Amylocaine

Amylocaine

Names
IUPAC name [1-(Dimethylamino)-2-methylbutan-2-yl] benzoate
Other names Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
CAS Number	644-26-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1740065 Error creating thumbnail: N
ChemSpider	10312 Y
ECHA InfoCard
EC Number	211-411-1
E number
KEGG	D07454 Y
PubChem CID	10767
UNII	QRW683O56T Y
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI InChI=1S/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3 Y Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N Y InChI=1/C14H21NO2/c1-5-14(2,11-15(3)4)17-13(16)12-9-7-6-8-10-12/h6-10H,5,11H2,1-4H3 Key: FDMBBCOBEAVDAO-UHFFFAOYAQ
SMILES O=C(OC(C)(CC)CN(C)C)c1ccccc1
Properties
Chemical formula	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). Error creating thumbnail: N verify (what is YError creating thumbnail: N ?) Infobox references

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).

File:Amylocaine synthesis.svg

Synthesis of amylocaine

See also

• Dimethylaminopivalophenone, an opioid with a similar chemical structure