Hexylcaine

Source: Wikipedia, the free encyclopedia.
Hexylcaine
Clinical data
ATC code
  • None
Pharmacokinetic data
Elimination half-life<10 minutes
Identifiers
  • 1-cyclohexylaminopropan-2-yl benzoate
JSmol)
  • O=C(OC(CNC1CCCCC1)C)c2ccccc2
  • 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 checkY
  • Key:DKLKMKYDWHYZTD-UHFFFAOYSA-N checkY
  (verify)

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

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. 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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