Piperocaine

Chemical compound
  • none
Identifiers
  • 3-(2-Methylpiperidin-1-yl)propyl benzoate
CAS Number
  • 136-82-3 checkY
PubChem CID
  • 10782
ChemSpider
  • 10326 ☒N
UNII
  • F66XUI6GZL
ChEMBL
  • ChEMBL127865 ☒N
CompTox Dashboard (EPA)
  • DTXSID8048315 Edit this at Wikidata
ECHA InfoCard100.004.784 Edit this at WikidataChemical and physical dataFormulaC16H23NO2Molar mass261.365 g·mol−13D model (JSmol)
  • Interactive image
  • 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
 ☒NcheckY (what is this?)  (verify)

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

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

  • Hexylcaine

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>
  • v
  • t
  • e
Local anesthetics (primarily sodium channel blockers) (N01B)
Esters by acid
Aminobenzoic
Benzoic
ArCO2- (not para-amino or Ph)
  • Amoproxan (3,4,5-Trimethoxybenzoyl)
  • 3-(p-Fluorobenzoyloxy)tropane
AmidesCombinations
  • v
  • t
  • e
Calcium
VDCCsTooltip Voltage-dependent calcium channels
Blockers
Activators
Potassium
VGKCsTooltip Voltage-gated potassium channels
Blockers
Activators
IRKsTooltip Inwardly rectifying potassium channel
Blockers
Activators
  • GIRKTooltip G protein-coupled inwardly rectifying potassium channel-specific: ML-297 (VU0456810)
KCaTooltip Calcium-activated potassium channel
Blockers
  • BKCa-specific: Ethanol (alcohol)
  • GAL-021
Activators
K2PsTooltip Tandem pore domain potassium channel
Blockers
Activators
Sodium
VGSCsTooltip Voltage-gated sodium channels
Blockers
Activators
ENaCTooltip Epithelial sodium channel
Blockers
Activators
  • Solnatide
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
  • See here instead.
LGICsTooltip Ligand gated ion channels
  • See here instead.
See also: Receptor/signaling modulators • Transient receptor potential channel modulators


Stub icon

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  • v
  • t
  • e
  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.