IcilinAG-3-5

Modify Date: 2025-08-21 10:54:51

IcilinAG-3-5 Structure
IcilinAG-3-5 structure
Common Name IcilinAG-3-5
CAS Number 36945-98-9 Molecular Weight 311.292
Density 1.4±0.1 g/cm3 Boiling Point 594.8±50.0 °C at 760 mmHg
Molecular Formula C16H13N3O4 Melting Point 200-208ºC
MSDS Chinese USA Flash Point 313.5±30.1 °C

 Use of IcilinAG-3-5


Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.IC50 value:Target: TRPM8in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].in vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, s.c.). Shaking behavior caused by a fixed dose (2.5mg/kg) of icilin was also inhibited in a dose-related manner by clonidine pretreatment (0.03-0.15 mg/kg, s.c.) and reduced by clonidine posttreatment (0.15 mg/kg, s.c.) [3].

 Names

Name 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one
Synonym More Synonyms

 IcilinAG-3-5 Biological Activity

Description Icilin(AG 3-5) is a synthetic super-agonist of TRPM8 ion channel.IC50 value:Target: TRPM8in vitro: icilin, a super-cooling agent, down-regulated the expression of cell cycle signature genes and caused G1 arrest in PC-3 prostate cancer cells. icilin affected cell cycle-related transcriptional modules and identified E2F1 transcription factor as a target master regulator of icilin. icilin reduced the activity and expression levels of E2F1 [1]. Icilin concentration-response curves were significantly shifted to the right when pH was lowered from 7.3 to 6.9, whereas those with menthol were unaltered in solutions of pH 6.1 [2]. Icilin modulated the expression level of various cell cycle regulators at transcription or post-translational levels. In addition, icilin activated JNK and p38 kinase pathways, but not ERK [4].in vivo: Rats injected with icilin (0.5, 1, 2.5, 5mg/kg, i.p.) displayed dose-related WDS that were inhibited by pretreatment with a fixed dose of clonidine (0.15 mg/kg, s.c.). Shaking behavior caused by a fixed dose (2.5mg/kg) of icilin was also inhibited in a dose-related manner by clonidine pretreatment (0.03-0.15 mg/kg, s.c.) and reduced by clonidine posttreatment (0.15 mg/kg, s.c.) [3].
Related Catalog
References

[1]. Lee S, et al. Icilin inhibits E2F1-mediated cell cycle regulatory programs in prostate cancer. Biochem Biophys Res Commun. 2013 Nov 29;441(4):1005-10.

[2]. Andersson DA, et al. TRPM8 activation by menthol, icilin, and cold is differentially modulated by intracellular pH. J Neurosci. 2004 Jun 9;24(23):5364-9.

[3]. Kim J, et al. Icilin-evoked behavioral stimulation is attenuated by alpha-adrenoceptor activation. Brain Res. 2011 Apr 12;1384:110-7.

[4]. Kim SH, et al. Icilin induces G1 arrest through activating JNK and p38 kinase in a TRPM8-independent manner. Biochem Biophys Res Commun. 2011 Mar 4;406(1):30-5.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 594.8±50.0 °C at 760 mmHg
Melting Point 200-208ºC
Molecular Formula C16H13N3O4
Molecular Weight 311.292
Flash Point 313.5±30.1 °C
Exact Mass 311.090607
PSA 98.39000
LogP 2.73
Vapour Pressure 0.0±1.7 mmHg at 25°C
Index of Refraction 1.672
Storage condition -20℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UW7397500
CHEMICAL NAME :
2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-
CAS REGISTRY NUMBER :
36945-98-9
BEILSTEIN REFERENCE NO. :
0700310
LAST UPDATED :
199612
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C16-H13-N3-O4
MOLECULAR WEIGHT :
311.32

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation in microorganisms
TEST SYSTEM :
Bacteria - Salmonella typhimurium
DOSE/DURATION :
700 ug/plate
REFERENCE :
JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 35,110,1983

 Safety Information

Hazard Codes Xn: Harmful;
Risk Phrases R20/21/22
Safety Phrases 26-36
HS Code 2933599090

 Customs

HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

MFCD01689072
Icilin
3-(2-Hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydro-2(1H)-pyrimidinone
2(1H)-Pyrimidinone, 3,6-dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-
AG-3-5
3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-3,4-dihydropyrimidin-2(1H)-one
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