Meprylcaine

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Meprylcaine
Legal status
Legal status
Identifiers
  • benzoic acid (2-methyl-2-propylaminopropyl) ester
JSmol)
  • CC(COC(C1=CC=CC=C1)=O)(C)NCCC
  • InChI=1S/C14H21NO2/c1-4-10-15-14(2,3)11-17-13(16)12-8-6-5-7-9-12/h5-9,15H,4,10-11H2,1-3H3
  • Key:VXJABHHJLXLNMP-UHFFFAOYSA-N

Meprylcaine (also known as Epirocaine and Oracaine) is a local anesthetic with stimulant properties that is structurally related to dimethocaine.[1]

Meprylcaine has a relatively potent inhibitory action on the monoamine transporter and inhibits the reuptake of dopamine, norepinephrine and serotonin.[2][3]

Synthesis

Thieme Synthesis:[4] Patents:[5][6]

The 2-methyl-2-(propylamino)propan-1-ol [55968-10-0] (1) is treated with base and then with Benzoyl chloride (2), completing the synthesis of Meprycaine (3).

References

  1. S2CID 1627097
    .
  2. S2CID 16539422
    .
  3. S2CID 30437231. Archived from the original
    (PDF) on 2017-08-17. Retrieved 2019-12-11.
  4. ^ Reasenberg, Julian R.; Goldberg, Samuel D. (1945). "Esters of β-Alkylaminoethanols". Journal of the American Chemical Society 67 (6): 933–939. doi:10.1021/ja01222a017.
  5. ^ Julian R Reasenberg, U.S. patent 2,767,207 (1956 to Mizzy Inc).
  6. ^ Julian R Reasenberg, Samuel D Goldberg, U.S. patent 2,421,129 (1947 to Oradent Chemical Co Inc).
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