meprylcaine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = benzoic acid (2-methyl-2-propylaminopropyl) ester

| image = Epirocaine.svg

| width = 220

| tradename =

| routes_of_administration =

| legal_status =

| legal_UK = PSA

| CAS_number = 495-70-5

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 82YT7WU9PW

| ATC_suffix =

| PubChem = 4065

| ChEMBL = 127810

| ChemSpiderID = 3925

| C=14 | H=21 | N=1 | O=2

| smiles = CC(COC(C1=CC=CC=C1)=O)(C)NCCC

| StdInChI = 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

| StdInChIKey = VXJABHHJLXLNMP-UHFFFAOYSA-N

}}

Meprylcaine (also known as Epirocaine and Oracaine) is a local anesthetic with stimulant properties that is structurally related to dimethocaine.{{cite journal | vauthors = Sato T, Kitayama S, Mitsuhata C, Ikeda T, Morita K, Dohi T | title = Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 361 | issue = 2 | pages = 214–20 | date = February 2000 | pmid = 10685879 | doi = 10.1007/s002109900184 | s2cid = 1627097 }}

Meprylcaine has a relatively potent inhibitory action on the monoamine transporter and inhibits the reuptake of dopamine, norepinephrine and serotonin.{{cite journal | vauthors = Arai S, Morita K, Kitayama S, Kumagai K, Kumagai M, Kihira K, Dohi T | title = Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics | journal = Brain Research | volume = 964 | issue = 1 | pages = 83–90 | date = February 2003 | pmid = 12573515 | doi = 10.1016/S0006-8993(02)04068-4 | s2cid = 16539422 | url = http://ir.lib.hiroshima-u.ac.jp/00000113 }}{{cite journal | vauthors = Morita K, Hamamoto M, Arai S, Kitayama S, Irifune M, Kawahara M, Kihira K, Dohi T | display-authors = 6 | title = Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities | journal = Brain Research | volume = 1057 | issue = 1–2 | pages = 153–60 | date = September 2005 | pmid = 16125150 | doi = 10.1016/j.brainres.2005.07.049 | s2cid = 30437231 | url = http://ir.lib.hiroshima-u.ac.jp/files/public/0/115/20141016115526561231/Brain-Res_1057-1-2_153-160_2005-9-28.pdf | access-date = 2019-12-11 | archive-date = 2017-08-17 | archive-url = 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 | url-status = dead }}