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N156

Sigma-Aldrich

Naltriben methanesulfonate hydrate

≥98% (HPLC), solid

Synonym(s):

NTB hydrate

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About This Item

Empirical Formula (Hill Notation):
C26H25NO4 · CH4O3S · xH2O
CAS Number:
1309441-44-8
Molecular Weight:
511.59 (anhydrous basis)
MDL number:
MFCD11046015
UNSPSC Code:
12352200
PubChem Substance ID:
24278045
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

solid

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

color

off-white

solubility

DMSO: 14 mg/mL at ~60 °C

storage temp.

−20°C

SMILES string

O.CS(O)(=O)=O.Oc1ccc2C[C@H]3N(CC[C@@]45[C@@H](Oc1c24)c6oc7ccccc7c6C[C@@]35O)CC8CC8

InChI

1S/C26H25NO4.CH4O3S.H2O/c28-18-8-7-15-11-20-26(29)12-17-16-3-1-2-4-19(16)30-22(17)24-25(26,21(15)23(18)31-24)9-10-27(20)13-14-5-6-14;1-5(2,3)4;/h1-4,7-8,14,20,24,28-29H,5-6,9-13H2;1H3,(H,2,3,4);1H2/t20-,24+,25+,26-;;/m1../s1

InChI key

VAGWKZSGWSRENH-HIAJFTJMSA-N

Application

Naltriben methanesulfonate hydrate has been used in the assessment of parasite growth and evaluation of growth inhibition. It has also been used to understand the action of deltorphin-II in exhibiting its antimalarial effect.

Biochem/physiol Actions

Naltriben methanesulfonate is a highly selective δ2 opioid receptor antagonist. The relative ability of the delta antagonists benzylidenenaltrexone and naltriben to inhibit DPDPE-stimulated [35S]GTPgammaS binding suggests that the opioid receptor is of the delta-2 subtype. Ligand binding assays demonstrates biphasic binding of the antagonist to the single receptor type. [35S]GTPgammaS binding is also stimulated by [D-Ser2,Leu5,Thr6]enkephalin > deltorphin II = DPDPE = etorphine > levallorphan = diprenorphine = nalorphine = naltrindole.

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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Inhibitory effect of deltorphin-II on development of malaria in Plasmodium berghei-infected mice
Ajitbhai GA, et al.
MalariaWorld journal, 6, 3-3 (2017)
A E Takemori et al.
Life sciences, 50(20), 1491-1495 (1992-01-01)
The pharmacological profile of naltrindole (NTI) and three of its analogues, N-methyl-NTI (N-Me-NTI), oxymorphindole (OMI) and naltriben (NTB) were studied in antinociceptive assays. The compounds were found to have agonist activities that appear to be mediated mainly by kappa opioid
Profiling molecular factors associated with pyknosis and developmental arrest induced by an opioid receptor antagonist and dihydroartemisinin in Plasmodium falciparum
Asahi H, et al.
Testing, 12(9), e0184874-e0184874 (2017)
Tae-Jin Kim et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 6(4), 1801290-1801290 (2019-03-05)
The dynamic regulation of signal transduction at plasma membrane microdomains remains poorly understood due to limitations in current experimental approaches. Genetically encoded biosensors based on fluorescent resonance energy transfer (FRET) can provide high spatiotemporal resolution for imaging cell signaling networks.
Y Miyamoto et al.
The Journal of pharmacology and experimental therapeutics, 264(3), 1141-1145 (1993-03-01)
The possible involvement of delta 2 opioid receptors in the development of morphine dependence was investigated using selective delta 2 receptor antagonists, naltriben (NTB) and naltrindole 5'-isothiocyanate (5'-NTII). The degree of morphine dependence was estimated by the ED50 values of
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