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Details

Stereochemistry RACEMIC
Molecular Formula C16H23NO2
Molecular Weight 261.3593
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPEROCAINE

SMILES

CC1CCCCN1CCCOC(=O)C2=CC=CC=C2

InChI

InChIKey=YQKAVWCGQQXBGW-UHFFFAOYSA-N
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

HIDE SMILES / InChI

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
Mexoryl SX: a broad absorption UVA filter protects human skin from the effects of repeated suberythemal doses of UVA.
1998 Jun 15
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%
Name Type Language
PIPEROCAINE
INN   MI   WHO-DD  
INN  
Official Name English
.GAMMA.-(2-METHYLPIPERIDYL)PROPYL BENZOATE
Systematic Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, 1-BENZOATE
Common Name English
NEOTHESIN
Brand Name English
PIPEROCAINE [MI]
Common Name English
(±)-2-METHYL-1-PIPERIDINEPROPANOL BENZOATE
Systematic Name English
Piperocaine [WHO-DD]
Common Name English
ISOCAINE BASE
Common Name English
piperocaine [INN]
Common Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, BENZOATE (ESTER), (±)-
Common Name English
3-(2-METHYL-1-PIPERIDYL)PROPYL BENZOATE
Systematic Name English
(±)-3-BENZOXY-1-(2-METHYLPIPERIDINO)PROPANE
Systematic Name English
(2-METHYLPIPERIDINO)PROPYL BENZOATE
Systematic Name English
2-METHYL-1-PIPERIDINEPROPANOL BENZOATE
Systematic Name English
1-PIPERIDINEPROPANOL, 2-METHYL-, BENZOATE (ESTER)
Common Name English
METYCAINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
Code System Code Type Description
RXCUI
33752
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
205-262-1
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID8048315
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
FDA UNII
F66XUI6GZL
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
NCI_THESAURUS
C90654
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
EVMPD
SUB09871MIG
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
INN
4176
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
PUBCHEM
10782
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
MERCK INDEX
m8857
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PIPEROCAINE
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL127865
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
SMS_ID
100000081966
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
MESH
C023039
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
CAS
136-82-3
Created by admin on Fri Dec 15 15:17:41 GMT 2023 , Edited by admin on Fri Dec 15 15:17:41 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of PIPEROCAINE
SALT/SOLVATE (PARENT)
Structure of PIPEROCAINE HYDROCHLORIDE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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