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Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2
Molecular Weight 165.1891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICAINE

SMILES

CCOC(=O)C1=CC(N)=CC=C1

InChI

InChIKey=ZMCBYSBVJIMENC-UHFFFAOYSA-N
InChI=1S/C9H11NO2/c1-2-12-9(11)7-4-3-5-8(10)6-7/h3-6H,2,10H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/pro/tricaine-s.html | https://www.ncbi.nlm.nih.gov/pubmed/25090007 | https://www.ncbi.nlm.nih.gov/pubmed/6278838

Tricaine (MS-222, Tricaine-S), a water-soluble local anesthetic, is used commonly for sedation, immobilization, and anesthesia of poikilothermic animals and has been accepted as a common anesthetic for use in the cold-blooded animals. It has long been recognized as a valuable tool for the proper handling of these animals during manual spawning (fish stripping), weighing, measuring, marking, surgical operations, transport, photography, and research. Tricaine was developed by Merck as a sulfonated analog of benzocaine with high solubility in water. The main advantage of Tricaine is the short duration of action and rapid metabolism. There are many reports describing the use of Tricaine for anesthetizing poikilothermic animals because it is a safe agent for immersion anesthesia even though the other anesthetics such as ether, ethanol, thiopental, halothane, isoflurane, barbiturates also could be used. Amphibians could be anesthetized easily by immersion methods with Tricaine because the amphibian skin is extremely permeable and water is absorbed through the skin rather than ingested. Tricaine has been administered as an injectable agent also.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
0.05 % 1 times / day multiple, topical
Recommended
Dose: 0.05 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 1 times / day
Sources:
healthy, 62 years
n = 1
Health Status: healthy
Age Group: 62 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Vision decreased, Photophobia...
AEs leading to
discontinuation/dose reduction:
Vision decreased
Photophobia
Photopsia
Sources:
AEs

AEs

AESignificanceDosePopulation
Photophobia Disc. AE
0.05 % 1 times / day multiple, topical
Recommended
Dose: 0.05 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 1 times / day
Sources:
healthy, 62 years
n = 1
Health Status: healthy
Age Group: 62 years
Sex: M
Population Size: 1
Sources:
Photopsia Disc. AE
0.05 % 1 times / day multiple, topical
Recommended
Dose: 0.05 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 1 times / day
Sources:
healthy, 62 years
n = 1
Health Status: healthy
Age Group: 62 years
Sex: M
Population Size: 1
Sources:
Vision decreased Disc. AE
0.05 % 1 times / day multiple, topical
Recommended
Dose: 0.05 %, 1 times / day
Route: topical
Route: multiple
Dose: 0.05 %, 1 times / day
Sources:
healthy, 62 years
n = 1
Health Status: healthy
Age Group: 62 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Patents

Patents

Sample Use Guides

Leopard frogs required 100–250 mg/kg of MS-222 intracoelomically, and bullfrogs were anesthetized with 250–400 mg/kg of MS-222 intracoelomically. Larvae can be anesthetized with 50 mg/l, and adult frogs and salamanders require 200–300 mg/l.
Route of Administration: Other
Fish larvae were subjected electrical stimulation at room temperature using a custom-built electric stimulation set-up. Chambers with electrodes were filled with 2% agarose gel, such that the silver electrodes are completely within the gel. A circular well of volume 0.5 mL was created by removing the agarose in the centre of the chamber between the two electrodes. Fish are placed carefully into the well with desired orientation. Care was taken not to expose the electrodes to the fish swimming in the well. The electrodes are connected to a stimulator (Grass S-88, Grass Instruments, U.S.A) that generated square wave pulse trains of indicated lengths. Polarity of electrodes was reversed between pulse trains to avoid electrolysis. A range of stimulation regimes was tested, with the aim of attaining a brief twitch response, and all experiments shown used a train of 200 20 V pulses, with 0.5 ms pulse duration (100 ms total train duration) once every 5 seconds. Fish were measured before tricaine exposure, after exposure to 0.61 mM tricaine for 30 min and after #30 minutes of tricaine washout into fish water.
Name Type Language
TRICAINE
WHO-DD  
Common Name English
TRICAINE FREE BASE
Common Name English
BENZOIC ACID, 3-AMINO-, ETHYL ESTER
Common Name English
M-AMINOBENZOIC ACID ETHYL ESTER
Systematic Name English
3-ETHOXYCARBONYLBENZENEAMINE
Systematic Name English
ETHYL 3-AMINOBENZOATE
Systematic Name English
3-CARBETHOXYANILINE
Systematic Name English
NSC-39593
Code English
Tricaine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
Code System Code Type Description
RXCUI
1370418
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY RxNorm
DAILYMED
02591PHL19
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
CAS
582-33-2
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-482-9
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
MESH
C003636
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
NSC
39593
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
SMS_ID
300000023720
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
DRUG BANK
DB11552
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
WIKIPEDIA
Tricaine
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
NCI_THESAURUS
C84658
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
FDA UNII
02591PHL19
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
PUBCHEM
11400
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID1044011
Created by admin on Fri Dec 15 15:39:47 GMT 2023 , Edited by admin on Fri Dec 15 15:39:47 GMT 2023
PRIMARY