5'-Guanidinonaltrindole

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IUPAC_name = 5'-Guanidinyl-17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan


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synonyms = 5'-Guanidinonaltrindole, GNTI
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PubChem = 6604846
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C = 27 | H = 29 | N = 5 | O = 3
molecular_weight = 471.550 g/mol
smiles = C7CC7CN3CCC58c4c(ccc(O)c4OC28)CC3C5(O)Cc(c1c6)c2nc1ccc6NC(=N)N
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5'-Guanidinonaltrindole (GNTI) is an opioid antagonist used in scientific research which is highly selective for the κ opioid receptor. It is 5x more potent and 500 times more selective than the commonly used κ-opioid antagonist norbinaltorphimine. [Jones RM, Portoghese PS. 5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist. "European Journal of Pharmacology". 2000 May 12;396(1):49-52. PMID 10822054] It has a slow onset and long duration of action, [Negus SS, Mello NK, Linsenmayer DC, Jones RM, Portoghese PS. Kappa opioid antagonist effects of the novel kappa antagonist 5'-guanidinonaltrindole (GNTI) in an assay of schedule-controlled behavior in rhesus monkeys. "Psychopharmacology (Berlin)". 2002 Oct;163(3-4):412-9. PMID 12373442] [Bruchas MR, Yang T, Schreiber S, Defino M, Kwan SC, Li S, Chavkin C. Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase. "Journal of Biological Chemistry". 2007 Oct 12;282(41):29803-11. PMID 17702750] and produces antidepressant effects in animal studies. [Mague SD, Pliakas AM, Todtenkopf MS, Tomasiewicz HC, Zhang Y, Stevens WC Jr, Jones RM, Portoghese PS, Carlezon WA Jr. Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats. "Journal of Pharmacology and Experimental Therapeutics". 2003 Apr;305(1):323-30. PMID 12649385] It also increases allodynia by interfering with the action of the κ-opioid peptide dynorphin. [Obara I, Mika J, Schafer MK, Przewlocka B. Antagonists of the kappa-opioid receptor enhance allodynia in rats and mice after sciatic nerve ligation. "British Journal of Pharmacology". 2003 Oct;140(3):538-46. PMID 12970097]

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