Hexylcaine

Clinical data
ATC code	None
Pharmacokinetic data
Eliminationhalf-life	<10 minutes
Identifiers
IUPAC name 1-cyclohexylaminopropan-2-yl benzoate
CAS Number	532-77-4 Y
PubChemCID	10770
IUPHAR/BPS	7196
DrugBank	DB00473 Y
ChemSpider	10315 Y
UNII	511IU0826Z
KEGG	C14172 Y
ChEMBL	ChEMBL1197 Y
CompTox Dashboard(EPA)	DTXSID1047863
Chemical and physical data
Formula	C16H23NO2
Molar mass	261.365 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC(CNC1CCCCC1)C)c2ccccc2
InChI InChI=1S/C16H23NO2/c1-13(12-17-15-10-6-3-7-11-15)19-16(18)14-8-4-2-5-9-14/h2,4-5,8-9,13,15,17H,3,6-7,10-12H2,1H3 Y Key:DKLKMKYDWHYZTD-UHFFFAOYSA-N Y
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Hexylcaine hydrochloride, also calledcyclaine (Merck) orosmocaine, is a short-actinglocal anesthetic. It acts by inhibitingsodium channel conduction. Overdose can lead toheadache,tinnitus,numbness and tingling around the mouth and tongue,convulsions,inability to breathe, and decreased heart function.^[1]

Synthesis

Thereductive amination between1-Amino-2-propanol [78-96-6] (1) andcyclohexanone gives 1-Cyclohexylamino-2-propanol [103-00-4] (2). Treatment withbenzoyl chloride gives the ester, completing the synthesis of Hexylcaine (3).^{[citation needed]}

References

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