Piperocaine

Piperocaine is a local anesthetic drug developed in the 1920s and used as its hydrochloride salt for infiltration and nerve blocks.

Piperocaine
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • 3-(2-Methylpiperidin-1-yl)propyl benzoate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.784
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol−1
3D model (JSmol)
SMILES
  • CC1CCCCN1CCCOC(C2=CC=CC=C2)=O
InChI
  • InChI=1S/C16H23NO2/c1-14-8-5-6-11-17(14)12-7-13-19-16(18)15-9-3-2-4-10-15/h2-4,9-10,14H,5-8,11-13H2,1H3 N
  • Key:YQKAVWCGQQXBGW-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Synthesis
Synthesis:[1] Patent:[2]

Alkylation between 3-chloropropyl benzoate [942-95-0] (1) and Pipicoline [109-05-7] (2) provides piperocaine (3).

See also

References
  1. McElvain, S. M. (1927). "PIPERIDINE DERIVATIVES IV. SUBSTITUTED PIPERIDINE-ALKYL BENZOATES AND PARA-AMINOBENZOATES". Journal of the American Chemical Society 49 (11): 2835–2840. doi:10.1021/ja01410a030.
  2. Samuel M Mcelvain, U.S. Patent 1,784,903 (1930).

Further reading
  • Tiedt TN, Albuquerque EX, Bakry NM, Eldefrawi ME, Eldefrawi AT (November 1979). "Voltage- and time-dependent actions of piperocaine on the ion channel of the acetylcholine receptor". Molecular Pharmacology. 16 (3): 909–21. PMID 316855.[1]</ref>


  1. "A Preliminary Study of the Efficiency of Piperocaine Hydrochloride as a Local Anesthetic in Dental Surgery". The Journal of the American Dental Association. 40 (2): 163–169. 1950-02-01. doi:10.14219/jada.archive.1950.0022. ISSN 0002-8177.
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