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Home > Products > Specialty & Industrial Chemicals > Specialty Chemicals > 2-[2-[4-(4-Nitrobenzyloxy)phenyl]ethyl]isothioureamesylate
2-[2-[4-(4-Nitrobenzyloxy)phenyl]ethyl]isothioureamesylate structure, CAS 182004-65-5

2-[2-[4-(4-Nitrobenzyloxy)phenyl]ethyl]isothioureamesylate

CAS Number182004-65-5

SynonymsHMS3267H09; KB-R7943; MFCD00237019; 2-{4-[(4-Nitrobenzyl)oxy]phenyl}ethyl carbamimidothioate methanesulfonate (1:1); Carbamimidothioic Acid 4-[(4-Nitrobenzyl)oxy]phenethyl Ester Methanesulfonate; 4-[(4-Nitrobenzyl)oxy]phenethyl Carbamimidothioate Methanesulfonate; Carbamimidothioic acid, 2-[4-[(4-nitrophenyl)methoxy]phenyl]ethyl ester, methanesulfonate (1:1); KB-R7943 (mesylate)

Molecular FormulaC17H21N3O6S2

Molecular Weight331.39 (free base basis)

Purity≥98 (HPLC)%

Density

Boiling Point534.6ºC at 760mmHg

Melting Point

Flash Point

Appearancecrystalline solid

EINECS

MSDSChineseEnglish

Symbol

Signal Word

Cat. No.: 2A-9080556 Purity: ≥98 (HPLC)%
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Quality Control of [ 182004-65-5 ] Purity: ≥98 (HPLC)% SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number182004-65-5
Catalog No.2A-9080556
Chinese NameS-[4-[(4-硝基苄基)氧代]苯乙基]异硫脲甲磺酸盐
SynonymsHMS3267H09; KB-R7943; MFCD00237019; 2-{4-[(4-Nitrobenzyl)oxy]phenyl}ethyl carbamimidothioate methanesulfonate (1:1); Carbamimidothioic Acid 4-[(4-Nitrobenzyl)oxy]phenethyl Ester Methanesulfonate; 4-[(4-Nitrobenzyl)oxy]phenethyl Carbamimidothioate Methanesulfonate; Carbamimidothioic acid, 2-[4-[(4-nitrophenyl)methoxy]phenyl]ethyl ester, methanesulfonate (1:1); KB-R7943 (mesylate)
Molecular FormulaC17H21N3O6S2
Molecular Weight331.39 (free base basis)
Purity≥98 (HPLC)
Boiling Point534.6ºC at 760mmHg
Appearancecrystalline solid
Storage Condition2-8°C
ApplicationKB-R7943 mesylate is a Na+/Ca2+ exchanger (NCXrev) reverse inhibitor with an IC50 of 5.7±2.1 µM.
MDL NumberMFCD00952138
SMILES[S](=O)(=O)(O)C.S(CCc1ccc(cc1)OCc2ccc(cc2)[N+](=O)[O-])\C(=N\[H])\N
InChI1S/C16H17N3O3S.CH4O3S/c17-16(18)23-10-9-12-3-7-15(8-4-12)22-11-13-1-5-14(6-2-13)19(20)21;1-5(2,3)4/h1-8H,9-11H2,(H3,17,18);1H3,(H,2,3,4)
InChI KeyWGIKEBHIKKWJLG-UHFFFAOYSA-N
NACRES CodeNA.77
UNSPSC12352200
MSDSmsds/80556_1_182004_65_5.pdf
BioactivityKB-R7943 mesylate is a widely used inhibitor of the reverse Na+/Ca2+ exchanger (NCXrev) with IC50 of 5.7±2.1 µM. Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Na+/Ca2+ Exchanger Research Areas >> Others Target IC50: 5.7±2.1 µM (Na+/Ca2+ exchanger)[1] In Vitro KB-R7943 mesylate blocks NMDAR-mediated ion currents, and inhibits NMDA-induced increase in cytosolic Ca2+ with IC50=13.4±3.6 µM but accelerates calcium deregulation and mitochondrial depolarization in glutamate-treated neurons. KB-R7943 depolarizes mitochondria in a Ca2+-independent manner. KB-R7943 inhibits 2,4-dinitrophenol-stimulated respiration of cultured neurons with IC50=11.4±2.4 µM. In addition to NCXrev, KB-R7943 dose-dependently and reversibly blocked ion currents elicited by NMDA. KB-R7943 dose-dependently inhibits NMDA-induced increases in [Ca2+]c with IC50=13.4±3.6 µM confirming the inhibition of NMDA receptors observed in electrophysiological experiments[1]. wtRyR1-HEK 293 pretreated with KB-R7943 (10 μM, 10 min) dissolved in the bulk perfusion exhibited significantly attenuated responses to caffeine. In this regard, KB-R7943 produced more pronounced inhibition of caffeine-induced Ca2+ release elicited by 1 mM compared with 0.5 and 0.75 mM (60 versus 58 versus 37%, p<0.05, respectively)[2]. KB-R7943 inhibits both IhERG