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Details

Stereochemistry RACEMIC
Molecular Formula C16H23NO2.ClH
Molecular Weight 297.8208
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPEROCAINE HYDROCHLORIDE

SMILES

CC1CCCCN1CCCOC(=O)c2ccccc2.Cl

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 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H23NO2
Molecular Weight 261.3599
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: Description was created using several sources including: http://www.annualreviews.org/doi/abs/10.1146/annurev.pa.09.040169.002443?journalCode=pharmtox.1; http://www.ncbi.nlm.nih.gov/pubmed/15402120; http://www.ncbi.nlm.nih.gov/pubmed/18149171; http://www.ncbi.nlm.nih.gov/pubmed/7635175; http://purl.bioontology.org/ontology/NDDF/003425; http://www.accessdata.fda.gov/scripts/animaldrugsatfda/details.cfm?dn=040-123 http://www.fda.gov/downloads/drugs/guidancecomplianceregulatoryinformation/pharmacycompounding/ucm467373.pdf; https://books.google.com/books?id=79BGAQAAMAAJ&pg=PA263&lpg=PA263&dq=METYCAINE+was+manufactured&source=bl&ots=-PQVR0IZgE&sig=9DfpIP-V1qufWzn5gmpEzdVfYVY&hl=en&sa=X&ved=0ahUKEwjr-qjk2rHLAhUJ8CYKHTG0DdkQ6AEILzAE#v=onepage&q=METYCAINE%20was%20manufactured&f=false

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Metycaine Hydrochloride

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Other AEs: Tremor, Tremor...
Other AEs:
Tremor (slight, 28.1%)
Tremor (moderate, 3.5%)
Sweating (slight, 17.5%)
Sweating (moderate, 1.8%)
Nervousness (slight, 29.8%)
Nervousness (moderate, 5.3%)
Nervousness (extreme, 8.8%)
Faintness (5.3%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Faintness 5.3%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Nervousness extreme, 8.8%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Sweating moderate, 1.8%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Tremor moderate, 3.5%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Nervousness moderate, 5.3%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Sweating slight, 17.5%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Tremor slight, 28.1%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
Nervousness slight, 29.8%
60 mg single, dental
Recommended
Dose: 60 mg
Route: dental
Route: single
Dose: 60 mg
Co-administed with::
epinephrine(1:60,000; single)
Sources:
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:

Sample Use Guides

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
Created
by admin
on Fri Jun 25 22:23:48 UTC 2021
Edited
by admin
on Fri Jun 25 22:23:48 UTC 2021
Record UNII
Q2RH0XR1MB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPEROCAINE HYDROCHLORIDE
GREEN BOOK   MI   WHO-DD  
Common Name English
3-(2-METHYLPIPERIDINO)PROPYL BENZOATE HYDROCHLORIDE
Systematic Name English
METYCAINE HYDROCHLORIDE
Brand Name English
PIPEROCAINE HYDROCHLORIDE [GREEN BOOK]
Common Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, BENZOATE (ESTER), HYDROCHLORIDE, (+/-)-
Common Name English
PIPEROCAINE HYDROCHLORIDE [MI]
Common Name English
PIPEROCAINE HCL
Common Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, 1-BENZOATE, HYDROCHLORIDE (1:1)
Common Name English
PIPEROCAINE HYDROCHLORIDE [WHO-DD]
Common Name English
3-BENZOXY-1-(2-METHYLPIPERIDINO)PROPANE HYDROCHLORIDE
Systematic Name English
NEOTHESIN HYDROCHLORIDE
Common Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, BENZOATE (ESTER), HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL127865
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
MERCK INDEX
M8857
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY Merck Index
EPA CompTox
533-28-8
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
PUBCHEM
10781
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
FDA UNII
Q2RH0XR1MB
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
NCI_THESAURUS
C90655
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
CAS
533-28-8
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
EVMPD
SUB78164
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
MESH
C023039
Created by admin on Fri Jun 25 22:23:48 UTC 2021 , Edited by admin on Fri Jun 25 22:23:48 UTC 2021
PRIMARY
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