| Revision as of 12:49, 26 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL').← Previous edit |
Latest revision as of 11:22, 9 November 2024 edit undoGraeme Bartlett (talk | contribs)Administrators249,716 edits added Category:Cyclopropyl compounds using HotCat |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Drugbox |
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| Verifiedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 457477907 |
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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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| IUPAC_name = 5'-Guanidinyl-17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan |
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| image = 5'-GNTI.png |
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| image = 5'-Guanidinonaltrindole.svg |
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| width = 240 |
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| width = 240 |
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| legal_US = |
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| legal_US = |
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| legal_status = |
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| legal_status = |
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| routes_of_administration = |
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| routes_of_administration = |
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<!--Pharmacokinetic data--> |
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<!--Pharmacokinetic data--> |
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| metabolism = |
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| metabolism = |
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| elimination_half-life = |
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| elimination_half-life = |
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| excretion = |
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| excretion = |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| IUPHAR_ligand = 1669 |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = |
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| CAS_number = |
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| ATC_prefix = |
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| ATC_prefix = |
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| ATC_suffix = |
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| ATC_suffix = |
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| PubChem = 6604846 |
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| PubChem = 6604846 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = |
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| DrugBank = |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = <!-- blanked - oldvalue: 330427 --> |
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| ChEMBL = 330427 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 21259050 |
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<!--Chemical data--> |
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| C=27 | H=29 | N=5 | O=3 |
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| C=27 | H=29 | N=5 | O=3 |
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| smiles = c1cc2c(cc1NC(=N)N)c3c(2)456CCN((5(C3)O)Cc7c6c(c(cc7)O)O4)CC8CC8 |
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| molecular_weight = 471.550 g/mol |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| smiles = C7CC7CN3CCC58c4c(ccc(O)c4OC28)CC3C5(O)Cc(c1c6)c2nc1ccc6NC(=N)N |
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| StdInChI = 1S/C27H29N5O3/c28-25(29)30-15-4-5-18-16(10-15)17-11-27(34)20-9-14-3-6-19(33)23-21(14)26(27,24(35-23)22(17)31-18)7-8-32(20)12-13-1-2-13/h3-6,10,13,20,24,31,33-34H,1-2,7-9,11-12H2,(H4,28,29,30)/t20-,24+,26+,27-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = VLNHDKDBGWXJEE-GYHUNEDQSA-N |
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| synonyms = 5'-Guanidinonaltrindole, GNTI |
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| synonyms = 5'-Guanidinonaltrindole, GNTI |
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}} |
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}} |
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'''5'-Guanidinonaltrindole''' ('''GNTI''') is an ] ] used in scientific research which is highly selective for the ] ]. It is 5x more potent and 500 times more selective than the commonly used κ-opioid antagonist ].<ref>{{cite journal | last1 = Jones | first1 = RM | last2 = Portoghese | first2 = PS | title = 5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist | journal = European journal of pharmacology | volume = 396 | issue = 1 | pages = 49–52 | year = 2000 | pmid = 10822054 | doi=10.1016/S0014-2999(00)00208-9}}</ref> It has a slow onset and long duration of action,<ref>{{cite journal | last1 = Negus | first1 = SS | last2 = Mello | first2 = NK | last3 = Linsenmayer | first3 = DC | last4 = Jones | first4 = RM | last5 = Portoghese | first5 = PS | title = Kappa opioid antagonist effects of the novel kappa antagonist 5'-guanidinonaltrindole (GNTI) in an assay of schedule-controlled behavior in rhesus monkeys | journal = Psychopharmacology | volume = 163 | issue = 3–4 | pages = 412–9 | year = 2002 | pmid = 12373442 | doi = 10.1007/s00213-002-1038-x }}</ref><ref>{{cite journal | last1 = Bruchas | first1 = MR | last2 = Yang | first2 = T | last3 = Schreiber | first3 = S | last4 = Defino | first4 = M | last5 = Kwan | first5 = SC | last6 = Li | first6 = S | last7 = Chavkin | first7 = C | title = Long-acting κ Opioid Antagonists Disrupt Receptor Signaling and Produce Noncompetitive Effects by Activating c-Jun N-terminal Kinase | journal = The Journal of biological chemistry | volume = 282 | issue = 41 | pages = 29803–11 | year = 2007 | pmid = 17702750 | pmc = 2096775 | doi = 10.1074/jbc.M705540200 }}</ref> and produces ] effects in animal studies.