amylocaine

Also known as 1-(dimetylaminometyl)-1-metylpropyl benzoate

Amylocaine was the first synthetic local anesthetic. It was synthesized and patented under the name Stovaine by Ernest Fourneau at the Pasteur Institute in 1903. It was used mostly in spinal anesthesia.

In the Vinony graph

Within Vinony's link graph, amylocaine is referenced by 369 other articles, and connects out to local anesthetic, Wayback Machine and cocaine.

Vinony files it under Benzoate esters, Chembox image size set and Dimethylamino compounds.

Its subject is documented across 11 Wikipedia language editions.

Chemical data

Formula: C14H21NO2
Molecular weight: 235.32 g/mol
IUPAC name: [1-(dimethylamino)-2-methylbutan-2-yl] benzoate
SMILES: CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1
InChIKey: FDMBBCOBEAVDAO-UHFFFAOYSA-N
XLogP: 3
Polar surface area: 29.5 Å²
H-bond donors: 0
H-bond acceptors: 3
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 235.157229
Has use: medication

Show 2 more facts

chemical formula: C₁₄H₂₁NO₂
canonical SMILES: CCC(C)(CN(C)C)OC(=O)C1=CC=CC=C1

Sources (2)

via Wikidata · CC0

~1 min read

Encyclopedic overview

4 sections

Contents

Synthesis
See also
Notes and references
External links

==Synthesis== Amylocaine can be synthesized beginning with chloroacetone (1). Grignard reaction of chloroacetone with magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol (2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol (3). These two steps can also be treated as interchangeable. Esterification with benzoyl chloride completed the synthesis of amylocaine (4).

Excerpted from Wikipedia’s “amylocaine” article, available under the CC BY-SA 4.0 licence.