Hexylcaine

Hexylcaine

Clinical data
ATC code	None
Pharmacokinetic data
Elimination half-life	<10 minutes
Identifiers
IUPAC name 1-cyclohexylaminopropan-2-yl benzoate
CAS Number	532-77-4^Y
PubChem CID	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 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.^[1]

Synthesis

Synthesis:^[2][3] Patent:^[4]

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).^{[citation needed]}

References

1. Spellberg MA (January 1959). "Hexylcaine (cyclaine) as topical anesthetic in gastroscopy and esophagoscopy". Gastroenterology. 36 (1): 120–1. doi:10.1016/S0016-5085(59)80102-5. PMID 13620024.
2. Cope, Arthur C.; Hancock, Evelyn M. (1944). "1-Alkylamino-2-propanols and their p-Nitro- and p-Aminobenzoates". Journal of the American Chemical Society 66 (9): 1453–1456. doi:10.1021/ja01237a010.
3. "Local Anesthetics". New England Journal of Medicine. 263 (19): 963–965.1960. doi:10.1056/NEJM196011102631912.
4. Cope Arthur C, U.S. patent 2,486,374 (1949 to Sharp & Dohme Inc).