Hexylcaine

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]

Hexylcaine
Clinical data
ATC code
  • None
Pharmacokinetic data
Elimination half-life<10 minutes
Identifiers
IUPAC name
  • 1-cyclohexylaminopropan-2-yl benzoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol−1
3D model (JSmol)
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
  (verify)

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).

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).
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