| Identification | More | [Name]
Tricaine methanesulfonate | [CAS]
886-86-2 | [Synonyms]
3-AMINOBENZOIC ACID ETHYL ESTER METHANESULFONATE
3-AMINOBENZOIC ACID ETHYL ESTER METHANESULFONATE SALT
3-AMINOBENZOIC ACID ETHYL ESTER METHANESULFONIC SALT
3-Ethoxycarbonylanilinium methanesulphonate
Amid-Thin W
ETHYL 3-AMINOBENZOATE METHANESULFONATE
ETHYL 3-AMINOBENZOATE, METHANESULFONIC ACID SALT
ETHYL M-AMINOBENZOATE METHANESULFONATE
ETHYL M-AMINOBENZOATE METHANESULFONATE SALT
ETHYL M-AMINOBENZOATE METHANESULFONIC ACID SALT
M-AMINOBENZOIC ACID ETHYL ESTER METHANESULFONATE SALT
MS-22
MS-222
NAA Amide
Naphthaleneacetamide
Naphthyl acetamide
TRICAIN
TRICAINE
TRICAINE METHANESULFONATE
TRICAINE METHANSULFONATE | [EINECS(EC#)]
212-956-8 | [Molecular Formula]
C7H15NO7S | [MDL Number]
MFCD00013176 | [Molecular Weight]
257.26 | [MOL File]
886-86-2.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO OFF-WHITE FINE POWDER | [Melting point ]
146-149 °C(lit.)
| [density ]
1.3799 (rough estimate) | [refractive index ]
1.5060 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL, clear, colorless
| [form ]
Fine Powder | [color ]
White to off-white | [Merck ]
9621 | [BRN ]
3775022 | [Major Application]
forensics and toxicology
pharmaceutical (small molecule) | [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) | [InChIKey]
FQZJYWMRQDKBQN-UHFFFAOYSA-N | [SMILES]
C1(C=CC=C(N)C=1)C(=O)OCC.S(=O)(=O)(O)C | [Uses]
The anesthetic of choice for amphibians is tricaine methanesulfonate (MS - 222, tricaine, FINQUEL, Argent Chemical Laboratories, Redmond, WA) (Wright 2001f ). It is a white crystalline powder that may be mixed with water to anesthetize fi sh and amphibians. Amphibians are immersed in a bath of tricaine methanesulfonate until anesthesia is achieved and then maintained in fresh water for the particular procedure to be performed. For longer procedures, the patient may be immersed in a 50% dilution of the original induction solution or intubated and maintained on isofl urane. | [CAS DataBase Reference]
886-86-2(CAS DataBase Reference) | [EPA Substance Registry System]
886-86-2(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335-H412 | [Precautionary statements ]
P273-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
DG2455000
| [F ]
10 | [TSCA ]
TSCA listed | [HS Code ]
29224999 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Aquatic Chronic 3
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
LC50 (96hr) in rainbow trout: 50.50 mg/l (McKim) |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO OFF-WHITE FINE POWDER | [Definition]
ChEBI: A methanesulfonate salt obtained by reaction of tricaine with one molar equivalent of methanesulfonic acid. Used as an anaesthetic for fish. | [General Description]
Ethyl 3-aminobenzoate methanesulfonate is mainly used as an anesthetic for fish. It is also used for the euthanasia of all fish species especially zebrafish, which is commonly used in research. | [Biological Activity]
ethyl 3-aminobenzoate can block the generation of action potentials via voltage-dependent na+-channels.sodium channels play a critical role in physiology: they can rapidly transmit depolarizing impulses throughout cells and cell networks, therefore enabling co-ordination of higher processes. sodium channels are also of special importance for the history of physiology. | [in vitro]
the major mode of action for ethyl 3-aminobenzoate was found to be nervous system suppression whereby the entrance of sodium into the nerve was inhibited, therefore limiting nerve membrane excitability. in addition, the nerve inhibition was facilitated by the lipid solubility of ethyl 3-aminobenzoate, which allowed it to move easily into the cell membrane to bind with sodium channels [1]. | [in vivo]
previous study evaluated the potency and dynamics of ethyl 3-aminobenzoate-induced effects on neuronal firing of sensory and motor nerves alongside a defined motor behavior in xenopus laevis tadpoles. electrophysiological recordings of extraocular motor discharge and nerve activity were measured before, during and after administration of drugs. results showed that ethyl 3-aminobenzoate and benzocaine, but not pancuronium could cause a dose-dependent, reversible blockade of extraocular motor and sensory nerve activity. such results indicated that ethyl 3-aminobenzoate was able to block the activity of both sensory and motor nerves compatible with the mechanistic action of effective anesthetics, suggesting that ethyl 3-aminobenzoate was effective as single-drug anesthetic for surgical interventions in anamniotes [2]. | [References]
[1] k. m. carter, c. m. woodley and r. s. brown. a review of tricaine methanesulfonate for anesthesia of fish. rev. fish biol. fisheries 21, 51-59 (2011).
[2] c. ramlochansingh, f. branoner, b. p. chagnaud, et al. efficacy of tricaine methanesulfonate (ms-222) as an anesthetic agent for blocking sensory-motor responses in xenopus laevis tadpoles. plos one 9(7), e101606 (2014). |
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