IUPAC/Chemical Name
N-cyclohexyl-2-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylpyrimidin-4-amine
InChi Key
USEMRPYUFJNFQN-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CC1=CC(C)=NN1C2=NC(C)=CC(NC3CCCCC3)=N2
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
CyPPA is a positive modulator of hSK3 and hSK2, with EC50 values of 14 μM and 5.6 μM, repectively.
In vitro activity:
CyPPA treatment resulted in a significant concentration-dependent reduction in melanin content without significant cytotoxicity; treatment likewise resulted in a significant time-dependent reduction in tyrosinase (TYR) activity.
Reference: Chem Biol Interact. 2019 Feb 25;300:1-7. https://pubmed.ncbi.nlm.nih.gov/30597128/
In vivo activity:
In order to assess the effect of CyPPA on spontaneous exploratory locomotor activity, the compound was administered to otherwise un-treated NMRI mice exposed to a novel environment (see Materials and Methods for details). As shown in Figure 6A, CyPPA significantly reduced the total activity level over the 30 min test session at a dose of 30 mg/kg [F(3,167) = 31.5, P < 0.001], but was devoid of effect at doses of 3 and 10 mg/kg.
Reference: Front Pharmacol. 2012; 3: 11. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3278045/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
28.5 |
100.00 |
| Ethanol |
28.5 |
100.00 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
285.40
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Noh TK, Bang SH, Lee YJ, Cho HI, Jung MY, Kim I, Leem CH, Chang SE. The ion channel activator CyPPA inhibits melanogenesis via the GSK3β/β-catenin pathway. Chem Biol Interact. 2019 Feb 25;300:1-7. doi: 10.1016/j.cbi.2018.12.014. Epub 2018 Dec 28. PMID: 30597128.
2. Herrik KF, Redrobe JP, Holst D, Hougaard C, Sandager-Nielsen K, Nielsen AN, Ji H, Holst NM, Rasmussen HB, Nielsen EØ, Strøbæk D, Shepard PD, Christophersen P. CyPPA, a Positive SK3/SK2 Modulator, Reduces Activity of Dopaminergic Neurons, Inhibits Dopamine Release, and Counteracts Hyperdopaminergic Behaviors Induced by Methylphenidate. Front Pharmacol. 2012 Feb 13;3:11. doi: 10.3389/fphar.2012.00011. PMID: 22347859; PMCID: PMC3278045.
3. Skarra DV, Cornwell T, Solodushko V, Brown A, Taylor MS. CyPPA, a positive modulator of small-conductance Ca(2+)-activated K(+) channels, inhibits phasic uterine contractions and delays preterm birth in mice. Am J Physiol Cell Physiol. 2011 Nov;301(5):C1027-35. doi: 10.1152/ajpcell.00082.2011. Epub 2011 Jul 27. PMID: 21795518.
In vitro protocol:
1. Noh TK, Bang SH, Lee YJ, Cho HI, Jung MY, Kim I, Leem CH, Chang SE. The ion channel activator CyPPA inhibits melanogenesis via the GSK3β/β-catenin pathway. Chem Biol Interact. 2019 Feb 25;300:1-7. doi: 10.1016/j.cbi.2018.12.014. Epub 2018 Dec 28. PMID: 30597128.
In vivo protocol:
1. Herrik KF, Redrobe JP, Holst D, Hougaard C, Sandager-Nielsen K, Nielsen AN, Ji H, Holst NM, Rasmussen HB, Nielsen EØ, Strøbæk D, Shepard PD, Christophersen P. CyPPA, a Positive SK3/SK2 Modulator, Reduces Activity of Dopaminergic Neurons, Inhibits Dopamine Release, and Counteracts Hyperdopaminergic Behaviors Induced by Methylphenidate. Front Pharmacol. 2012 Feb 13;3:11. doi: 10.3389/fphar.2012.00011. PMID: 22347859; PMCID: PMC3278045.
2. Skarra DV, Cornwell T, Solodushko V, Brown A, Taylor MS. CyPPA, a positive modulator of small-conductance Ca(2+)-activated K(+) channels, inhibits phasic uterine contractions and delays preterm birth in mice. Am J Physiol Cell Physiol. 2011 Nov;301(5):C1027-35. doi: 10.1152/ajpcell.00082.2011. Epub 2011 Jul 27. PMID: 21795518.
1: Herrik KF, Redrobe JP, Holst D, Hougaard C, Sandager-Nielsen K, Nielsen AN, Ji H, Holst NM, Rasmussen HB, Nielsen EØ, Strøbæk D, Shepard PD, Christophersen P. CyPPA, a Positive SK3/SK2 Modulator, Reduces Activity of Dopaminergic Neurons, Inhibits Dopamine Release, and Counteracts Hyperdopaminergic Behaviors Induced by Methylphenidate. Front Pharmacol. 2012 Feb 13;3:11. doi: 10.3389/fphar.2012.00011. eCollection 2012. PubMed PMID: 22347859; PubMed Central PMCID: PMC3278045.
2: Dolga AM, Letsche T, Gold M, Doti N, Bacher M, Chiamvimonvat N, Dodel R, Culmsee C. Activation of KCNN3/SK3/K(Ca)2.3 channels attenuates enhanced calcium influx and inflammatory cytokine production in activated microglia. Glia. 2012 Dec;60(12):2050-64. doi: 10.1002/glia.22419. Epub 2012 Sep 21. PubMed PMID: 23002008; PubMed Central PMCID: PMC3799773.
