Chemistry:Amylocaine
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| IUPAC name
benzoic acid [1-(dimethylaminomethyl)-1-methylpropyl] ester
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| 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). | |
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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]
See also
- Dimethylaminopivalophenone, an opioid with a similar structure–activity relationship (SAR). It is an amine that is a sole methylene spacer shorter.
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" . Gesnerus 64 (1-2): 24-53.
- ↑ 3.0 3.1 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. http://www.thieme-connect.de/DOI/DOI?10.1055/s-1984-30879.
- ↑ 4.0 4.1 Fourneau, Ernest (1904). Comptes rendus hebdomadaires des séances de l'Académie des sciences. 138. Paris: Academy of Sciences, Centre national de la recherche scientifique (CNRS; French National Centre for Scientific Research). pp. 767. https://www.biodiversitylibrary.org/item/31540#page/775/mode/1up.
- ↑ Zernik, F (1905). "?". Chem. Zentralbl 76 (1): 1029.[full citation needed]
- ↑ "Patent number DE169746C" patent DE169746C. Google Patents.
- ↑ "Patent number DE169787C" patent 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. http://jpet.aspetjournals.org/cgi/content/abstract/9/4/231.
- Ball, Christine M.; Westhorpe, Rod N. (2004). "Local Anaesthesia after Cocaine". Anaesthesia and Intensive Care 32 (2): 157. doi:10.1177/0310057X0403200201. PMID 15957711.
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