Meprylcaine

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

Meprylcaine
Legal status
Legal status
Identifiers
IUPAC name
  • benzoic acid (2-methyl-2-propylaminopropyl) ester
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H21NO2
Molar mass235.327 g·mol−1
3D model (JSmol)
SMILES
  • CC(COC(C1=CC=CC=C1)=O)(C)NCCC
InChI
  • 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 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. Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T (February 2000). "Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics". Naunyn-Schmiedeberg's Archives of Pharmacology. 361 (2): 214–20. doi:10.1007/s002109900184. PMID 10685879. S2CID 1627097.
  2. Arai S, Morita K, Kitayama S, Kumagai K, Kumagai M, Kihira K, Dohi T (February 2003). "Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics". Brain Research. 964 (1): 83–90. doi:10.1016/S0006-8993(02)04068-4. PMID 12573515. S2CID 16539422.
  3. Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, et al. (September 2005). "Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities" (PDF). Brain Research. 1057 (1–2): 153–60. doi:10.1016/j.brainres.2005.07.049. PMID 16125150. S2CID 30437231.
  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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