and native IKr rapidly on membrane depolarization with IC50 values of ~89 and ~120 nM, respectively, for current tails at −40 mV following depolarizing voltage commands to +20 mV. IhERG inhibition by KB-R7943 exhibits both time- and voltage-dependence but shows no preference for inactivated over activated channels[3]. Cell Assay EK 293 cells stably expressing the wtRyR1 (wtRyR1-HEK 293) are maintained in Dulbecco's modified Eagle's medium supplemented with 2 mM glutamine, 100 μg/mL streptomycin, 100 U/mL penicillin, 1 mM sodium pyruvate, and 10% fetal bovine serum at 37°C under 5% CO2. wtRyR1-HEK 293 cells are loaded with 5 μM Fluo-4 acetoxymethyl ester at 37°C for 30 min to measure Ca2+ transients in an imaging buffer consisting of 140 mM NaCl, 5 mM KCl, 2 mM MgCl2, 2 mM CaCl2, 10 mM HEPES, and 10 mM glucose, pH 7.4, supplemented with 0.05% bovine serum albumin. The cells are washed three times with imaging buffer and additionally incubated for 20 min at room temperature. Dye-loaded cells are washed three times with imaging buffer and imaged with a charge-coupled device camera with a 40× objective lens attached to an IX-71 microscope. The sequence of images is captured and monitored using EasyRatioPro. Caffeine dissolved in the imaging buffer is focally applied for 15 s using AutoMate Scientific. KB-R7943 is dissolved in the imaging buffer, and wtRyR1-HEK 293 cells are incubated for 10 min before the application of caffeine[2]. References [1]. Brustovetsky T, et al. KB-R7943, an inhibitor of the reverse Na+ /Ca2+ exchanger, blocks N-methyl-D-aspartate receptor and inhibits mitochondrial complex I. Br J Pharmacol. 2011 Jan;162(1):255-70. [2]. Barrientos G, et al. The Na+/Ca2+ exchange inhibitor 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate(KB-R7943) also blocks ryanodine receptors type 1 (RyR1) and type 2 (RyR2) channels. Mol Pharmacol. 2009 Sep;76(3):560-8. [3]. Cheng H, et al. High potency inhibition of hERG potassium channels by the sodium-calcium exchange inhibitor KB-R7943. Br J Pharmacol. 2012 Apr;165(7):2260-73. Chemical & Physical Properties Boiling Point 534.6ºC at 760mmHg Molecular Formula C17H21N3O6S2 Molecular Weight 427.495 Flash Point 277.1ºC Exact Mass 427.087189 PSA 192.97000 LogP 5.25100 Vapour Pressure 1.67E-11mmHg at 25°C InChIKey WGIKEBHIKKWJLG-UHFFFAOYSA-N SMILES CS(=O)(=O)O.N=C(N)SCCc1ccc(OCc2ccc([N+](=O)[O-])cc2)cc1 Storage condition 2-8°C
Use ofProperties Name methanesulfonic acid,2-[4-[(4-nitrophenyl)methoxy]phenyl]ethyl carbamimidothioate Synonym More Synonyms Related Catalog Signaling Pathways >> Membrane Transporter/Ion Channel >> Na+/Ca2+ Exchanger Research Areas >> Others References [1]. Brustovetsky T, et al. KB-R7943, an inhibitor of the reverse Na+ /Ca2+ exchanger, blocks N-methyl-D-aspartate receptor and inhibits mitochondrial complex I. Br J Pharmacol. 2011 Jan;162(1):255-70. [2]. Barrientos G, et al. The Na+/Ca2+ exchange inhibitor 2-(2-(4-(4-nitrobenzyloxy)phenyl)ethyl)isothiourea methanesulfonate(KB-R7943) also blocks ryanodine receptors type 1 (RyR1) and type 2 (RyR2) channels. Mol Pharmacol. 2009 Sep;76(3):560-8. [3]. Cheng H, et al. High potency inhibition of hERG potassium channels by the sodium-calcium exchange inhibitor KB-R7943. Br J Pharmacol. 2012 Apr;165(7):2260-73. Chemical & Physical Properties Molecular Formula C17H21N3O6S2 Exact Mass 427.087189 PSA 192.97000 LogP 5.25100 InChIKey WGIKEBHIKKWJLG-UHFFFAOYSA-N
Transport InfoProduct name: Purity: 98.0%
MSDS Transport InfoModule 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified
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