5'-Guanidinonaltrindole

5'-Guanidinonaltrindole

Systematic (IUPAC) name
5'-Guanidinyl-17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
ATC code	?
PubChem	CID 6604846
ChEMBL	CHEMBL330427 N
Synonyms	5'-Guanidinonaltrindole, GNTI
Chemical data
Formula	C27H29N5O3
Mol. mass	471.550 g/mol
SMILES	eMolecules & PubChem
N (what is this?)  (verify)

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

1. ^ Jones, RM; Portoghese, PS (2000). "5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist". European Journal of Pharmacology 396 (1): 49–52. doi:10.1016/S0014-2999(00)00208-9. PMID 10822054. 
2. ^ Negus, SS; Mello, NK; Linsenmayer, DC; Jones, RM; Portoghese, PS (2002). "Kappa opioid antagonist effects of the novel kappa antagonist 5'-guanidinonaltrindole (GNTI) in an assay of schedule-controlled behavior in rhesus monkeys". Psychopharmacology 163 (3–4): 412–9. doi:10.1007/s00213-002-1038-x. PMID 12373442. 
3. ^ Bruchas, MR; Yang, T; Schreiber, S; Defino, M; Kwan, SC; Li, S; Chavkin, C (2007). "Long-acting κ Opioid Antagonists Disrupt Receptor Signaling and Produce Noncompetitive Effects by Activating c-Jun N-terminal Kinase". The Journal of Biological Chemistry 282 (41): 29803–11. doi:10.1074/jbc.M705540200. PMC 2096775. PMID 17702750. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2096775. 
4. ^ Mague, SD; Pliakas, AM; Todtenkopf, MS; Tomasiewicz, HC; Zhang, Y; Stevens Jr, WC; Jones, RM; Portoghese, PS et al (2003). "Antidepressant-like effects of kappa-opioid receptor antagonists in the forced swim test in rats". The Journal of Pharmacology and Experimental Therapeutics 305 (1): 323–30. doi:10.1124/jpet.102.046433. PMID 12649385. 
5. ^ Obara, I; Mika, J; Schafer, MK; Przewlocka, B (2003). "Antagonists of the κ-opioid receptor enhance allodynia in rats and mice after sciatic nerve ligation". British Journal of Pharmacology 140 (3): 538–46. doi:10.1038/sj.bjp.0705427. PMC 1574046. PMID 12970097. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1574046.