Structure via PubChem · Public domain (PubChem)
phenacaine
Sign in to savePhenacaine, also known as holocaine, is a local anesthetic. It is approved for ophthalmic use.
Chemical data
- Formula
- C18H22N2O2
- Molecular weight
- 298.4 g/mol
- IUPAC name
- N,N'-bis(4-ethoxyphenyl)ethanimidamide
- SMILES
- CCOC1=CC=C(C=C1)NC(=NC2=CC=C(C=C2)OCC)C
- InChIKey
- QXDAEKSDNVPFJG-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 42.9 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 298.168
Show 3 more facts
- chemical formula
- C₁₈H₂₂N₂O₂
- isomeric SMILES
- CCOC1=CC=C(C=C1)N/C(=N/C2=CC=C(C=C2)OCC)/C
- canonical SMILES
- CCOC1=CC=C(C=C1)NC(=NC2=CC=C(C=C2)OCC)C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Phenacaine, also known as holocaine, is a local anesthetic. It is approved for ophthalmic use.
==Synthesis== The synthesis of phenacaine begins with the condensation of p-phenetidine (1) with triethyl orthoacetate (2) to afford the imino ether (a Pinner salt, 3). Reaction of that intermediate with a second equivalent of the aniline results (4) in a net displacement of ethanol, probably by an addition-elimination scheme, producing the amidine, phenacaine (5).
Excerpted from Wikipedia’s “phenacaine” article, available under the CC BY-SA 4.0 licence.