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C5493

Sigma-Aldrich

CyPPA

≥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
MDL number:
MFCD01550586
UNSPSC Code:
12352200
PubChem Substance ID:
329775087
NACRES:
NA.77

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 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
GHS07

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

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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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
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)
Miao Zhang et al.
Nature communications, 3, 1021-1021 (2012-08-30)
Small- and intermediate-conductance Ca(2+)-activated potassium channels, activated by Ca(2+)-bound calmodulin, have an important role in regulating membrane excitability. These channels are also linked to clinical abnormalities. A tremendous amount of effort has been devoted to developing small molecule compounds targeting
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
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