology 19860318

Title: Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 19850401

Title: Effect of metergoline on human anxiety.

Journal: Psychopharmacology 19850101

Title: Central antiserotonergic and antidopaminergic action of pirenperone, a putative 5-HT2 receptor antagonist.

Journal: Polish journal of pharmacology and pharmacy 19850101

Title: Neuropharmacology of the parasitic trematode, Schistosoma mansoni.

Journal: The American journal of tropical medicine and hygiene 19830101

Title: The influence of 5-HT receptor blocking agents on the behavioral effects of analgesics in rats.

Journal: Psychopharmacology 19800101

Title: Chronic treatment with antidepressant drugs: potentiation of apomorphine-induced aggressive behaviour in rats.

Journal: Neuroscience letters 19790801

Title: Determination of the role of serotonergic and cholinergic systems in apomorphine--induced aggressiveness in rats.

Journal: Polish journal of pharmacology and pharmacy 19790101

Title: Stimulating action of sulpiride and pimozide on prolactin release. Effect on bromocriptine, L-dopa and metergoline administration.

Journal: Acta endocrinologica 19771001

Title: Antony R Knight, et al. Pharmacological characterisation of the agonist radioligand binding site of 5-HT(2A), 5-HT(2B) and 5-HT(2C) receptors. Naunyn Schmiedebergs Arch Pharmacol. 2004 Aug;370(2):114-23.

Title: Jessica A. Knight, et al. Pharmacological Analysis of the Novel, Rapid, and Potent Inactivation of the Human 5-Hydroxytryptamine7 Receptor by Risperidone, 9-OH-Risperidone, and Other Inactivating Antagonists. Mol Pharmacol. 2009 Feb; 75(2): 374-380.

Title: Jun-ho Lee, et al. Metergoline inhibits the neuronal Nav1.2 voltage-dependent Na+ channels expressed in Xenopus oocytes. Acta Pharmacol Sin. 2014 Jul; 35(7): 862-868.

Title: P K Eide, et al. The behavioural response to intrathecal serotonin is changed by acute but not by repeated treatment with zimelidine or metergoline. Pharmacol Toxicol. 1991 Nov;69(5):361-4.

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