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Merck

C5493

Sigma-Aldrich

CyPPA

≥98% (HPLC), solid

Sinónimos:

Cyclohexyl-[2-(3,5-dimethyl-pyrazol-1-yl)-6-methyl-pyrimidin-4-yl]-amine

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About This Item

Fórmula empírica (notación de Hill):
C16H23N5
Número de CAS:
Peso molecular:
285.39
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: >10 mg/mL
H2O: <2 mg/mL

storage temp.

2-8°C

SMILES string

Cc1cc(NC2CCCCC2)nc(n1)-n3nc(C)cc3C

InChI

1S/C16H23N5/c1-11-10-15(18-14-7-5-4-6-8-14)19-16(17-11)21-13(3)9-12(2)20-21/h9-10,14H,4-8H2,1-3H3,(H,17,18,19)

InChI key

USEMRPYUFJNFQN-UHFFFAOYSA-N

Application

CyPPA has been used:
  • to test its inhibitory functionality on melanogenesis
  • as an activator of small conductance potassium channel-3 (SK3) in mesenteric artery segments
  • in the activation of calcium-activated potassium (SK) channels in murine hippocampal neurons HT-22 cells

Biochem/physiol Actions

CyPPA is a positive modulator of small conductance Ca2+-activated K+ channels; selective for SK3 and SK2. CyPPA is a first subtype selective SK channel positive modulator with an EC50 of 5.6 μM and 14 μM, efficacy 90% and 71% for hSK3 and hSK2, respectively. CyPPA is a tool for distinguishing SK2 and SK3 from SK1 and IK; no other agents distinguish these channels.

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Amita Shrestha et al.
Developmental neuroscience, 42(1), 59-71 (2020-06-25)
N-methyl-D-aspartate receptor (NMDAR) modulates the structural plasticity of dendritic spines by impacting cytoskeletal organization and kinase signaling. In the developing nervous system, activation of NMDAR is pertinent for neuronal migration, neurite differentiation, and cellular organization. Given that small conductance potassium
SK channel activation modulates mitochondrial respiration and attenuates neuronal HT-22 cell damage induced by H2O2
Richter M, et al.
Neurochemistry International, 81, 63-75 (2015)
The ion channel activator CyPPA inhibits melanogenesis via the GSK3betabeta-catenin pathway
Noh TK, et al.
Chemico-Biological Interactions, 300, 1-7 (2019)
Sulie L Chang et al.
Journal of neuroimmune pharmacology : the official journal of the Society on NeuroImmune Pharmacology (2018-07-11)
Ethanol (EtOH), the main ingredient in alcoholic beverages, is well known for its behavioral, physiological, and immunosuppressive effects. There is evidence that EtOH acts through protein targets to exert its physiological effects; however, the mechanisms underlying EtOH's effects on inflammatory
Hui Ye et al.
Science advances, 10(28), eadi4746-eadi4746 (2024-07-12)
Oxysterols are metabolites of cholesterol that regulate cholesterol homeostasis. Among these, the most abundant oxysterol is 27-hydroxycholesterol (27HC), which can cross the blood-brain barrier. Because 27HC functions as an endogenous selective estrogen receptor modulator, we hypothesize that 27HC binds to

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