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Details

Stereochemistry ACHIRAL
Molecular Formula C14H21NO2.ClH
Molecular Weight 271.783
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPRYLCAINE HYDROCHLORIDE

SMILES

Cl.CCCNC(C)(C)COC(=O)C1=CC=CC=C1

InChI

InChIKey=LKHWKAGQNOMUFQ-UHFFFAOYSA-N
InChI=1S/C14H21NO2.ClH/c1-4-10-15-14(2,3)11-17-13(16)12-8-6-5-7-9-12;/h5-9,15H,4,10-11H2,1-3H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/13709180 and http://www.ncbi.nlm.nih.gov/pubmed/14375393

Meprylcaine (also known as Epirocaine and Oracaine) is a local anesthetic with stimulant properties that is structurally related to dimethocaine. Meprylcaine has a relatively potent inhibitory action on the monoamine transporter and inhibits the reuptake of dopamine, norepinephrine and serotonin. Oracaine is commonly used as the hydrochloride salt and is compatible with the known vasoconstrictors. It has a slightly more rapid onset than procaine with a slight increase in potency. The earliest symptoms of a toxic overdose are stimulation to the central nervous system, thus following the same symptoms as procaine. Not more than 400 mg. (20 ml. of a 2 per cent solution) should be used at any one time for the ambulatory patient. Oracaine, like metycaine, may be used for patients sensitive to the para-aminobenzoic acid derivatives. Oracaine hydrochloride is used at present mainly by the dental profession and in dermatologic surgery.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.6 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics.
2003 Feb 21
Inhibition of serotonin transporters by cocaine and meprylcaine through 5-TH2C receptor stimulation facilitates their seizure activities.
2005 Sep 28
Patents

Sample Use Guides

2% solution of Oracaine for injections
Route of Administration: Parenteral
In Vitro Use Guide
Unknown
Name Type Language
MEPRYLCAINE HYDROCHLORIDE
JAN   MART.   MI   USP-RS   WHO-DD  
Common Name English
1-PROPANOL-2-METHYL-2-(PROPYLAMINO)-, BENZOATE (ESTER), HYDROCHLORIDE
Common Name English
MEPRYLCAINE HCL
Common Name English
MEPRYLCAINE HYDROCHLORIDE [JAN]
Common Name English
MEPRYLCAINE HYDROCHLORIDE [MI]
Common Name English
Meprylcaine hydrochloride [WHO-DD]
Common Name English
NSC-760071
Code English
MEPRYLCAINE HYDROCHLORIDE [MART.]
Common Name English
2-Methyl-2-(propylamino)-1-propanol benzoate (ester) hydrochloride
Common Name English
.BETA.-(N-PROPYLAMINO)-.BETA.,.BETA.-DIMETHYLETHYL BENZOATE HYDROCHLORIDE
Systematic Name English
2-METHYL-2-PROPYLAMINOPROPYL BENZOATE HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID4045341
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
CAS
956-03-6
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
FDA UNII
VR843X5GXG
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
NSC
760071
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
NCI_THESAURUS
C72819
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
MERCK INDEX
m307
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY Merck Index
PUBCHEM
101925
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
EVMPD
SUB03160MIG
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL127810
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
SMS_ID
100000086422
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY
ECHA (EC/EINECS)
213-475-6
Created by admin on Fri Dec 15 16:25:14 UTC 2023 , Edited by admin on Fri Dec 15 16:25:14 UTC 2023
PRIMARY