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] It used to be used mostly in spinal anesthesia.[2]

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

See also

• Dimethylaminopivalophenone, an opioid with a similar structure–activity relationship (SAR). It's an amine that is a sole methylene spacer shorter.

Notes and references

1. Fourneau, E. (1904). "Stovaïne, anesthésique local". Bulletin des sciences pharmacologiques. 10: 141-148.
2. 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" Archived 2013-10-05 at the Wayback Machine. Gesnerus 64 (1-2): 24-53.

External links

• Smith, Maurice I.; Hatcher, Robert A. (January 1917). "A Contribution to the Pharmacology of Stovaine". Journal of Pharmacology and Experimental Therapeutics. 9 (4): 231–240.
• Ball, Christine M.; Westhorpe, Rod N. (2004). "Local Anaesthesia after Cocaine". Anaesthesia and Intensive Care. 32 (2): 157. PMID 15957711.