Amylocaine

Names
IUPAC name benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
CAS Number	644-26-8 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1740065 N
ChemSpider	10312 Y
ECHA InfoCard	100.010.375
EC Number	211-411-1
KEGG	D07454 Y
PubChem CID	10767
UNII	QRW683O56T Y
CompTox Dashboard (EPA)	DTXSID6047862
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	235.32204
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) 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.^[1] It was used mostly in spinal anesthesia.^[2]

Synthesis

Synthesis:^[3][4][5] Patents:^[6][7]

Grignard reaction of chloroacetone (1) with one mole of magnesium ethyl bromide gives 1-chloro-2-methyl-butan-2-ol [74283-48-0] (2). Heating with dimethylamine gives 1-(dimethylamino)-2-methylbutan-2-ol [74347-10-7] (3). These two steps can also be treated as interchangeable. Esterification with benzoyl chloride completed the synthesis of amylocaine (4).