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Z0127

Sigma-Aldrich

Zatebradine hydrochloride

≥98% (HPLC), powder

Synonym(s):

7,8-Dimethoxy-3-[3-[-N-[2-(3,4 dimethoxyphenyl)ethyl]-N-methylamino]propyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one hydrochloride, UL-FS49

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About This Item

Empirical Formula (Hill Notation):
C26H37ClN2O5
CAS Number:
91940-87-3
Molecular Weight:
493.04
MDL number:
MFCD06798356
UNSPSC Code:
12352200
PubChem Substance ID:
24724672
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white

solubility

H2O: >10 mg/mL

originator

Boehringer Ingelheim

storage temp.

2-8°C

SMILES string

Cl[H].COc1ccc(CCN(C)CCCN2CCc3cc(OC)c(OC)cc3CC2=O)cc1OC

InChI

1S/C26H36N2O5.ClH/c1-27(13-9-19-7-8-22(30-2)23(15-19)31-3)11-6-12-28-14-10-20-16-24(32-4)25(33-5)17-21(20)18-26(28)29;/h7-8,15-17H,6,9-14,18H2,1-5H3;1H

InChI key

ZRNKXJHEQKMWCH-UHFFFAOYSA-N

Application

Zatebradine hydrochloride has been used:
  • as an If blocker to study its effects on cardiomyocyte clusters (CMCs)
  • as a hyperpolarization-activated and cyclic nucleotide-gated (HCN) channel inhibitor to study its effects on viability of degenerating rod or cone photoreceptors in mice
  • as a bradycardiac agent to study its effects on tachycardia and elevated temperature in fish

Biochem/physiol Actions

Zatebradine is a bradycardiac agent.
HCN channel blocker: blocker of neuronal Ih, related cardiac If channels and ATP-sensitive Kir channels.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Boehringer Ingelheim. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

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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Jordi Altimiras et al.
The Journal of experimental biology, 207(Pt 2), 195-201 (2003-12-12)
Intrinsic regulation of the heart in teleosts is partly driven by central venous pressure, which exerts a modulatory role on stroke volume according to the well-known Frank-Starling mechanism. Although this mechanism is well understood from heart perfusion studies, less is
Arun Sridhar et al.
American journal of physiology. Heart and circulatory physiology, 291(5), H2192-H2198 (2006-06-13)
Hypertension is a common cause of heart failure, and ventricular arrhythmias are a major cause of death in heart failure. The spontaneous hypertension heart failure (SHHF) rat model was used to study altered ventricular electrophysiology in hypertension and heart failure.
Annette Hellbach et al.
Journal of experimental zoology. Part A, Ecological genetics and physiology, 315(8), 476-486 (2011-07-20)
Hyperpolarization-activated, cyclic nucleotide-gated (HCN) channels generate the rhythmic beating of mammalian hearts. We identified an HCN homolog in the colonial ascidian Botryllus schlosseri, a nonvertebrate chordate which possesses a tubular heart that beats bidirectionally. Contractions initiate at one end of
Elevated temperature, per se, does not limit the ability of rainbow trout to increase stroke volume
Gamperl A K, et al.
Journal of Thermal Biology, 36(1), 7-14 (2011)
M De Pauw et al.
Basic research in cardiology, 99(5), 360-371 (2004-09-01)
Myocardial contractility is regulated by adrenergic stimulation, the strength-length relationship and the force-frequency relationship or Bowditch effect. The latter mechanism was clearly demonstrated in muscle strips, in the isolated heart as well as in in-vivo experiments. The aim of this
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