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C5493

CyPPA

Name: CyPPA
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₁₆H₂₃N₅

CAS Number:

73029-73-9

Molecular Weight:

285.39

NACRES:

NA.77

PubChem Substance ID:

329775087

UNSPSC Code:

12352200

MDL number:

MFCD01550586

Assay:

≥98% (HPLC)

Form:

solid

Quality level:

100

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Quality Level

100

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 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

GHS07

signalword

Warning

hcodes

H315,H319,H335,H413

pcodes

P273 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

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

Regulatory Information

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Positive Modulation of SK Channel Impedes Neuron-Specific Cytoskeletal Organization and Maturation.

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)

Ethanol's Effects on Transient Receptor Potential Channel Expression in Brain Microvascular Endothelial Cells.

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

27-Hydroxycholesterol acts on estrogen receptor α expressed by POMC neurons in the arcuate nucleus to modulate feeding behavior.

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

Diabetes-induced colonic slow transit mediated by the up-regulation of PDGFRα+ cells/SK3 in streptozotocin-induced diabetic mice.

N-N Song et al.

Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society (2018-03-10)

A major complication related to gastrointestinal (GI) symptoms in diabetic patients is chronic constipation. Constipation has serious negative impacts on quality of life; however, without a comprehensive understanding of the disease, currently available treatments cannot provide a cure. Platelet-derived growth

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Global Trade Item Number

SKU	GTIN
C5493-25MG	04061832574196
C5493-5MG	04061832574202

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