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B112

Sigma-Aldrich

(±)-Bay K8644

calcium channel agonist

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H15F3N2O4
CAS Number:
71145-03-4
Molecular Weight:
356.30
MDL number:
MFCD00036697
UNSPSC Code:
12352202
PubChem Substance ID:
24277825
NACRES:
NA.77

Quality Level

100

assay

≥97.5% (HPLC)

form

powder

color

yellow to dark yellow

mp

168-170  °C

solubility

DMSO: 20 mg/mL
methanol and ethanol: 63 mg/mL
H2O: insoluble

storage temp.

2-8°C

SMILES string

CC1=C(C(OC)=O)C(C2=CC=CC=C2C(F)(F)F)C([N+]([O-])=O)=C(C)N1

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

InChI key

ZFLWDHHVRRZMEI-UHFFFAOYSA-N

Gene Information

rat ... Cacna1c(24239)

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Application

(±)-Bay K8644 has been used as an agonist for voltage sensitive calcium channels (VSCCs) in interneurons, L-type calcium channel (LTCC) in human embryonic kidney 293 cells and viscerofugal neurons.

Biochem/physiol Actions

(±)-Bay K8644 is a 1,4-dihydropyridine (DHP) derivative and an agonist for L-type Ca2+ channels. However, it′s enantiomers (-)-BAY k8644 and (+)-BAY k8644 have opposing functionality with respect to Ca2+ channels as high-potency agonist and low-potency antagonist, respectively. (±)-Bay K8644 increases influx of Ca2+ specifically at voltage-gated calcium channels. It constricts blood vessels and heart contraction.
Increases influx of Ca2+ specifically at voltage-gated calcium channels.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Opposing actions of Bay K 8644 enantiomers on calcium current, prolactin secretion, and synthesis in pituitary cells
Enyeart JJ, et al.
Molecular Endocrinology, 4(5), 727-735 (1990)
CaV1.2 channelopathic mutations evoke diverse pathophysiological mechanisms.
Bamgboye, et al.
The Journal of General Physiology, 154 (2023)
Diego Santos de Souza et al.
European journal of pharmacology, 859, 172488-172488 (2019-06-25)
Cardiac arrhythmias are among the most important pathologies that lead to sudden death. The discovery of new therapeutic options against arrhythmias with low adverse effects is of paramount importance. Farnesol is found in essential oils with antioxidant, anti-inflammatory and cardioprotective
The calcium channel agonist BAY k 8644 reduces ethanol intake and preference in alcohol-preferring AA rats
de Beun R, et al.
Psychopharmacology, 127(1-2), 302-310 (1996)
Spectrum of Cav1. 4 dysfunction in congenital stationary night blindness type 2
Burtscher V, et al.
Biochimica et Biophysica Acta, 1838(8), 2053-2065 (2014)
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