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G3416

Sigma-Aldrich

5′-Guanidinonaltrindole di(trifluoroacetate) salt hydrate

solid, ≥98% (HPLC)

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Synonym(s):
GNTI
Empirical Formula (Hill Notation):
C27H29N5O3 · 2C2HF3O2 · xH2O
CAS Number:
Molecular Weight:
699.60 (anhydrous basis)
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

solubility

H2O: 30 mg/mL

storage temp.

2-8°C

Gene Information

human ... OPRK1(4986)

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assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: 30 mg/mL

solubility

H2O: >5 mg/mL

solubility

H2O: >5 mg/mL

solubility

DMSO: >5 mg/mL, H2O: insoluble

Gene Information

human ... OPRK1(4986)

Gene Information

-

Gene Information

-

Gene Information

-

Application

5′-Guanidinonaltrindole di(trifluoroacetate) salt hydrate (GNTI) has been used as a selective κ opioid receptor antagonist:
  • to study the influence of opioid receptor types on the anti-hyperalgesic effect of dipeptidyl peptidase 4 (DPP4) inhibitors in inflammation
  • to study the role of κ opioid receptor in the forebrain-dependent associative task, Whisker-Trace Eyeblink conditioning (WTEB)
  • to validate its inhibitory actions on Akt kinase activities

Biochem/physiol Actions

5′-Guanidinonaltrindole di(trifluoroacetate) (GNTI) is a 5‘-guanidine derivative and a selective κ opiate receptor antagonist. It is five-fold more potent and 500-fold more selective than norbinaltorphimine (nor-BNI) for the κ opioid receptor in smooth muscle preparations.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

Sold under US Patent No. 6,500,824.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Pathology and glia type specific changes of the DPP4 activity in the spinal cord contributes to the development and maintenance of hyperalgesia and shapes opioid signalling in chronic pain states
KiralyK, et al.
Scientific reports (2017)
Pathology and glia type specific changes of the DPP4 activity in the spinal cord contributes to the development and maintenance of hyperalgesia and shapes opioid signalling in chronic pain states
KiralyK, et al.
Scientific Reports (2017)
C T Chan et al.
Molecular imaging and biology, 11(3), 144-158 (2008-12-03)
Protein phosphorylation mediated by protein kinases controls numerous cellular processes. A genetically encoded, generalizable split firefly luciferase (FL)-assisted complementation system was developed for noninvasive monitoring phosphorylation events and efficacies of kinase inhibitors in cell culture and in small living subjects
R M Jones et al.
European journal of pharmacology, 396(1), 49-52 (2000-05-24)
5'-Guanidinonaltrindole (GNTI) possesses 5-fold greater opioid antagonist potency (K(e)=0.04 nM) and an order of magnitude greater selectivity (selectivity ratios >500) than the prototypical kappa-opioid receptor antagonist, norbinaltorphimine, in smooth muscle preparations. Binding and functional studies conducted on cloned human opioid
W C Stevens et al.
Journal of medicinal chemistry, 43(14), 2759-2769 (2000-07-14)
The indole moiety in the delta-opioid antagonist, naltrindole (2, NTI), was employed as a scaffold to hold an "address" for interaction with the kappa-opioid receptor. The attachment of the address to the 5'-position of the indole moiety was based on

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