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SML2354

Sigma-Aldrich

HMR-1556

≥98% (HPLC)

Synonym(s):

(3R,4S)-(+)-N-[3-Hydroxy-2,2-dimethyl-6-(4,4,4,-trifluorobutoxy)chroman-4-yl]-N-methylmethanesulfonamide, Chromanol HMR 1556, HMR 1556, HMR1556, N-[(3R,4S)-3,4-Dihydro-3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)-2H-1-benzopyran-4-yl]-N-methylmethanesulfonamide

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About This Item

Empirical Formula (Hill Notation):
C17H24F3NO5S
CAS Number:
223749-46-0
Molecular Weight:
411.44
MDL number:
MFCD12756323
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +2 to +3.5°, c = 0.1 in methanol

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CC1([C@@H]([C@H](C2=CC(OCCCC(F)(F)F)=CC=C2O1)N(C)S(C)(=O)=O)O)C

InChI

1S/C17H24F3NO5S/c1-16(2)15(22)14(21(3)27(4,23)24)12-10-11(6-7-13(12)26-16)25-9-5-8-17(18,19)20/h6-7,10,14-15,22H,5,8-9H2,1-4H3/t14-,15+/m0/s1

InChI key

SRZRLJWUQFIZRH-LSDHHAIUSA-N

Biochem/physiol Actions

HMR-1556 is a potent and selective blocker of the heteromeric KCNQ1-KCNE1 (KvLQT1-MinK) voltage-gated channel-mediated slowly activating K+ current (IKs IC50 = 120 nM in hKCNE1-transfected Xenopus oocytes; little or no inhibition of Herg, Kv1.3 (KCNA3), Kv1.5 (KCNA5), Kir2.1 (KCNJ2), HCN2 (BCNG2) current in respective oocyte transfectants). HMR-1556 is more potent than chromanol 293B (IKs IC50 = 34 nM and 2.1 μM, respectively; guinea pig ventricular myocytes), being inefficient against L-type Ca2+ channel or rapidly delayed & inward rectifier currents (IKr & IK1) in guinea pig ventricular myocytes, nor transient & sustained outward currents, I(to) & I(sus), in rat ventricular myocytes.

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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C Lerche et al.
British journal of pharmacology, 131(8), 1503-1506 (2001-01-05)
Slowly activating I:(Ks) (KCNQ1/MinK) channels were expressed in Xenopous: oocytes and their sensitivity to chromanols was compared to homomeric KCNQ1 channels. To elucidate the contribution of the ss-subunit MinK on chromanol block, a formerly described chromanol HMR 1556 and its
Jie Wu et al.
Scientific reports, 8(1), 3129-3129 (2018-02-17)
Congenital long QT syndrome (LQTS) caused by compound mutations is usually associated with more severe clinical phenotypes. We identified a LQTS family harboring three compound mutations in different genes (KCNQ1-R174C, hERG-E1039X and SCN5A-E428K). KCNQ1-R174C, hERG-E1039X and SCN5A-E428K mutations and/or relevant
Bence Hegyi et al.
Proceedings of the National Academy of Sciences of the United States of America, 115(13), E3036-E3044 (2018-03-14)
Heart failure (HF) following myocardial infarction (MI) is associated with high incidence of cardiac arrhythmias. Development of therapeutic strategy requires detailed understanding of electrophysiological remodeling. However, changes of ionic currents in ischemic HF remain incompletely understood, especially in translational large-animal
George P Thomas et al.
Journal of cardiovascular pharmacology, 41(1), 140-147 (2002-12-25)
The slowly activating delayed rectifier potassium current (IKs) contributes prominently to ventricular repolarization of the cardiac action potential. Development of a selective IKs blocker is important for the elucidation of the physiologic and pathophysiologic relevance of IKs and the development
H Gögelein et al.
Naunyn-Schmiedeberg's archives of pharmacology, 362(6), 480-488 (2001-01-04)
Chromanol HMR 1556 [(3R,4S)-(+)-N-[3-hydroxy-2,2-dimethyl-6-(4,4,4-trifluorobutoxy)chroman-4-yl]-N-methylmethanesulfonamide], a novel inhibitor of the slow component of the delayed outward current in heart muscle cells (IKs), has been characterized in several in-vitro systems. mRNA encoding for the human protein minK was injected into Xenopus oocytes
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