Structure via PubChem · Public domain (PubChem)
icilin
Sign in to saveIcilin (AG-3-5) is a synthetic super-agonist of the transient receptor potential M8 (TRPM8) ion channel. Although structurally not related to menthol, it produces an extreme sensation of cold, both in humans and animals. It is almost 200 times more potent than menthol, and 2.5 times more efficacious. Despite their similar effects, icilin activates the TRPM8 receptor in a different way than menthol does. Icilin has been shown to be effective in the treatment of pruritus in an experimental model of itch. It is now used as a research tool for the study of TRP channels, although despite its high p
Chemical data
- Formula
- C16H13N3O4
- Molecular weight
- 311.29 g/mol
- IUPAC name
- 3-(2-hydroxyphenyl)-6-(3-nitrophenyl)-1,4-dihydropyrimidin-2-one
- SMILES
- C1C=C(NC(=O)N1C2=CC=CC=C2O)C3=CC(=CC=C3)[N+](=O)[O-]
- InChIKey
- RCEFMOGVOYEGJN-UHFFFAOYSA-N
- XLogP
- 2.2
- Polar surface area
- 98.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 311.090606
Show 2 more facts
- chemical formula
- C₁₆H₁₃N₃O₄
- canonical SMILES
- C1C=C(NC(=O)N1C2=CC=CC=C2O)C3=CC(=CC=C3)[N+](=O)[O-]
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
Icilin (AG-3-5) is a synthetic super-agonist of the transient receptor potential M8 (TRPM8) ion channel. Although structurally not related to menthol, it produces an extreme sensation of cold, both in humans and animals. It is almost 200 times more potent than menthol, and 2.5 times more efficacious. Despite their similar effects, icilin activates the TRPM8 receptor in a different way than menthol does. Icilin has been shown to be effective in the treatment of pruritus in an experimental model of itch. It is now used as a research tool for the study of TRP channels, although despite its high potency it is less selective for TRPM8 over other related ion channels than are other compounds such as WS-12.
== References ==
Excerpted from Wikipedia’s “icilin” article, available under the CC BY-SA 4.0 licence.