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Structure via PubChem · Public domain (PubChem)
hexylcaine
Sign in to saveAlso known as Cyclaine®, Cyclaine, Hexilcaina, Hexylcainum
Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function. ==Synthesis== thumb|center|500px|Synthesis: Patent: The reductive amination between 1-Amino-2-propanol [78-96-6] (1) and cyclohexanone gives 1-Cyclohexylamino-2-propanol [103-00-4] (2). Treatment with benzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).
Chemical data
- Formula
- C16H23NO2
- Molecular weight
- 261.36 g/mol
- IUPAC name
- 1-(cyclohexylamino)propan-2-yl benzoate
- SMILES
- CC(CNC1CCCCC1)OC(=O)C2=CC=CC=C2
- InChIKey
- DKLKMKYDWHYZTD-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1982
- Admin. routes
- topical
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 261.172879
- Has use
- medication
Show 2 more facts
- chemical formula
- C₁₆H₂₃NO₂
- canonical SMILES
- CC(CNC1CCCCC1)OC(=O)C2=CC=CC=C2
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Hexylcaine hydrochloride, also called cyclaine (Merck) or osmocaine, is a short-acting local anesthetic. It acts by inhibiting sodium channel conduction. Overdose can lead to headache, tinnitus, numbness and tingling around the mouth and tongue, convulsions, inability to breathe, and decreased heart function. ==Synthesis== thumb|center|500px|Synthesis: Patent: The reductive amination between 1-Amino-2-propanol [78-96-6] (1) and cyclohexanone gives 1-Cyclohexylamino-2-propanol [103-00-4] (2). Treatment with benzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).
==References==
Excerpted from Wikipedia’s “hexylcaine” article, available under the CC BY-SA 4.0 licence.