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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
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
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

1933
6
Targets

Targets

Primary TargetPharmacologyConditionPotency
Blocker
537
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
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:
https://pubmed.ncbi.nlm.nih.gov/15402120/
unhealthy, 10-90
n = 57
Health Status: unhealthy
Condition: dental surgery
Age Group: 10-90
Sex: M+F
Population Size: 57
Sources:
https://pubmed.ncbi.nlm.nih.gov/15402120/
Sourcing

Sourcing

Vendor/AggregatorIDURL
ABI Chem
AC1L1VXK
Alfa Chemistry
ACM533288
BOC Sciences
136-82-3
ChemMol
99070272
http://www.chemmol.com/chemmol/99070272.html
Chemieliva Pharmaceutical Co., Ltd
PBCM1168098
Compound Cloud
10781
Compound Cloud
10782
MuseChem
M071487
MuseChem
R070736
NovoSeek
10782
Parchem
58000
https://www.parchem.com/chemical-supplier-distributor/Piperocaine-058000.aspx
Sigma Aldrich
S403253
Sigma Aldrich
S403253|ALDRICH
THE BioTek
bt-372036
https://www.thebiotek.com/product/others/bt-372036
TimTec
ST50443593
ZINC
ZINC000002034887
http://zinc15.docking.org/substances/ZINC000002034887
ZINC
ZINC000002034888
http://zinc15.docking.org/substances/ZINC000002034888
eMolecules
10170459
eMolecules
110057371
eMolecules
300113982
mcule
MCULE-4599192331
https://mcule.com/MCULE-4599192331/
PubMed

PubMed

TitleDatePubMed
Patents

Patents

US2016030408
7
US2016030476
5
US2016038462
3
US2016045413
5
US2016051516
2
US2016058752
2
US2016074515
2
US2016082038
2
US2016082150
5

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
Created
by admin
on Sat Dec 16 01:02:04 UTC 2023
Edited
by admin
on Sat Dec 16 01:02:04 UTC 2023
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 [WHO-DD]
Common 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
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 Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL127865
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
SMS_ID
100000138600
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
MERCK INDEX
m8857
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID2046709
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
PUBCHEM
10781
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
FDA UNII
Q2RH0XR1MB
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
NCI_THESAURUS
C90655
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
CAS
533-28-8
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
EVMPD
SUB78164
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
MESH
C023039
Created by admin on Sat Dec 16 01:02:04 UTC 2023 , Edited by admin on Sat Dec 16 01:02:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of PIPEROCAINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PIPEROCAINE
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