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SML2354

HMR-1556

Name: HMR-1556
Brand: SIGMA

≥98% (HPLC), KCNQ1-KCNE1 (KvLQT1-MinK) blocker, powder

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

NACRES:

NA.77

UNSPSC Code:

12352200

MDL number:

MFCD12756323

Assay:

≥98% (HPLC)

Form:

powder

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Product Name

HMR-1556, ≥98% (HPLC)

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

Related Categories

Bioactive Small Molecules

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.

Potent and selective blocker of the heteromeric KCNQ1-KCNE1 (KvLQT1-MinK) voltage-gated channel-mediated slowly activating K+ current (Iks).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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HMR 1556, a potent and selective blocker of slowly activating delayed rectifier potassium current.

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

Sympathetic Nervous Regulation of Calcium and Action Potential Alternans in the Intact Heart.

James Winter et al.

Frontiers in physiology, 9, 16-16 (2018-02-08)

Rationale: Arrhythmogenic cardiac alternans are thought to be an important determinant for the initiation of ventricular fibrillation. There is limited information on the effects of sympathetic nerve stimulation (SNS) on alternans in the intact heart and the conclusions of existing

Quantitative analysis of the Ca2+ -dependent regulation of delayed rectifier K+ current IKs in rabbit ventricular myocytes.

Daniel C Bartos et al.

The Journal of physiology, 595(7), 2253-2268 (2016-12-23)

[Ca2+ ]i enhanced rabbit ventricular slowly activating delayed rectifier K+ current (IKs ) by negatively shifting the voltage dependence of activation and slowing deactivation, similar to perfusion of isoproterenol. Rabbit ventricular rapidly activating delayed rectifier K+ current (IKr ) amplitude

Effects of the chromanol HMR 1556 on potassium currents in atrial myocytes.

Ralph F Bosch et al.

Naunyn-Schmiedeberg's archives of pharmacology, 367(3), 281-288 (2003-03-20)

The chromanol HMR 1556 is a potent blocker of KvLQT1/minK potassium channels expressed in Xenopus oocytes. The compound is therefore a new class III antiarrhythmic drug with a distinct mechanism of action. However, the effect of HMR 1556 on atrial

Inhibition of IKs channels by HMR 1556.

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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Global Trade Item Number

SKU	GTIN
SML2354-25MG	04061838526403
SML2354-5MG	04061838526410

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