Amylocaine

Amylocaine
Names
	IUPAC name benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
CAS Number	644-26-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1740065 ;
ChemSpider	10312 ;
ECHA InfoCard	100.010.375
EC Number	211-411-1;
KEGG	D07454 ;
PubChem CID	10767;
UNII	QRW683O56T ;
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 Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N ; 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).

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]

Notes and references

^ Fourneau, E. (1904). "Stovaïne, anesthésique local". Bulletin des sciences pharmacologiques. 10: 141-148.
^ 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.

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.

Names

IUPAC name benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
CAS Number	644-26-8
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1740065
ChemSpider	10312
ECHA InfoCard	100.010.375
EC Number	211-411-1
KEGG	D07454
PubChem CID	10767
UNII	QRW683O56T
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 Key: FDMBBCOBEAVDAO-UHFFFAOYSA-N 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).