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C2615

Sigma-Aldrich

Chromanol 293B

≥98% (HPLC), powder

Synonym(s):

trans-N-[6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl]-N-methyl-ethanesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C15H20N2O4S
CAS Number:
163163-23-3
Molecular Weight:
324.40
MDL number:
MFCD06798368
UNSPSC Code:
12352200
PubChem Substance ID:
329775012
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white

solubility

DMSO: 18 mg/mL

storage temp.

−20°C

SMILES string

CCS(=O)(=O)N(C)[C@@H]1[C@@H](O)C(C)(C)Oc2ccc(cc12)C#N

InChI

1S/C15H20N2O4S/c1-5-22(19,20)17(4)13-11-8-10(9-16)6-7-12(11)21-15(2,3)14(13)18/h6-8,13-14,18H,5H2,1-4H3/t13-,14+/m0/s1

InChI key

HVSJHHXUORMCGK-UONOGXRCSA-N

General description

Chromanol 293B enantiomer is a potent inhibitor of potassium channel protein (KvLQT1). In human atrial myocytes, chromanol 293B inhibits repolarization potassium currents. Chromanol 293B improves glucose-stimulated insulin secretion (GSIS) in pancreas by modulating potassium voltage-gated channel (KCNQ1).

Application

Chromanol 293B has been used in the inhibition of calcium and cyclic adenosine monophosphate (cAMP)-activated potassium channels in human epithelial cell lines. Chromanol 293B has been used in patch-clamp electrophysiology studies in cardiomyocytes.

Biochem/physiol Actions

Blocker of the slow delayed rectifier K+ current via KCNQ1 channels

Features and Benefits

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

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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A Varro et al.
The Journal of physiology, 523 Pt 1, 67-81 (2000-02-16)
1. The relative contributions of the rapid and slow components of the delayed rectifier potassium current (IKr and IKs, respectively) to dog cardiac action potential configuration were compared in ventricular myocytes and in multicellular right ventricular papillary muscle and Purkinje
CFTR-mediated anion secretion across intestinal epithelium-like Caco-2 monolayer under PTH stimulation is dependent on intermediate conductance K+ channels
Jantarajit W, et al.
American Journal of Physiology. Cell Physiology, 313(1), C118-C129 (2017)
Stereoselective interactions of the enantiomers of chromanol 293B with human voltage-gated potassium channels
Yang IC, et al.
Journal of Pharmacology and Experimental Therapeutics, 294(3), 955-962 (2000)
J E Matos et al.
Acta physiologica (Oxford, England), 189(3), 251-258 (2007-02-20)
Colonic crypts are the site of Cl- secretion. Basolateral K+ channels provide the driving force for luminal cystic fibrosis transmembrane regulator-mediated Cl- exit. Relevant colonic epithelial K+ channels are the intermediate conductance Ca2+-activated K(Ca)3.1 (SK4) channel and the cAMP-activated K(V)7.1
Chromanol 293B, an inhibitor of KCNQ1 channels, enhances glucose-stimulated insulin secretion and increases glucagon-like peptide-1 level in mice
Liu L, et al.
Islets, 6(4), e962386-e962386 (2014)
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