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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
MOL RATIO 1 MOL RATIO (average)
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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
971ZM8IPK1
Record Status Validated (UNII)
Record Version