Amylocaine
Chemical compound
From Wikipedia, the free encyclopedia
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.[1][contradictory] It was used mostly in spinal anesthesia.[2]
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| Names | |
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| IUPAC name
[1-(Dimethylamino)-2-methylbutan-2-yl] benzoate | |
| Other names
Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.010.375 |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C14H21NO2 | |
| Molar mass | 235.327 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Amylocaine can be synthesized beginning with chloroacetone (1).[3][4][5][6][7] 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).[3][4]
See also
- Dimethylaminopivalophenone, an opioid with a similar chemical structure