Meprylcaine

Meprylcaine

Systematic (IUPAC) name
benzoic acid (2-methyl-2-propylaminopropyl) ester
Identifiers
CAS Number	495-70-5
PubChem	CID 4065
ChemSpider	3925
ChEMBL	CHEMBL127810
Chemical data
Formula	C14H21NO2
Molar mass	235.33 g·mol^−1
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 (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]

References

1. T. Sato, S. Kitayama, C. Mitsuhata, T. Ikeda, K. Morita, T. Dohi (February 2000). "Selective inhibition of monoamine neurotransmitter transporters by synthetic local anesthetics". Naunyn-Schmiedeberg's Archives of Pharmacology 361 (2): 214–220. doi:10.1007/s002109900184. PMID 10685879.
2. Shigeaki Arai, Katsuya Morita, Shigeo Kitayama, Kei Kumagai, Michio Kumagai, Kenji Kihira, Toshihiro Dohi (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.
3. Katsuya Morita, Masahiro Hamamoto, Shigeaki Arai, Shigeo Kitayama, Masahiro Irifune, Michio Kawahara, Kenji Kihira, Toshihiro Dohi (September 2005). "Inhibition of serotonin transporters by cocaine and meprylcaine through 5-HT_2C receptor stimulation facilitates their seizure activities". Brain Research 1057 (1–2): 153–160. doi:10.1016/j.brainres.2005.07.049. PMID 16125150.