Amylocaine

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

Chemical compound

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

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).^[3]^[4]

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.
^ ^a ^b Quintard, Jean-Paul; Elissondo, Bernard; Jousseaume, Bernard (1984). "A Convenient Synthesis of N,N-Disubstituted Aminomethyltri-n-butylstannanes, Precursors of the Corresponding Lithium Reagents". Synthesis. 1984 (6): 495–498. doi:10.1055/s-1984-30879. ISSN 0039-7881. S2CID 95920500.
^ ^a ^b Fourneau, Ernest (1904). Comptes rendus hebdomadaires des séances de l'Académie des sciences. Vol. 138. Paris: Academy of Sciences, Centre national de la recherche scientifique (CNRS; French National Centre for Scientific Research). p. 767.
^ Zernik, F (1905). "?". Chem. Zentralbl. 76 (1): 1029.^{[full citation needed]}
^ DE169746C, "Patent number DE169746C" . Google Patents.
^ DE169787C, "Patent number DE169787C" . Google Patents.

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. doi:10.1177/0310057X0403200201. PMID 15957711.

Local anesthetics (primarily sodium channel blockers) (N01B)

Esters by acid

Aminobenzoic	Benzocaine Benzonatate Butacaine Butamben Chloroprocaine Dimethocaine Lucaine Meprylcaine Metabutethamine Metabutoxycaine Nitracaine Orthocaine Propoxycaine Procaine (Novocaine) Proxymetacaine Risocaine Tetracaine
Benzoic	Amylocaine Cocaine Cyclomethycaine α-Eucaine β-Eucaine Hexylcaine Isobucaine Piperocaine
ArCO2- (not para-amino or Ph)	Amoproxan (3,4,5-Trimethoxybenzoyl) 3-(p-Fluorobenzoyloxy)tropane