Amylocaine
<templatestyles src="Chembox/styles.css"/>
Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox HazardsTemplate:Chembox Datapage checkTemplate:Yesno| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | Template:Chembox Elements/molecular formula |
| Molar mass | Template:Chem molar mass |
Template:Chembox Footer/tracking container onlyScript error: No such module "TemplatePar".Template:Short description
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]Script error: No such module "Unsubst". It was used mostly in spinal anesthesia.[2]
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
Notes and references
<templatestyles src="Reflist/styles.css" />
- ↑ Script error: No such module "Citation/CS1".
- ↑ Debue-Barazer, Christine (2007). "Les Implications scientifiques et industrielles du succès de la Stovaïne : Ernest Fourneau (1872–1949) et la chimie des médicaments en France" Template:Webarchive. Gesnerus 64 (1-2): 24-53.
- ↑ a b Script error: No such module "Citation/CS1".
- ↑ a b Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".Template:Full
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, "Patent number DE169746C"Script error: No such module "Check for unknown parameters".. Google Patents.
- ↑ <templatestyles src="Citation/styles.css"/>Template:Citation/make link, "Patent number DE169787C"Script error: No such module "Check for unknown parameters".. Google Patents.
Script error: No such module "Check for unknown parameters".
External links
- Script error: No such module "Citation/CS1".
- Script error: No such module "Citation/CS1".
Script error: No such module "Navbox".