Hexylcaine
Basic information
- CAS
532-77-4- Standard SMILES
CC(CNC1CCCCC1)OC(=O)c1ccccc1- InChIKey
DKLKMKYDWHYZTD-UHFFFAOYSA-N- Molecular formula
- C16H23NO2
- Average molar mass
- 261.36 g/mol
- Monoisotopic mass
- 261.17287898
Overview
Hexylcaine is a benzoate ester.
Names & identifiers
- Preferred name
- Hexylcaine
- IUPAC
- 1-(cyclohexylamino)propan-2-yl benzoate
- English name
- Hexylcainc
- Molecular formula
- C16H23NO2
- Molecular weight
- 261.36
Names & synonyms
HEXYLCAINE1-(cyclohexylamino)propan-2-yl benzoateOsmocaine532-77-4HexilcainaHexylcainum1-(Cyclohexylamino)-2-propanol benzoate (ester)2-Propanol, 1-(cyclohexylamino)-, benzoate (ester)511IU0826ZDTXSID1047863RefChem:788314DTXCID7027839
Show more names
Hexylcainc1-(Cyclohexylamino)-2-propanol benzoate2-Propanol, 1-(cyclohexylamino)-, 2-benzoateBenzoic acid 2-cyclohexylamino-1-methylethyl esterBenzoic acid 1-(cyclohexylamino)-2-methylethyl ester
cyclaine /OD/ 1-(cyclohexylamino)-2-propanol benzoate esterHexylcaine [INN]Hexylcainum [INN-Latin]Hexilcaina [INN-Spanish](2-Cyclohexylamino-1-methylethyl) benzoateCyclain; OsmocaineCyclaine (TN)CHEBI:34791
Database identifiers
- CAS
532-77-4- PubChem CID
- 10770
- DTXSID
DTXSID1047863- ChEMBL
CHEMBL1197- ChEBI
CHEBI:34791- UNII
- 511IU0826Z
- EC Number
- 194-718-2
- Nikkaji
- J38.383J
Properties
Computed structural properties
- XLogP
- 3.6
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 6
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 268
Experimental & physicochemical properties
LogP3.9
Solubility9.71e-03 g/L
Melting Point177-178.5
Physical DescriptionSolid
Physicochemical properties
- Boiling point
- 385.3 · 385.3±25.0 °C(Predicted)
- Density
- 1.05 · 1.05±0.1 g/cm3(Predicted)
- solubility
- soluble in Dichloromethane
- form
- Solid
- pka
- 9.02 · 9.02±0.20(Predicted)
- color
- White
- FDA UNII
- 511 IU0826Z · 511IU0826Z
- Comptox DTXSID
- 1047863 · DTXSID1047863
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Toxicity
- LDLo par-man: 11 mL/kg:BAH,PUL JFSCAS5,501,1960
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
Pharmacodynamics
Hexylcaine is a local ester-class anesthetic. Local anesthetics produce a transient block of nerve conduction by interfering with sodium channels. This effect of the anesthetic interferes with the development of an action potential across the nerve.
Mechanism of Action
Hexyl caine acts mainly by inhibiting sodium influx through voltage gated sodium channels in the neuronal cell membrane of peripheral nerves. When the influx of sodium is interrupted, an action potential cannot arise and signal conduction is thus inhibited. The receptor site is thought to be located at the cytoplasmic (inner) portion of the sodium channel.
Biological Half-Life<10 minutes
Metabolism/MetabolitesHydrolyzed by plasma esterases to benzoic acid and other derivatives
Cellular LocationsExtracellular
Applications
UsesHexylcaine is an intermediate in the synthesis of Hexylcaine Hydrochloride which is used in pain management in as an antifungal agent. Anaesthetic.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Hexylcaine is a benzoate ester.
Related reactions
2 records
Compound notes
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