2260-50-6

Basic information

• Product Name: ACETYLCHOLINE IODIDE
• Synonyms: N-(2-HYDROXYETHYL)TRIMETHYLAMMONIUM IODIDE ACETATE;2-(ACETYLOXY)-N,N,N-TRIMETHYLETHANAMINIUM IODIDE;2-ACETOXYETHYLTRIMETHYLAMMONIUM IODIDE;ACH;ACETYLCHOLINE IODIDE;2-(acetyloxy)-n,n,n-trimethyl-ethanamiuiodide;2-(acetyloxy)-n,n,n-trimethylethanamiumiodide;acetyl-choliniodide
• CAS NO: 2260-50-6
• Molecular Formula: C₇H₁₆NO₂*I
• Molecular Weight: 273.11
• EINECS: 218-862-3
• Product Categories: Substrates;Ammonium Iodides (Quaternary);Quaternary Ammonium Compounds
• Mol File: 2260-50-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: 161-164 °C
• Appearance: White/Crystalline Powder
• Density: 1.4816 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: almost transparency
• Sensitive: Light Sensitive & Hygroscopic
• BRN: 3571339
• CAS DataBase Reference: ACETYLCHOLINE IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETYLCHOLINE IODIDE(2260-50-6)
• EPA Substance Registry System: ACETYLCHOLINE IODIDE(2260-50-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: KH3300000
• F: 8-9
• TSCA: Yes
• Hazardous Substances Data: 2260-50-6(Hazardous Substances Data)

Usage

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

Acetylcholine is an endogenous neurotransmitter at cholinergic synapses that amplifies action potential of the sarcolemma thereby inducing muscle contractions. Acetylcholine iodide is used as an acetylcholine receptor agonist to identify, characterize and differentiate among types of cholinergic receptors. Acetylcholine iodide is used as a substrate to identify and characterize natural and mutated acetylcholinesterase(s).

Biochem/physiol Actions

Endogenous neurotransmitter at cholinergic synapses; amplifies action potential of the sarcolemma thereby inducing muscle contractions.

InChI:InChI=1/C7H16NO2.HI/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1

Synthetic route

2',6'-dihydroxy-4'-methylacetophenone (1634-34-0) + choline iodide (17773-10-3) → acetylcholine iodide (2260-50-6)

Conditions	Yield
at 65℃; for 2h; Temperature;	93%

2-iodoethyl acetate (627-10-1) + trimethylamine (75-50-3) → acetylcholine iodide (2260-50-6)

Conditions	Yield
With diethyl ether

acetylcholine iodide (2260-50-6) → acetate (71-50-1)

Conditions	Yield
In solid for 5h; Ambient temperature; Irradiation;

acetylcholine iodide (2260-50-6) → choline iodide (17773-10-3)

Conditions	Yield
With tacrine monohydrochloride; acetylcholinesterase In water; sodium chloride at 25℃; Thermodynamic data; ΔF, other concentration of substrate, other inhibitor;
With acetylcholinesterase In aq. buffer at 20℃; for 0.416667h; pH=7.8; Enzymatic reaction;
With pillar[5]arene; acetylcholinesterase at 37℃; for 1.5h; Reagent/catalyst;
With 5,5'-dithiobis-(2-nitrobenzoic acid); acetylcholinesterase enzyme from electrophorus electricus (electric eel) In aq. phosphate buffer at 20℃; for 0.25h; pH=8;

acetylcholine iodide (2260-50-6) → acetic acid (64-19-7)

Conditions	Yield
With water; tetramethlyammonium chloride; acetylcholinoesterase at 38℃; Rate constant; other monoquaternary ammonium salts containing hydrophobic radicals as inhibitors of acetylcholinoesterase activity;

acetylcholine iodide (2260-50-6) + C39H39N9O6 (417698-69-2) → C39H39N9O6*C7H16NO2(1+)*I(1-)

Conditions	Yield
In chloroform-d1; d(4)-methanol Equilibrium constant;

acetylcholine iodide (2260-50-6) + silver picrate (146-84-9) → acetylcholine picrate (77822-10-7)

carboxylatopillar[5]arene sodium salt + acetylcholine iodide (2260-50-6) → C55H40O30(10-)*10Na(1+)*C7H16NO2(1+)*I(1-)

Conditions	Yield
In water-d2 at 21.84℃;

pillar[5]arene + acetylcholine iodide (2260-50-6) → 10H3N*C7H16NO2(1+)*I(1-)*C55H50O30

Conditions	Yield
In water at 29.99℃;

acetylcholine iodide (2260-50-6) → choline (62-49-7)

Conditions	Yield
With human serum butyrylcholinesterase In aq. buffer pH=5; Kinetics; Reagent/catalyst; Enzymatic reaction;

acetylcholine iodide (2260-50-6) + C107H100O17 → C107H100O17*C7H16NO2(1+)*I(1-)

Conditions	Yield
In chloroform-d1; [D3]acetonitrile at 29.84℃;

acetylcholine iodide (2260-50-6) + C107H100O17 → C107H100O17*C7H16NO2(1+)*I(1-)

Conditions	Yield
In chloroform-d1; [D3]acetonitrile at 29.84℃;

Upstream product

• 627-10-1 2-iodoethyl acetate 
• 75-50-3 trimethylamine 
• 1634-34-0 2',6'-dihydroxy-4'-methylacetophenone 
• 17773-10-3 choline iodide 

Downstream Products

• 17773-10-3 choline iodide 
• 62-49-7 choline 
• 77822-10-7 acetylcholine picrate 

Relevant articles and documents

Synthesis method of pharmaceutical synthesis intermediate acetylcholine iodide

The invention relates to a synthesis method of a pharmaceutical synthesis intermediate acetylcholine iodide. The method mainly includes the steps of: adding 3mol 3, 5-dhydroxyl-4-acetyl toluene and 4-5mol choline iodide into a reaction container, controlling the stirring speed at 110-130rpm, raising the temperature to 60-65DEG C, maintaining the temperature and performing stirring continuously until complete dissolution, conducting standing for 90-120min, lowering the solution temperature to 10-15DEG C, precipitating crystals, performing filtration, washing the crystals with a cyclohexane solution and a toluene solution, and conducting dehydration with a dehydrating agent, thus obtaining the finished product acetylcholine iodide.