Ketocaine

Ketocaine (INN) (brand name Vericaina, former developmental code name Astra 2358 or A-2358) is an amino ether local anesthetic of the butyrophenone family used topically for pain relief. It is marketed in Italy.[1][2][3]

Ketocaine
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 1-[2-[2-[di(propan-2-yl)amino]ethoxy]phenyl]butan-1-one
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard100.012.847
Chemical and physical data
FormulaC18H29NO2
Molar mass291.435 g·mol−1
3D model (JSmol)
SMILES
  • CCCC(=O)C1=CC=CC=C1OCCN(C(C)C)C(C)C
InChI
  • InChI=InChI=1S/C18H29NO2/c1-6-9-17(20)16-10-7-8-11-18(16)21-13-12-19(14(2)3)15(4)5/h7-8,10-11,14-15H,6,9,12-13H2,1-5H3
  • Key:UXAWFWFJXIANHZ-UHFFFAOYSA-N

Synthesis
Synthesis:[4] Patent:[5] Prec

Williamson ether synthesis between 2'-hydroxybutyrophenone [2887-61-8] (1) and diisopropylaminoethyl chloride hydrochloride [4261-68-1] (2) gives Ketocaine (3)..

References
  1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 720–. ISBN 978-1-4757-2085-3.
  2. Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 159–. ISBN 978-94-011-4439-1.
  3. Woolfson D, McCafferty D (1 March 1993). Percutaneous Local Anaesthesia. CRC Press. pp. 88–. ISBN 978-0-13-656372-3.
  4. Da Re, Paolo.; Verlicchi, Lucia.; Setnikar, Ivo. (1967). "β-Phenoxyethylamines with Local Anesthetic and Antispasmodic Activity". Journal of Medicinal Chemistry. 10 (2): 266–270. doi:10.1021/jm00314a036.
  5. Re Paolo Da, Setnikar Ivo, U.S. Patent 3,335,184 (1967 to S Chemiques Et Pharma Seceph S).


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