| Identification | Back Directory | [Name]
ICILIN | [CAS]
36945-98-9 | [Synonyms]
AG-3-5
ICILIN
Iciline
CS-1406
Icilin, >=98%
Icilin(AG 3-5)
AG 3-5; AG-3-5
Icilin,AG-3-5, >96%
3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1h)-pyrimidinon
1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-3,6-dihydropyrimidin-2(1H)-one
3-(2-HYDROXYPHENYL)-6-(3-NITROPHENYL)-3,4-DIHYDROPYRIMIDIN-2(1H)-ONE
3,6-DIHYDRO-1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-2(1H)-PYRIMIDINONE
2(1H)-Pyrimidinone,3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-
3,4-DIHYDRO-3-(2-HYDROXYPHENYL)-6-(3-NITROPHENYL)-(1H)-PYRIMIDIN-2-ONE
1-(2-HYDROXYPHENYL)-4-(3-NITROPHENYL)-1,2,3,6-TETRAHYDROPYRIMIDIN-2-ONE
3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,2,3,4-tetrahydropyrimidin-2-one
1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one
AG-3-5, 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one
ICILIN 1-(2-Hydroxyphenyl)-4-(3-nitrophenyl)-1,2,3,6-tetrahydropyrimidin-2-one | [Molecular Formula]
C16H13N3O4 | [MDL Number]
MFCD01689072 | [MOL File]
36945-98-9.mol | [Molecular Weight]
311.29 |
| Chemical Properties | Back Directory | [Boiling point ]
594.8±50.0 °C(Predicted) | [density ]
1.415±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO: 15 mg/mL, soluble
| [form ]
solid
| [pka]
9.94±0.35(Predicted) | [color ]
yellow
| [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 3 months. | [InChI]
InChI=1S/C16H13N3O4/c20-15-7-2-1-6-14(15)18-9-8-13(17-16(18)21)11-4-3-5-12(10-11)19(22)23/h1-8,10,20H,9H2,(H,17,21) | [InChIKey]
RCEFMOGVOYEGJN-UHFFFAOYSA-N | [SMILES]
C1(=O)N(C2=CC=CC=C2O)CC=C(C2=CC=CC([N+]([O-])=O)=C2)N1 |
| Hazard Information | Back Directory | [Description]
Icilin (36945-98-9) is an activator of cold-sensitive TRP channels with 2.5-fold greater efficacy and 200-fold greater potency than menthol (EC50?= 0.36 μM for CRM1, rat orthologue of TRPM8).1 Activator at TRPM8 (EC50?= 0.2 μM)2?and ANKTM1(TRPA1)3. Activator effects require Ca2+?and are pH dependent.2,4?Icilin induced G1?arrest in PC-3 prostate cancer cells without cell death.5 | [Uses]
Icilin has been used as cooling agent in anterior ventromedial preoptic area (VMPO) neurons. | [Definition]
ChEBI: 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one is a C-nitro compound. | [General Description]
Icilin is a synthetic cooling agent and modulates human transient receptor potential cation channel (TRPA1). Icilin inhibits transient receptor potential cation channel subfamily M member 8 (TRPM8) and modulates calcium release. Icilin also suppresses transient receptor potential vanilloid subtype 3 (TRPV3). | [Biological Activity]
Cooling agent that activates the novel cold receptors TRPM8 (CMR1) and TRPA1 (ANKTM1/TRPN1), members of the TRP ion channel family. Induces currents in CMR1-expressing HEK-293 cells (EC 50 = 0.36 μ M) more potently than menthol or low temperatures. Produces "wet shakes" in vivo . | [Biochem/physiol Actions]
Icilin is a potent agonist at the CMR1 cold- and menthol-sensitive receptor. | [storage]
Store at -20°C | [References]
1) McKemy?et al. (2002)?Identification of a cold receptor reveals a general role for TRP channels in thermosensation; Nature,?416?52
2) Andersson?et al. (2004)?TRPM8 activation by menthol, icilin and cold is differentially modulated by intracellular pH; J .Neurosci.,?24?5364
3) Story?et al. (2003)?ANKTM1, a TRP-like channel expressed in nociceptive neurons, is activated by cold temperatures; Cell,?112?819
4) Chuang?et al. (2004)?The super-cooling agent icilin reveals a mechanism of coincidence detection by a temperature-sensitive TRP channel; Neuron,?43?859
5) Kim?et al. (2011)?Icilin induces G1?arrest through activating JNK and p38 kinase in a TRPM8-independent manner; Biochem. Biophys. Res .Commun.,?406?30 |
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| Company Name: |
Sigma-Aldrich
|
| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
SPIRO PHARMA
|
| Telephone: |
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| Website: |
www.spiropharma.com.cn |
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