10202. Icilin
Nomenclature
CAS number: 36945-98-9
3,6-Dihydro-1-(2-hydroxyphenyl)-4-(3-nitrophenyl)-2(1H)-pyrimidinone; 1-(2′-hydroxyphenyl)-4-(3″-nitrophenyl)-1,2,3,6-tetrahydropyrimidine-2-one; AG-3-5. C16H13N3O4; mol wt 311.29.
C 61.73%, H 4.21%, N 13.50%, O 20.56%.
Description and references
Peripheral cold channel agonist. Induces cold sensations when applied topically in humans, and intense shivering behavior in animal studies. Significantly more potent than menthol, q.v. Prepn: C. Podesva, J. M. Do Nascimento, DE 2142385; eidem, US 3821221 (1972, 1974 both to Delmar Chemicals). Description of cold producing properties: E. T. Wei, D. A. Seid, J. Pharm. Pharmacol. 35, 110 (1983) PubMed. Mechanism of action studies: H. Chuang et al., Neuron 43, 859 (2004) DOI PubMed; J. L. Werkheiser et al., Eur. J. Pharmacol. 547, 101 (2006) DOI PubMed.
