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MedKoo Cat#: 563681 | Name: GNTI TFA
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

GNTI TFA is a selective kappa opioid receptor antagonist.

Chemical Structure

GNTI TFA
GNTI TFA
CAS#219655-57-9 (TFA)

Theoretical Analysis

MedKoo Cat#: 563681

Name: GNTI TFA

CAS#: 219655-57-9 (TFA)

Chemical Formula: C31H31F6N5O7

Exact Mass: 0.0000

Molecular Weight: 699.61

Elemental Analysis: C, 53.22; H, 4.47; F, 16.29; N, 10.01; O, 16.01

Price and Availability

Size Price Availability Quantity
5mg USD 450.00 2 Weeks
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Related CAS #
219655-56-8 (free base) 219655-57-9 (TFA)
Synonym
GNTI TFA; GNTI bis-TFA salt; GNTI TFA salt; Guanidinyl naltrindole; GNTI di-trifluoroacetate;
IUPAC/Chemical Name
2-((4bS,8R,8aS,14bR)-7-(cyclopropylmethyl)-1,8a-dihydroxy-5,6,7,8,8a,9,14,14b-octahydro-4,8-methanobenzofuro[2,3-a]pyrido[4,3-b]carbazol-11-yl)guanidine bis(2,2,2-trifluoroacetate)
InChi Key
LGXCKWXJRPYRLW-AWCPWCJTSA-N
InChi Code
InChI=1S/C27H29N5O3.2C2HF3O2/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;2*3-2(4,5)1(6)7/h3-6,10,13,20,24,31,33-34H,1-2,7-9,11-12H2,(H4,28,29,30);2*(H,6,7)/t20-,24+,26+,27-;;/m1../s1
SMILES Code
OC(C=C1)=C(O2)C3=C1C[C@@H]4[C@]5(O)CC(C6=C(C=CC(/N=C(N)\N)=C6)N7)=C7[C@H]2[C@@]53CCN4CC8CC8.O=C(O)C(F)(F)F.O=C(O)C(F)(F)F
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
GNTI TFA is a selective kappa opioid receptor antagonist.
In vitro activity:
In cells pretreated with BK (10 μM, 15 min), 6′-GNTI inhibited PGE2-stimulated adenylyl cyclase activity with an EC50 of 2 nM (pEC50 8.72 ± 0.14, n = 4) and a maximal inhibition of 76 ± 8. Reference: Mol Pharmacol. 2012 Feb;81(2):264-72. https://pubmed.ncbi.nlm.nih.gov/22072818/
In vivo activity:
In a separate cohort of rats, this study tested the effects of the selective KOR antagonist 5′GNTI on opioid withdrawal-induced hyperalgesia. 5′GNTI reversed heroin withdrawal-induced hyperalgesia in females (F5,40 = 4.141, p = 0.004; Fig. 4C) and males (F5,40 = 9.095, p < 0.0001; Fig. 4E). Reference: Neurobiol Stress. 2021 Apr 14;14:100325. https://pubmed.ncbi.nlm.nih.gov/33997152/

Preparing Stock Solutions

The following data is based on the product molecular weight 699.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Berg KA, Rowan MP, Gupta A, Sanchez TA, Silva M, Gomes I, McGuire BA, Portoghese PS, Hargreaves KM, Devi LA, Clarke WP. Allosteric interactions between δ and κ opioid receptors in peripheral sensory neurons. Mol Pharmacol. 2012 Feb;81(2):264-72. doi: 10.1124/mol.111.072702. Epub 2011 Nov 9. PMID: 22072818; PMCID: PMC3263945. 2. Reeves PJ, Callewaert N, Contreras R, Khorana HG. Structure and function in rhodopsin: high-level expression of rhodopsin with restricted and homogeneous N-glycosylation by a tetracycline-inducible N-acetylglucosaminyltransferase I-negative HEK293S stable mammalian cell line. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13419-24. doi: 10.1073/pnas.212519299. Epub 2002 Oct 7. PMID: 12370423; PMCID: PMC129688. 3. Marchette RCN, Gregory-Flores A, Tunstall BJ, Carlson ER, Jackson SN, Sulima A, Rice KC, Koob GF, Vendruscolo LF. κ-Opioid receptor antagonism reverses heroin withdrawal-induced hyperalgesia in male and female rats. Neurobiol Stress. 2021 Apr 14;14:100325. doi: 10.1016/j.ynstr.2021.100325. PMID: 33997152; PMCID: PMC8095052. 4. Shoaib RM, Ahmad KA, Wang YX. Protopanaxadiol alleviates neuropathic pain by spinal microglial dynorphin A expression following glucocorticoid receptor activation. Br J Pharmacol. 2021 Aug;178(15):2976-2997. doi: 10.1111/bph.15471. Epub 2021 May 4. PMID: 33786848.
In vitro protocol:
1. Berg KA, Rowan MP, Gupta A, Sanchez TA, Silva M, Gomes I, McGuire BA, Portoghese PS, Hargreaves KM, Devi LA, Clarke WP. Allosteric interactions between δ and κ opioid receptors in peripheral sensory neurons. Mol Pharmacol. 2012 Feb;81(2):264-72. doi: 10.1124/mol.111.072702. Epub 2011 Nov 9. PMID: 22072818; PMCID: PMC3263945. 2. Reeves PJ, Callewaert N, Contreras R, Khorana HG. Structure and function in rhodopsin: high-level expression of rhodopsin with restricted and homogeneous N-glycosylation by a tetracycline-inducible N-acetylglucosaminyltransferase I-negative HEK293S stable mammalian cell line. Proc Natl Acad Sci U S A. 2002 Oct 15;99(21):13419-24. doi: 10.1073/pnas.212519299. Epub 2002 Oct 7. PMID: 12370423; PMCID: PMC129688.
In vivo protocol:
1. Marchette RCN, Gregory-Flores A, Tunstall BJ, Carlson ER, Jackson SN, Sulima A, Rice KC, Koob GF, Vendruscolo LF. κ-Opioid receptor antagonism reverses heroin withdrawal-induced hyperalgesia in male and female rats. Neurobiol Stress. 2021 Apr 14;14:100325. doi: 10.1016/j.ynstr.2021.100325. PMID: 33997152; PMCID: PMC8095052. 2. Shoaib RM, Ahmad KA, Wang YX. Protopanaxadiol alleviates neuropathic pain by spinal microglial dynorphin A expression following glucocorticoid receptor activation. Br J Pharmacol. 2021 Aug;178(15):2976-2997. doi: 10.1111/bph.15471. Epub 2021 May 4. PMID: 33786848.
1: Jones RM, Portoghese PS. 5'-Guanidinonaltrindole, a highly selective and potent kappa-opioid receptor antagonist. Eur J Pharmacol. 2000 May 12;396(1):49-52. PubMed PMID: 10822054.