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B8312

Sigma-Aldrich

BNTX maleate salt hydrate

≥98% (HPLC)

Synonym(s):

7(E)-Benzylidenenaltrexone maleate salt hydrate, BNTX-7 maleate salt hydrate, Morphinan-6-one,17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-7-(phenylmethylene)-,(5a,7E)- maleate salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C31H31NO8 · xH2O
Molecular Weight:
545.58 (anhydrous basis)
MDL number:
MFCD12912399
UNSPSC Code:
12352200
PubChem Substance ID:
329773306
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

yellow

solubility

DMSO: >20 mg/mL

storage temp.

−20°C

SMILES string

O.OC(=O)\C=C/C(O)=O.Oc1ccc2C[C@H]3N(CC[C@@]45[C@@H](Oc1c24)C(=O)\C(C[C@@]35O)=C\c6ccccc6)CC7CC7

InChI

1S/C27H27NO4.C4H4O4.H2O/c29-20-9-8-18-13-21-27(31)14-19(12-16-4-2-1-3-5-16)23(30)25-26(27,22(18)24(20)32-25)10-11-28(21)15-17-6-7-17;5-3(6)1-2-4(7)8;/h1-5,8-9,12,17,21,25,29,31H,6-7,10-11,13-15H2;1-2H,(H,5,6)(H,7,8);1H2/b19-12+;2-1-;/t21-,25+,26+,27-;;/m1../s1

InChI key

AGUNLJBLOJAUKM-ZKJXOIBSSA-N

Application

BNTX, a selective nonpeptide σ1 opioid receptor (DOR1) antagonist, is used in σ opioid receptor research to help differentiate and characterized the function and role of the σ1 opioid receptor versus other σ opioid receptor subtypes. BNTX was used to help define the role of σ1 opioid receptors in neurological processes such as anxiety. It was used to help define the role of σ opioid receptors in myocardial infarct development and size.

Biochem/physiol Actions

BNTX is a selective nonpeptide δ1 opioid receptor antagonist. It antagonizes the effect of D-Pen2,5-enkephalin (a δ1 agonist 4-6 fold, but did not affect the activity of δ2 or μ agonists.<<<107>>> BNTX is used to discriminate among opioid receptor subtypes in effects such as alcohol and drug dependence. It binds 100× more tightly to δ1 than to δ2 receptors. In the tail-flick assay, antinocieceptive ED50 = 646.4 pmol/mouse.

Features and Benefits

This compound is featured on the Opioid Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H319,H400

Hazard Classifications

Aquatic Acute 1 - Eye Irrit. 2

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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Yoshinori Miyata et al.
Bioorganic & medicinal chemistry letters, 21(16), 4710-4712 (2011-07-19)
We evaluated antimalarial and/or chloroquine-resistance reversing effects of five opioid receptor antagonists. Although none of the evaluated compounds showed antimalarial effects, some of them, especially the δ(1) receptor antagonist, 7-benzylidenenaltrexone (BNTX) exhibited potent chloroquine-resistance reversing effects in Plasmodium chabaudi.
Azusa Sugiyama et al.
Neuropharmacology, 79, 314-320 (2013-12-18)
Recently, we reported that the δ opioid receptor (DOR) agonist KNT-127 produces anxiolytic-like effects in behaving rats. Here, we report on the roles of DOR subtypes ( DOR(1) and DOR(2)) play in mediating KNT-127-induced anxiolytic-like effects. Pretreatment with the DOR(2)-selective
Garrett J Gross et al.
Journal of cardiovascular pharmacology, 59(2), 194-197 (2011-12-02)
Eribis peptide 94 (EP 94) is a novel enkephalin derivative that binds with high potency to μ and δ opioid receptors with less affinity for the κ opioid receptor. This compound has recently been shown to produce an acute reduction
So Young Kim et al.
Oncotarget, 8(37), 61057-61071 (2017-10-06)
Tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) is a potential biological anticancer agent. However, a wide range of human primary cancers, including pancreatic cancer, display resistance to apoptosis induction by TRAIL. Therefore, this resistance needs to be overcome to allow TRAIL

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