Ketocaine

Ketocaine

Clinical data
ATC code	None
Identifiers
IUPAC name 1-[2-[2-[di(propan-2-yl)amino]ethoxy]phenyl]butan-1-one
CAS Number	1092-46-2 14549-32-7 (HCl)
PubChem CID	68946
ChemSpider	62170
UNII	WA1RT89G9X
CompTox Dashboard (EPA)	DTXSID90862533
ECHA InfoCard	100.012.847
Chemical and physical data
Formula	C18H29NO2
Molar mass	291.435 g·mol−1
3D model (JSmol)	Interactive image
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

Ketocaine (INN; brand name Vericaina; former developmental codes Astra 2358 and 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]}

Synthesis

Williamson ether synthesis between 2'-hydroxybutyrophenone (1) and diisopropylaminoethyl chloride (2) gives ketocaine (3). ^{[4] [5] [6]}

Synthesis of ketocaine

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. Archived from the original on 10 January 2023. Retrieved 3 October 2016.
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. Re P, Verlicchi L, Setnikar I (March 1967). "β-Phenoxyethylamines with Local Anesthetic and Antispasmodic Activity". Journal of Medicinal Chemistry. 10 (2): 266–270. doi:10.1021/jm00314a036. PMID   6034076.
5. Re Paolo Da, Setnikar Ivo, U.S. patent 3,335,184 (1967 to S Chemiques Et Pharma Seceph S).
6. Prec