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Piperocaine

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Chemical compound
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Pharmaceutical compound
Piperocaine
Clinical data
ATC code
  • none
Identifiers
  • 3-(2-Methylpiperidin-1-yl)propyl benzoate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.004.784Edit this at Wikidata
Chemical and physical data
FormulaC16H23NO2
Molar mass261.365 g·mol−1
3D model (JSmol)
  • CC1CCCCN1CCCOC(C2=CC=CC=C2)=O
  • 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
 ☒NcheckY (what is this?)  (verify)

Piperocaine is alocal anesthetic drug developed in the 1920s and used as itshydrochloridesalt forinfiltration andnerve blocks.

Synthesis

[edit]
Synthesis:[1] Patent:[2]

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

See also

[edit]

References

[edit]
  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

[edit]
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
Amides
Combinations
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
KCaTooltip Calcium-activated potassium channel
Blockers
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
ASICsTooltip Acid-sensing ion channel
Blockers
Chloride
CaCCsTooltip Calcium-activated chloride channel
Blockers
Activators
CFTRTooltip Cystic fibrosis transmembrane conductance regulator
Blockers
Activators
Unsorted
Blockers
Others
TRPsTooltip Transient receptor potential channels
LGICsTooltip Ligand gated ion channels


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  1. ^Costich, Emmett R. (1950-02-01)."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.doi:10.14219/jada.archive.1950.0022.ISSN 0002-8177.PMID 15402120.
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