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HomeProduct name listAcetylthiocholine iodide

Acetylthiocholine iodide

Synonym(s):(2-Mercaptoethyl)trimethylammonium iodide acetate

  • CAS NO.:1866-15-5
  • Empirical Formula: C7H16INOS
  • Molecular Weight: 289.18
  • MDL number: MFCD00011819
  • EINECS: 217-474-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-28 16:48:35
Acetylthiocholine iodide Structural

What is Acetylthiocholine iodide?

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

The Uses of Acetylthiocholine iodide

Acetylthiocholine iodide has been used as a substrate in the preparation of acetylcholine esterase (AChE) assay working solution for AChE activity assay. It has also been used as a component in phosphate buffer (PB) for cholinesterase assay.

The Uses of Acetylthiocholine iodide

A nAChR agonist and substrate of acetylcholinesterase

The Uses of Acetylthiocholine iodide

Substrate for the colorimetric determination of acetylcholinesterase activity.

What are the applications of Application

Acetylthiocholine iodide is 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.

Properties of Acetylthiocholine iodide

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
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
CAS DataBase Reference 1866-15-5(CAS DataBase Reference)
EPA Substance Registry System Ethanaminium, 2-(acetylthio)-N,N,N-trimethyl-, iodide (1866-15-5)

Safety information for Acetylthiocholine iodide

Signal word Danger
Pictogram(s)
ghs
Skull and Crossbones
Acute Toxicity
GHS06
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P270:Do not eat, drink or smoke when using this product.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

Computed Descriptors for Acetylthiocholine iodide

InChIKey NTBLZMAMTZXLBP-UHFFFAOYSA-M
SMILES [N+](C)(C)(C)CCSC(=O)C.[I-]

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