Structure via PubChem · Public domain (PubChem)
meprylcaine
Sign in to saveMeprylcaine (also known as Epirocaine and Oracaine) is a local anesthetic with stimulant properties that is structurally related to dimethocaine.
Chemical data
- Formula
- C14H21NO2
- Molecular weight
- 235.32 g/mol
- IUPAC name
- [2-methyl-2-(propylamino)propyl] benzoate
- SMILES
- CCCNC(C)(C)COC(=O)C1=CC=CC=C1
- InChIKey
- VXJABHHJLXLNMP-UHFFFAOYSA-N
- XLogP
- 2.9
- Polar surface area
- 38.3 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 235.157
Show 2 more facts
- canonical SMILES
- CCCNC(C)(C)COC(=O)C1=CC=CC=C1
- chemical formula
- C₁₄H₂₁NO₂
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
Meprylcaine (also known as Epirocaine and Oracaine) is a local anesthetic with stimulant properties that is structurally related to dimethocaine.
Meprylcaine has a relatively potent inhibitory action on the monoamine transporter and inhibits the reuptake of dopamine, norepinephrine and serotonin. ==Synthesis== [[File:Meprylcaine synthesis.svg|500px|center|thumb|Thieme Synthesis: Patents:]] 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).
Excerpted from Wikipedia’s “meprylcaine” article, available under the CC BY-SA 4.0 licence.
Available in 8 languages
via Wikidata sitelinks · CC0