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N156

Sigma-Aldrich

Naltriben methanesulfonate hydrate

≥98% (HPLC), solid

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Synonym(s):
NTB hydrate
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

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Profiling molecular factors associated with pyknosis and developmental arrest induced by an opioid receptor antagonist and dihydroartemisinin in Plasmodium falciparum
Asahi H, et al.
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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
Liliana Matos et al.
Orphanet journal of rare diseases, 9, 180-180 (2014-12-11)
Mutations affecting RNA splicing represent more than 20% of the mutant alleles in Sanfilippo syndrome type C, a rare lysosomal storage disorder that causes severe neurodegeneration. Many of these mutations are localized in the conserved donor or acceptor splice sites
Inhibitory effect of deltorphin-II on development of malaria in Plasmodium berghei-infected mice
Ajitbhai GA, et al.
MalariaWorld journal, 6, 3-3 (2017)
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Human mutation, 40(8), 1084-1100 (2019-06-23)
Mucopolysaccharidosis type IIIC (MPSIIIC) is a severe, rare autosomal recessive disorder caused by variants in the heparan-α-glucosaminide N-acetyltransferase (HGSNAT) gene which result in lysosomal accumulation of heparan sulfate. We analyzed clinical presentation, molecular defects and their haplotype context in 78
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