U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C16H23NO2.ClH
Molecular Weight 297.82
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPEROCAINE HYDROCHLORIDE

SMILES

Cl.CC1CCCCN1CCCOC(=O)C2=CC=CC=C2

InChI

InChIKey=ZXSGQNYQJIUMQN-UHFFFAOYSA-N
InChI=1S/C16H23NO2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H23NO2
Molecular Weight 261.3593
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Piperocaine (Metycaine) is a local anesthetic drug. It is an ester and primarily is a sodium channel blocker. Piperocaine can partially inhibit dopamine. It is known as a alpha-1-proteinase inhibitor. Used in the form of its hydrochloride as a local or spinal anesthetic and in dental anesthesia. Can cause toxic reactions. Piperocaine Hydrochloride is in the list of Bulk Drug Substances Nominated for Use in Compounding Under Section 503A, FDA Act. Piperocaine hydrochloride is a small, white odorless crystals or a white crystalline powder, stable in air, freely soluble in water, alcohol and chloroform.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Metycaine Hydrochloride

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
For continuous caudal analgesia in obstetrics initial dose of 30 ml of 1 and 1.5 % metycaine produced analgesia as high as the line midway between the pubis and the umbilicus and relieved the pains of labor.
Route of Administration: Other
In Vitro Use Guide
At a maximum concentration of 100 uM, the ester containing local anesthetics procaine, tetracaine, piperocaine and the amide containing local anesthetic dibucaine and bupivacaine partially inhibited dopamine uptake by 47-70%
Substance Class Chemical
Record UNII
Q2RH0XR1MB
Record Status Validated (UNII)
Record Version