5'-Guanidinonaltrindole

5'-Guanidinonaltrindole
Clinical data
Synonyms	5'-Guanidinonaltrindole, GNTI
Identifiers
	IUPAC name 5'-Guanidinyl-17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan;
PubChem CID	6604846;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C27H29N5O3
Molar mass	471.550 g/mol
3D model (JSmol)	Interactive image;
	SMILES C7CC7CN3CCC58c4c(ccc(O)c4OC28)CC3C5(O)Cc(c1c6)c2nc1ccc6NC(=N)N;

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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.^[1] It has a slow onset and long duration of action,^[2]^[3] and produces antidepressant effects in animal studies.^[4] It also increases allodynia by interfering with the action of the κ-opioid peptide dynorphin.^[5]

References

↑ 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
↑ 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
↑ 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
↑ 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

Template:Opioids

Template:WikiDoc Sources

[1] 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

[2] 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

[3] 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

[4] 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

[5] 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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5'-Guanidinonaltrindole

Overview

References

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