Chemistry:Meprylcaine

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Short description: Chemical compound
Meprylcaine
Epirocaine.svg
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC14H21NO2
Molar mass235.327 g·mol−1
3D model (JSmol)

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. "Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics". Naunyn-Schmiedeberg's Archives of Pharmacology 361 (2): 214–20. February 2000. doi:10.1007/s002109900184. PMID 10685879. 
  2. "Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics". Brain Research 964 (1): 83–90. February 2003. doi:10.1016/S0006-8993(02)04068-4. PMID 12573515. http://ir.lib.hiroshima-u.ac.jp/00000113. 
  3. "Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities". Brain Research 1057 (1–2): 153–60. September 2005. doi:10.1016/j.brainres.2005.07.049. PMID 16125150. http://ir.lib.hiroshima-u.ac.jp/files/public/0/115/20141016115526561231/Brain-Res_1057-1-2_153-160_2005-9-28.pdf. 
  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).