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1866-15-5

1866-15-5 Structure

1866-15-5 Structure
IdentificationMore
[Name]

ACETYLTHIOCHOLINE IODIDE
[CAS]

1866-15-5
[Synonyms]

2-ACETOTHIOETHYLTRIMETHYLAMMONIUM IODIDE
[2-(ACETYLTHIO)ETHYL](TRIMETHYL)AMMONIUM IODIDE
(2-MERCAPTOETHYL)TRIMETHYLAMMONIMUM IODIDE ACETATE
(2-MERCAPTOETHYL)TRIMETHYLAMMONIUM IODIDE ACETATE
2-(THIOACETYLOXY)-N,N,N-TRIMETHYLETHANAMINIUM IODIDE
ACETYLTHIOCHOLINE IODIDE
N-(2-MERCAPTOETHYL)TRIMETHYLAMMONIUM IODIDE ACETATE
S-ACETYLTHIOCHOLINE IODIDE
THIOCHOLINE IODIDE ACETATE
(2-mercaptoethyl)trimethyl-ammoniuiodideacetate
2-(acetylthio)-n,n,n-trimethyl-ethanaminiuiodide
2-(acetylthio)-n,n,n-trimethylethanaminiumiodide
acetylthiocholinediiodide
Ethanaminium,2-(acetylthio)-N,N,N-trimethyl-,iodide
S-[2-(trimethyl-lambda5-azanyl)ethyl] ethanethioate hydroiodide
s-acetylthio-choliniodide
Acetylthiocholinjodid
S-ACETYLTHIOCHOLINE IODIDE extrapure AR substrate for acetylcholinesterase
[EINECS(EC#)]

217-474-1
[Molecular Formula]

C7H16INOS
[MDL Number]

MFCD00011819
[Molecular Weight]

289.18
[MOL File]

1866-15-5.mol
Chemical PropertiesBack Directory
[Appearance]

white crystalline powder
[Melting point ]

205-210 °C(lit.)
[density ]

1.4885 (estimate)
[storage temp. ]

2-8°C
[solubility ]

H2O: 100 mg/mL
[form ]

powder
[color ]

white
[Sensitive ]

Light Sensitive & Hygroscopic
[Detection Methods]

TITR
[BRN ]

3916578
[InChI]

InChI=1S/C7H16NOS.HI/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1
[InChIKey]

NTBLZMAMTZXLBP-UHFFFAOYSA-M
[SMILES]

[N+](C)(C)(C)CCSC(=O)C.[I-]
[CAS DataBase Reference]

1866-15-5(CAS DataBase Reference)
[Storage Precautions]

Light sensitive
[EPA Substance Registry System]

Ethanaminium, 2-(acetylthio)-N,N,N-trimethyl-, iodide (1866-15-5)
Safety DataBack Directory
[Hazard Codes ]

T,Xi
[Risk Statements ]

R21:Harmful in contact with skin.
R25:Toxic if swallowed.
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 .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

FZ9865000
[F ]

3-8-10
[TSCA ]

Yes
[HazardClass ]

6.1
[PackingGroup ]

III
[HS Code ]

29309090
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->Diethyl ether-->Dichloromethane-->Thionyl chloride-->Acetic anhydride-->Acetone-->Sodium bicarbonate-->Iodomethane-->Thiourea-->2-Dimethylaminoethanol-->2-DIMETHYLAMINOETHANETHIOL HYDROCHLORIDE-->Potassium thioacetate
Hazard InformationBack Directory
[Description]

Acetylthiocholine iodide, also known as ATCI, serves as both an acetylcholinesterase (AChE) substrate and a nicotinic acetylcholine receptor (AChR) agonist. ATCI itself is a colorless and odorless compound. It exhibits solubility in both water and ethanol. It is a synthetic compound extensively employed in laboratory experiments to measure the activity of AChE, a vital enzyme responsible for the breakdown of the neurotransmitter acetylcholine (ACh) in the central and peripheral nervous systems. Additionally, it enables the evaluation of drug effects on AChE activity and facilitates investigations into the impact of toxins on the nervous system. Acetylthiocholine iodide functions as an inhibitor of AChE. By binding to the enzyme′s active site, it prevents AChE from catalyzing the breakdown of ACh. Consequently, ACh accumulates in the synaptic cleft, leading to increased neuron excitability. This inhibition of AChE by ATCI ultimately results in a higher ACh concentration within the synaptic cleft, yielding a range of physiological effects. These effects encompass heightened muscle contraction, increased heart rate and blood pressure, elevated salivation, intensified bronchial secretions, and augmented gastrointestinal activity[1].
[Chemical Properties]

white crystalline powder
[Uses]

A nAChR agonist and substrate of acetylcholinesterase
[Purification Methods]

Recrystallise the iodide from propan-1-ol (or iso-PrOH, or EtOH/Et2O) until almost colourless and dry it in a vacuum desiccator over P2O5. Its solubility in H2O is 1% w/v. A 0.075M (21.7mg/mL) solution in 0.1M phosphate buffer pH 8.0 is stable for 10-15 days if kept refrigerated. Store it away from light. It is commercially available as a 1% solution in H2O. [Ellman et al. Biochemical Pharmacology 7, 88 1961, IR: Hansen Acta Chem Scand 13 151 1959, 11 537 1957, Clin Chim Acta 2 316 1957, Ivin Zh Obshch Khim 22 267 1952, Beilstein 4 III 726, 4 IV 1585.]
[References]

[1] Madalina-Petruta Bucur, Gabriel-Lucian Radu, Bogdan Bucur. “Critical evaluation of acetylthiocholine iodide and acetylthiocholine chloride as substrates for amperometric biosensors based on acetylcholinesterase.” Sensors 13 2 (2013): 1603–13.
Spectrum DetailBack Directory
[Spectrum Detail]

ACETYLTHIOCHOLINE IODIDE(1866-15-5)MS
ACETYLTHIOCHOLINE IODIDE(1866-15-5)1HNMR
ACETYLTHIOCHOLINE IODIDE(1866-15-5)13CNMR
ACETYLTHIOCHOLINE IODIDE(1866-15-5)IR1
ACETYLTHIOCHOLINE IODIDE(1866-15-5)IR2
ACETYLTHIOCHOLINE IODIDE(1866-15-5)Raman
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

S-Acetylthiocholine iodide, 98%(1866-15-5)
[Alfa Aesar]

S-Acetylthiocholine iodide, 98%(1866-15-5)
[Sigma Aldrich]

1866-15-5(sigmaaldrich)
[TCI AMERICA]

Acetylthiocholine Iodide,>98.0%(T)(1866-15-5)
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