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Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2.CH4O3S
Molecular Weight 261.295
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICAINE METHANESULFONATE

SMILES

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

InChI

InChIKey=FQZJYWMRQDKBQN-UHFFFAOYSA-N
InChI=1S/C9H11NO2.CH4O3S/c1-2-12-9(11)7-4-3-5-8(10)6-7;1-5(2,3)4/h3-6H,2,10H2,1H3;1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H11NO2
Molecular Weight 165.1891
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 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
Removal of tricaine methanesulfonate from aquaculture wastewater by adsorption onto pyrolysed paper mill sludge.
2017 Feb
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:22:18 GMT 2023
Edited
by admin
on Sat Dec 16 00:22:18 GMT 2023
Record UNII
971ZM8IPK1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICAINE METHANESULFONATE
WHO-DD  
Common Name English
Tricaine methanesulfonate [WHO-DD]
Common Name English
FINQUEL
Brand Name English
ETHYL M-AMINOBENZOATE METHANESULFONATE
Systematic Name English
TRICAINE MESILATE [MART.]
Common Name English
TRICAINE METHANESULFONATE [GREEN BOOK]
Common Name English
3-AMINOBENZOIC ACID ETHYL ESTER METHANESULFONATE
Systematic Name English
METACAINE MESYLATE
Common Name English
TRICAINE MESYLATE
Common Name English
TRICAINE MESILATE
MART.  
Common Name English
MS-222
Code English
BENZOIC ACID, 3-AMINO-, ETHYL ESTER, METHANESULFONATE (1:1)
Common Name English
NSC-93790
Code English
TS-222
Code English
TRICAINE [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QN01AX93
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
Code System Code Type Description
FDA UNII
971ZM8IPK1
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-956-8
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
NSC
93790
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
DRUG BANK
DBSALT002874
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
DAILYMED
971ZM8IPK1
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
CAS
886-86-2
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
SMS_ID
300000023852
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
PUBCHEM
13454
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022133
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
RXCUI
1492443
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
TRICAINE MESYLATE
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY
MERCK INDEX
m11056
Created by admin on Sat Dec 16 00:22:18 GMT 2023 , Edited by admin on Sat Dec 16 00:22:18 GMT 2023
PRIMARY Merck Index
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ACTIVE MOIETY