Zacopride

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IUPAC_name = 4-amino-N-(1-azabicyclo [2.2.2] octan-8-yl)-5-chloro-2-methoxybenzamide


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CAS_number = 90182-92-6
synonyms = Zacopride
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PubChem = 108182
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C = 15 | H = 20 | Cl = 1 | N = 3 | O = 2
molecular_weight = 309.791 g/mol
smiles = COC1=CC(=C(C=C1C(=O)NC2CN3CCC2CC3)Cl)N
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Zacopride is a potent antagonist at the 5HT₃ receptor [Smith WW, Sancilio LF, Owera-Atepo JB, Naylor RJ, Lambert L. Zacopride, a potent 5-HT3 antagonist. "Journal of Pharmacy and Pharmacology". 1988 Apr;40(4):301-2. PMID 2900319] and an agonist at the 5HT₄ receptor. [Lefebvre H, Contesse V, Delarue C, Soubrane C, Legrand A, Kuhn JM, Wolf LM, Vaudry H. Effect of the serotonin-4 receptor agonist zacopride on aldosterone secretion from the human adrenal cortex: in vivo and in vitro studies. "Journal of Clinical Endocrinology and Metabolism". 1993 Dec;77(6):1662-6. PMID 8263156] It has anxiolytic [Costall B, Domeney AM, Gerrard PA, Kelly ME, Naylor RJ. Zacopride: anxiolytic profile in rodent and primate models of anxiety. "Journal of Pharmacy and Pharmacology". 1988 Apr;40(4):302-5. PMID 2900320] and nootropic effects in animal models, [Fontana DJ, Daniels SE, Eglen RM, Wong EH. Stereoselective effects of (R)- and (S)-zacopride on cognitive performance in a spatial navigation task in rats. "Neuropharmacology". 1996 Mar;35(3):321-7. PMID 8783207] with the (R) enantiomer being the more active form. [Young R, Johnson DN. Anxiolytic-like activity of R(+)- and S(-)-zacopride in mice. "European Journal of Pharmacology". 1991 Aug 29;201(2-3):151-5. PMID 1686755] It also has pro-respiratory effects, both reducing sleep apnoea [Carley DW, Depoortere H, Radulovacki M. R-zacopride, a 5-HT3 antagonist/5-HT4 agonist, reduces sleep apneas in rats. "Pharmacology, Biochemistry and Behaviour". 2001 May-Jun;69(1-2):283-9. PMID 11420096] and reversing opioid-induced respiratory depression in animal studies. [Meyer LC, Fuller A, Mitchell D. Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats. "American Journal of Physiology. Regulatory, Integrative and Comparative Physiology". 2006 Feb;290(2):R405-13. PMID 16166206]

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