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amylocaine
Sign in to saveAlso 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.
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 Ų
- 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 sectionsContents
- Synthesis
- See also
- Notes and references
- External links
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.
==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.
Gallery (2)
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