Hexylcaine

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Template:Short description Template:Drugbox 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

File:Hexylcaine synthesis.svg
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).Script error: No such module "Unsubst".

References

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  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 2486374 (1949 to Sharp & Dohme Inc).

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