![]() | |
Names | |
---|---|
IUPAC name
[1-(Dimethylamino)-2-methylbutan-2-yl] benzoate
| |
Other names
Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.375 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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] It was used mostly in spinal anesthesia. [2]
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]
![]() | |
Names | |
---|---|
IUPAC name
[1-(Dimethylamino)-2-methylbutan-2-yl] benzoate
| |
Other names
Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.010.375 |
EC Number |
|
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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).
|
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] It was used mostly in spinal anesthesia. [2]
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]