Amylocaine

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

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]

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

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.
3. 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.
4. 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.
5. Zernik, F (1905). "?". Chem. Zentralbl. 76 (1): 1029.^{[ full citation needed ]}
6. DE169746C,"Patent number DE169746C" . Google Patents.
7. 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.