U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H21NO2
Molecular Weight 235.322
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPRYLCAINE

SMILES

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

InChI

InChIKey=VXJABHHJLXLNMP-UHFFFAOYSA-N
InChI=1S/C14H21NO2/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

HIDE SMILES / InChI

Molecular Formula C14H21NO2
Molecular Weight 235.322
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:17 UTC 2023
Edited
by admin
on Fri Dec 15 15:32:17 UTC 2023
Record UNII
82YT7WU9PW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPRYLCAINE
INN   MI   WHO-DD  
INN  
Official Name English
Meprylcaine [WHO-DD]
Common Name English
.BETA.-(N-PROPYLAMINO)-.BETA.,.BETA.-DIMETHYLETHYL BENZOATE
Systematic Name English
2-METHYL-2-PROPYLAMINOPROPYL BENZOATE
Systematic Name English
2-METHYL-2-(PROPYLAMINO)-1-PROPANOL BENZOATE (ESTER)
Common Name English
meprylcaine [INN]
Common Name English
MEPRYLCAINE [MI]
Common Name English
1-PROPANOL-2-METHYL-2-(PROPYLAMINO)-, BENZOATE (ESTER)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
WIKIPEDIA Designer-drugs-Meprylcaine
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
Code System Code Type Description
FDA UNII
82YT7WU9PW
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
PUBCHEM
4065
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
CAS
495-70-5
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
INN
370
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL127810
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
MERCK INDEX
m307
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID70197810
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
NCI_THESAURUS
C83931
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
SMS_ID
100000081501
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
DRUG CENTRAL
3770
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
EVMPD
SUB08760MIG
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
WIKIPEDIA
MEPRYLCAINE
Created by admin on Fri Dec 15 15:32:17 UTC 2023 , Edited by admin on Fri Dec 15 15:32:17 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY