Amylocaine

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]

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 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	235.327 g·mol−1
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

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]

Synthesis of amylocaine

See also

• Dimethylaminopivalophenone, an opioid with a similar chemical structure