Tricaine mesylate

Tricaine mesylate
Clinical data
Other names	Metacaine; Tricaine; MS-222; Finquel; TMS
ATCvet code	QN01AX93 (WHO) ;
Identifiers
	IUPAC name Ethyl 3-aminobenzoate methanesulfonic acid;
CAS Number	886-86-2 ;
PubChem CID	13454;
ChemSpider	12878 ;
UNII	971ZM8IPK1;
CompTox Dashboard (EPA)	DTXSID6022133 ;
ECHA InfoCard	100.011.779
Chemical and physical data
Formula	C10H15NO5S
Molar mass	261.29 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	149.5 °C (301.1 °F)
	SMILES [NH3+]C1=CC=CC(C(OCC)=O)=C1.CS(=O)([O-])=O;
	InChI 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) ; Key:FQZJYWMRQDKBQN-UHFFFAOYSA-N ;
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Tricaine mesylate (Tricaine methanesulfonate, TMS, MS-222, Tricaine-S, Aqualife TMS), is white powder used for anesthesia, sedation, or euthanasia of fish. TMS is the only anesthetic licensed in the United States for fin fish that are intended for human consumption. The drug can have selective toxicity for poikilotherms due to their lower rate of metabolism in the liver.[1]

TMS is an anaesthetic that operates by preventing sodium ions to enter the cell and thus silencing action potentials.[2] This has the net effect of blocking signal exchange between the brain and extremities.

The largest manufacturer of Tricaine-S is Syndel in Ferndale, WA, in the USA.[3] Tricaine-S is used for handling fish, amphibians, and other cold-blooded animals during manual spawning, as well as during marking, measuring, photography, research, surgical operations, transport, and weighing of fish.

The optimum concentration may vary with the size and species of the fish, and other variables.

It is easily soluble in water (both fresh and salt) but it drastically decreases the pH of water, increasing the acidity, which may be toxic for fish. Sodium bicarbonate can be used to buffer the solution to a pH range of 6.5-7.5. Usually an equal amount of buffer is added to attain a neutral pH.[4] In salt/marine/sea water, the buffer use may not be necessary because sea water itself has buffering capacity.

The solution of TMS needs to be prepared freshly each time because TMS is light-sensitive and might form toxic by-products upon exposure to light.

References

Wayson KA, Downes H, Lynn RK, Gerber N (September 1976). "Studies on the comparative pharmacology and selective toxicity of tricaine methanesulfonate: metabolism as a basis of the selective toxicity in poikilotherms". The Journal of Pharmacology and Experimental Therapeutics. 198 (3): 695–708. PMID 185356.
https://link.springer.com/article/10.1007/s11160-010-9188-0
"Tricaine-S (MS-222) Fish Anesthetic | Aqualife TMS Fish Sedative". Syndel. Retrieved 2019-12-12.
Brown C, Pavek T. "Fish and Amphibian Euthanasia". In Bowser P (ed.). Animal Care and Use Procedure (ACUP) (PDF). Cornell University. Archived from the original (PDF) on 13 June 2015.

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[pmid185356-1] Wayson KA, Downes H, Lynn RK, Gerber N (September 1976). "Studies on the comparative pharmacology and selective toxicity of tricaine methanesulfonate: metabolism as a basis of the selective toxicity in poikilotherms". The Journal of Pharmacology and Experimental Therapeutics. 198 (3): 695–708. PMID 185356.

[2] ttps://link.springer.com/article/10.1007/s11160-010-9188-0

[3] "Tricaine-S (MS-222) Fish Anesthetic | Aqualife TMS Fish Sedative". Syndel. Retrieved 2019-12-12.

[4] Brown C, Pavek T. "Fish and Amphibian Euthanasia". In Bowser P (ed.). Animal Care and Use Procedure (ACUP) (PDF). Cornell University. Archived from the original (PDF) on 13 June 2015.