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B133

(S)-(−)-Bay K8644

≥98% (HPLC), Ca2+ channel activator, solid

Synonym(s):

S-(−)-1,4-Dihydro-2,6-dimethyl-5-nitro-4-[2-(trifluoromethyl)phenyl]-3-pyridinecarboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C16H15F3N2O4
CAS Number:
98625-26-4
Molecular Weight:
356.30
UNSPSC Code:
12352200
PubChem Substance ID:
24891582
NACRES:
NA.77
MDL number:
MFCD00153769
Assay:
≥98% (HPLC)
Form:
solid
Quality level:
100
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Product Name

(S)-(−)-Bay K8644, ≥98% (HPLC), solid

Quality Level

100

assay

≥98% (HPLC)

form

solid

color

yellow

solubility

H2O: slightly soluble, ethanol: soluble (Organic solutions are stable for at least 20 days at RT.)

storage temp.

2-8°C

SMILES string

COC(=O)C1=C(C)NC(C)=C([C@H]1c2ccccc2C(F)(F)F)[N+]([O-])=O

InChI

1S/C16H15F3N2O4/c1-8-12(15(22)25-3)13(14(21(23)24)9(2)20-8)10-6-4-5-7-11(10)16(17,18)19/h4-7,13,20H,1-3H3/t13-/m0/s1

InChI key

ZFLWDHHVRRZMEI-ZDUSSCGKSA-N

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290), Adora2a(25369)

General description

(S)-(-)-Bay K8644, a dihydropyridine compound is a Ca2+ channel activator. It is an enantiomer of Bay K 8644.

Application

(S)-(-)-Bay K8644 has been used as a L-type calcium channel (LTCC) agonist in the suprachiasmatic nucleus (SCN) slices. It has also been used as a LTCC agonist to induce arrhythmia in rats.

Biochem/physiol Actions

(S)-(-)-Bay K8644 enhances Ca2+ current, whereas the (+)-Bay K 8644 is a weak Ca2+ channel antagonist. Bay K 8644 is lipophilic and it effectively scavenges superoxide anions.

Features and Benefits

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

Legal Information

Manufactured and sold with the permission of Bayer AG.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000238241
0000238241
0000151641
0000151641
0000148220

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J J Enyeart et al.
Molecular endocrinology (Baltimore, Md.), 4(5), 727-735 (1990-05-01)
Dihydropyridine (DHP) Ca2+ channel modulators were used to explore the relationship between voltage-gated Ca2+ channels and PRL secretion, synthesis, and mRNA in PRL-secreting pituitary cells. Optical isomers of the Ca2+ channel agonist Bay K 8644 produced stereospecific and opposing effects
Joshua P Whitt et al.
The Journal of general physiology, 150(2), 259-275 (2017-12-15)
Large conductance K+ (BK) channels are expressed widely in neurons, where their activation is regulated by membrane depolarization and intracellular Ca2+ (Ca2+i). To enable this regulation, BK channels functionally couple to both voltage-gated Ca2+ channels (VGCCs) and channels mediating Ca2+
Paula Clancy et al.
Journal of atherosclerosis and thrombosis, 23(7), 773-791 (2016-03-08)
Matrix metalloproteinases (MMPs), angiotensin II (AII) and its receptors are implicated in atherosclerotic plaque instability, however the roles of the two receptor subtypes, ATR1 and ATR2, in MMP regulation remain uncertain. In this study, we investigated the effect of ATR1
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