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	UK: Under Psychoactive Substances Act
Identifiers
IUPAC name benzoic acid (2-methyl-2-propylaminopropyl) ester
CAS Number	495-70-5
PubChem CID	4065
ChemSpider	3925
UNII	82YT7WU9PW
ChEMBL	ChEMBL127810
CompTox Dashboard (EPA)	DTXSID70197810
Chemical and physical data
Formula	C14H21NO2
Molar mass	235.327 g·mol^−1
3D model (JSmol)	Interactive image
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]

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.
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.
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.