From Wikipedia, the free encyclopedia
Amylocaine
Names
IUPAC name
[1-(Dimethylamino)-2-methylbutan-2-yl] benzoate
Other names
Stovaine; Benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.010.375
EC Number
KEGG
UNII
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
O=C(OC(C)(CC)CN(C)C)c1ccccc1
Properties
C 14 H 21 N O 2
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).
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
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
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