5'-Guanidinonaltrindole

5'-Guanidinonaltrindole (5'-GNTI) is an opioid antagonist used in scientific research which is highly selective for the κ opioid receptor.^[1] It is more potent and selective than the commonly used κ-opioid antagonist norbinaltorphimine.^[2] It has a slow onset and long duration of action,^[3][4] and produces antidepressant effects in animal studies.^[5] It also increases allodynia by interfering with the action of the κ-opioid peptide dynorphin.^[6]

5'-Guanidinonaltrindole

Clinical data
Other names	5'-Guanidinonaltrindole, GNTI
Identifiers
IUPAC name 5'-Guanidinyl-17-(cyclopropylmethyl)-6,7-dehydro-4,5α-epoxy-3,14-dihydroxy-6,7-2',3'-indolomorphinan
PubChem CID	6604846
IUPHAR/BPS	1669
ChemSpider	21259050 N
ChEMBL	ChEMBL330427 N
CompTox Dashboard (EPA)	DTXSID101018243
Chemical and physical data
Formula	C27H29N5O3
Molar mass	471.561 g·mol−1
3D model (JSmol)	Interactive image
SMILES c1cc2c(cc1NC(=N)N)c3c([nH]2)[C@H]4[C@@]56CCN([C@@H]([C@@]5(C3)O)Cc7c6c(c(cc7)O)O4)CC8CC8
InChI InChI=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 N Key:VLNHDKDBGWXJEE-GYHUNEDQSA-N N
NY (what is this?)  (verify)

In addition to activity at the KOR, 5'-GNTI has been found to act as a positive allosteric modulator of the α_1A-adrenergic receptor (EC₅₀ = 41 nM), and this may contribute to its "severe transient effects".^[1]

See also

• 6'-Guanidinonaltrindole
• Binaltorphimine
• JDTic