<ref>{{cite journal | last1 = Mague | first1 = SD | last2 = Pliakas | first2 = AM | last3 = Todtenkopf | first3 = MS | last4 = Tomasiewicz | first4 = HC | last5 = Zhang | first5 = Y | last6 = Stevens Jr | first6 = WC | last7 = Jones | first7 = RM | last8 = Portoghese | first8 = PS | last9 = Carlezon Jr | first9 = WA | title = Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats | journal = The Journal of pharmacology and experimental therapeutics | volume = 305 | issue = 1 | pages = 323–30 | year = 2003 | pmid = 12649385 | doi = 10.1124/jpet.102.046433 }}</ref> It also increases ] by interfering with the action of the κ-opioid peptide ].<ref>{{cite journal | last1 = Obara | first1 = I | last2 = Mika | first2 = J | last3 = Schafer | first3 = MK | last4 = Przewlocka | first4 = B | title = Antagonists of the κ-opioid receptor enhance allodynia in rats and mice after sciatic nerve ligation | journal = British journal of pharmacology | volume = 140 | issue = 3 | pages = 538–46 | year = 2003 | pmid = 12970097 | pmc = 1574046 | doi = 10.1038/sj.bjp.0705427 }}</ref> |
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'''5'-Guanidinonaltrindole''' ('''5'-GNTI''') is an ] ] used in scientific research which is highly selective for the ] ]. It is 5x more potent and 500 times more selective than the commonly used κ-opioid antagonist ].<ref>{{cite journal | vauthors = Jones RM, Portoghese PS | title = 5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist | journal = European Journal of Pharmacology | volume = 396 | issue = 1 | pages = 49–52 | date = May 2000 | pmid = 10822054 | doi = 10.1016/S0014-2999(00)00208-9 }}</ref> It has a slow onset and long duration of action,<ref>{{cite journal | vauthors = Negus SS, Mello NK, Linsenmayer DC, Jones RM, Portoghese PS | title = Kappa opioid antagonist effects of the novel kappa antagonist 5'-guanidinonaltrindole (GNTI) in an assay of schedule-controlled behavior in rhesus monkeys | journal = Psychopharmacology | volume = 163 | issue = 3–4 | pages = 412–9 | date = October 2002 | pmid = 12373442 | doi = 10.1007/s00213-002-1038-x | s2cid = 6342513 }}</ref><ref>{{cite journal | vauthors = Bruchas MR, Yang T, Schreiber S, Defino M, Kwan SC, Li S, Chavkin C | title = Long-acting kappa opioid antagonists disrupt receptor signaling and produce noncompetitive effects by activating c-Jun N-terminal kinase | journal = The Journal of Biological Chemistry | volume = 282 | issue = 41 | pages = 29803–11 | date = October 2007 | pmid = 17702750 | pmc = 2096775 | doi = 10.1074/jbc.M705540200 | doi-access = free }}</ref> and produces ] effects in animal studies.<ref>{{cite journal | vauthors = Mague SD, Pliakas AM, Todtenkopf MS, Tomasiewicz HC, Zhang Y, Stevens WC, Jones RM, Portoghese PS, Carlezon WA | s2cid = 7235990 | display-authors = 6 | title = Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 305 | issue = 1 | pages = 323–30 | date = April 2003 | pmid = 12649385 | doi = 10.1124/jpet.102.046433 }}</ref> It also increases ] by interfering with the action of the κ-opioid peptide ].<ref>{{cite journal | vauthors = Obara I, Mika J, Schafer MK, Przewlocka B | title = Antagonists of the kappa-opioid receptor enhance allodynia in rats and mice after sciatic nerve ligation | journal = British Journal of Pharmacology | volume = 140 | issue = 3 | pages = 538–46 | date = October 2003 | pmid = 12970097 | pmc = 1574046 | doi = 10.1038/sj.bjp.0705427 }}</ref> |
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In addition to activity at the KOR, 5'-GNTI has been found to act as a ] of the ] (] = 41 nM), and this may contribute to its "severe transient effects".<ref>{{cite journal | vauthors = Munro TA, Huang XP, Inglese C, Perrone MG, Van't Veer A, Carroll FI, Béguin C, Carlezon WA, Colabufo NA, Cohen BM, Roth BL | display-authors = 6 | title = Selective κ opioid antagonists nor-BNI, GNTI and JDTic have low affinities for non-opioid receptors and transporters | journal = PLOS ONE | volume = 8 | issue = 8 | pages = e70701 | year = 2013 | pmid = 23976952 | pmc = 3747596 | doi = 10.1371/journal.pone.0070701 | bibcode = 2013PLoSO...870701M | doi-access = free }}</ref> |
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== See also == |
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== References == |
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== References == |
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{{Reflist}} |
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<references /> |
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{{Opioid receptor modulators}} |
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{{opioids}} |
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{{Adrenergic receptor modulators}} |
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{{DEFAULTSORT:Guanidinonaltrindole, 5'-}} |
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{{DEFAULTSORT:Guanidinonaltrindole, 5'-}} |
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{{Analgesic-stub}} |
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