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G3416

5′-Guanidinonaltrindole di(trifluoroacetate) salt hydrate

Name: 5′-Guanidinonaltrindole di(trifluoroacetate) salt hydrate
Brand: SIGMA

solid, ≥98% (HPLC)

Synonym(s):

GNTI

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About This Item

Empirical Formula (Hill Notation):

C₂₇H₂₉N₅O₃ · 2C₂HF₃O₂ · xH₂O

CAS Number:

219655-57-9

Molecular Weight:

699.60 (anhydrous basis)

UNSPSC Code:

12352202

PubChem Substance ID:

24278454

NACRES:

NA.77

assay

≥98% (HPLC)

form

solid

solubility

H₂O: 30 mg/mL

storage temp.

2-8°C

Gene Information

human ... OPRK1(4986)

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)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Potent and selective indolomorphinan antagonists of the kappa-opioid receptor.

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

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)

5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist.

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