Piperocaine

Piperocaine

Clinical data
ATC code	none
Identifiers
IUPAC name 3-(2-Methylpiperidin-1-yl)propyl benzoate
CAS Number	136-82-3  Y
PubChem CID	10782
ChemSpider	10326  N
UNII	F66XUI6GZL
ChEMBL	ChEMBL127865  N
CompTox Dashboard (EPA)	DTXSID8048315
ECHA InfoCard	100.004.784
Chemical and physical data
Formula	C16H23NO2
Molar mass	261.365 g·mol−1
3D model (JSmol)	Interactive image
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)

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

Synthesis

Synthesis: Patent:

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. doi:10.1016/S0026-895X(25)13832-7. PMID   316855. ^[1] </ref>

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.