Meprylcaine Explained

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

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).

Notes and References

1. Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T . Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics . Naunyn-Schmiedeberg's Archives of Pharmacology . 361 . 2 . 214–20 . February 2000 . 10685879 . 10.1007/s002109900184 . 1627097 .
2. Arai S, Morita K, Kitayama S, Kumagai K, Kumagai M, Kihira K, Dohi T . 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 . 12573515 . 10.1016/S0006-8993(02)04068-4 . 16539422 .
3. Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, Kihira K, Dohi T . 6 . 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 . 16125150 . 10.1016/j.brainres.2005.07.049 . 30437231 . 2019-12-11 . 2017-08-17 . https://web.archive.org/web/20170817012749/http://ir.lib.hiroshima-u.ac.jp/files/public/0/115/20141016115526561231/Brain-Res_1057-1-2_153-160_2005-9-28.pdf . dead .