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6'-Guanidinonaltrindole

From Wikipedia, the free encyclopedia
6′-Guanidinonaltrindole
Names
IUPAC name
N-[17-(Cyclopropylmethyl)-3,14-dihydroxy-1′H-4,5α-epoxyindolo[2′,3′:6,7]morphinan-6′-yl]guanidine
Systematic IUPAC name
N-[(4bS,8R,8aS,14bR)-7-(Cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methano[1]benzofuro[2,3-b]pyrido[4,3-c]carbazol-12-yl]guanidine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C27H29N5O3/c28-25(29)30-15-4-5-16-17-11-27(34)20-9-14-3-6-19(33)23-21(14)26(27,7-8-32(20)12-13-1-2-13)24(35-23)22(17)31-18(16)10-15/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
    Key: XDKOGAAFSBGLBO-GYHUNEDQSA-N
  • c1cc2c(cc1NC(=N)N)[nH]c3c2CC4(C5Cc6ccc(c7c6C4(C3O7)CCN5CC8CC8)O)O
Properties
C27H29N5O3
Molar mass471.561 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

6′-Guanidinonaltrindole (6′-GNTI) is aκδ-opioid receptor selective ligand used in scientific research.[1]

With 6′-GNTI, evidence was provided for the first time thatreceptor oligomerization plays functional role in living organisms.[2]

6′-GNTI is an extremelybiased agonist of the κ-opioid receptor.[1] It is a potentpartial agonist of theG protein pathway but does not recruit theβ-arrestin pathway.[1] Due to itsfunctional selectivity for the G protein pathway, 6′-GNTI functions as anantagonist of nonbiased KOR agonists on the β-arrestin pathway.[1] It is thought that 6′-GTNI may be able to produceanalgesia withoutdysphoria and with a lower incidence oftolerance.[1]

See also

[edit]

References

[edit]
  1. ^abcdeRives, ML; Rossillo, M; Liu-Chen, LY; Javitch, JA (2012)."6′-Guanidinonaltrindole (6′-GNTI) is a G protein–biased κ-opioid receptor agonist that inhibits arrestin recruitment".J Biol Chem.287 (32):27050–4.doi:10.1074/jbc.C112.387332.PMC 3411045.PMID 22736766.
  2. ^Waldhoer M, Fong J, Jones RM, Lunzer MM, Sharma SK, Kostenis E, Portoghese PS, Whistler JL (June 2005)."A heterodimer-selective agonist shows in vivo relevance of G protein–coupled receptor dimers".Proc. Natl. Acad. Sci. U.S.A.102 (25):9050–5.Bibcode:2005PNAS..102.9050W.doi:10.1073/pnas.0501112102.PMC 1157030.PMID 15932946.
μ-opioid
(MOR)
Agonists
(abridged;
full list)
Antagonists
δ-opioid
(DOR)
Agonists
Antagonists
κ-opioid
(KOR)
Agonists
Antagonists
Nociceptin
(NOP)
Agonists
Antagonists
Others


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