[2-(acetyloxy)ethyl]trimethylazanium chloride

• ChemBase ID: 53477
• Molecular Formular: C7H16ClNO2
• Molecular Mass: 181.66044
• Monoisotopic Mass: 181.08695644
• SMILES: [N+](CCOC(=O)C)(C)(C)C.[Cl-]
• Canonical SMILES: CC(=O)OCC[N+](C)(C)C.[Cl-]
• InChI: InChI=1S/C7H16NO2.ClH/c1-7(9)10-6-5-8(2,3)4;/h5-6H2,1-4H3;1H/q+1;/p-1
• InChIKey: JUGOREOARAHOCO-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(acetyloxy)ethyl]trimethylazanium chloride
• IUPAC Traditional name: acetylcholine chloride
• Synonyms: 2-(Acetyloxy)-N,N,N-trimethylethanaminium chloride; Acetylcholine chloride; Acetylcholine chloride; 2-Acetoxy-N,N,N-trimethylethanium chloride; 2-Acetyloxy-N,N,N-trimethylethanium chloride; 2-(Acetyloxy)-N,N,N,-trimethylethanaminium Chloride; Arterocoline; Miochol; Ovisot; Acetylcholini chloridum; Acecoline; ACh; 氯化乙酰胆碱; 氯化乙酰胆碱

Database IDs

• CAS Number: 60-31-1
• EC Number: 200-468-8
• MDL Number: MFCD00011698
• Beilstein Number: 3571875
• Merck Index: 1487
• PubChem SID: 24891113; 24890686; 24845420; 24891228; 162058240
• PubChem CID: 6060

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -4.2211437
• LogD (pH = 7.4): -4.2211437
• Log P: -4.2211437
• Molar Refractivity: 51.3455 cm^3
• Polarizability: 15.861634 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble; H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble100 mg/mL
• Melting Point: 146-150 °C(lit.); 148-150 °C; 148-153 °C; 149-152; 149-152°C

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen; -20°C
• Storage Warning: Hygroscopic; IRRITANT
• RTECS: FZ9800000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 2
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26; 26-37-60; S:20-25-26-37/39
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335; H315-H319-H335-H303
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: room temp

Product Information

• Purity: ~99%; ≥98.0% (AT); ≥99% (TLC); ≥99.0% (AT); 98+%
• Grade: Ph Eur; purum
• Salt Data: chloride
• Packaging: pkg of 150 mg (per vial)
• Suitability: suitable as substrate for acetylcholinesterase test; suitable for cell culture
• Ignition Residue: ≤0.05%
• Cation Traces: Ca: ≤20 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤50 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Linear Formula: (CH3)3N+CH2CH2OCOCH3Cl-

DETAILS

MP Biomedicals - 02194602

Cell Culture Reagent
Crystalline
Purity: ~99%

MP Biomedicals - 02100012

Crystalline Purity: ~99%

Selleck Chemicals - S1805

Research Area: Neurological Disease
Biological Activity:
The chemical compound acetylcholine (ACh) is a neurotransmitter in both the peripheral nervous system (PNS) and central nervous system (CNS) in many organisms including humans. Acetylcholine is one of many neurotransmitters in the autonomic nervous system (ANS) and the only neurotransmitter used in the motor division of the somatic nervous system. [1]

Sigma Aldrich - A6625

Application
Do you have application information on this product that you would like to share?
Caution
Very hygroscopic
包装
10 mg in autosmp vl
25, 100, 500 g in glass bottle
Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Sigma Aldrich - A9101

Application
For use as a substrate to determine acetylcholinesterase activity.
Reconstitution
Reconstituted solution is stable for 2 weeks when stored at 2-8 °C
Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Sigma Aldrich - A2661

Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Sigma Aldrich - 01018

Other Notes
Hydrolysis by acetylcholinesterase2; Base-catalysed hydrolysis in the presence of surfactants3; Kinetic parameters of acetylcholinesterase-catalyzed hydrolysis4
Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Sigma Aldrich - 01020

Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Sigma Aldrich - 03067

Biochem/physiol Actions
Acetylcholine chloride, injected at 20 mg/kg body weight, reduces mortality and plasma proinflammatory cytokines in mice with experimentally-induced sepsis 1. The cholinergicanti-infl ammatory mechanism is probably mediated by interaction of acetylcholine with α7n cholinoreceptor on monocytes, macrophages, and neutrophils, which decreases the levels of proinflammatory cytokines such as TNF-α, IL-1β, and IL-6.

Toronto Research Chemicals - A172060

Acetylcholine Chloride is a cholinergic.

REFERENCES

• http://en.wikipedia.org/wiki/Acetylcholine_chloride
• Molitor, H., et al.: J. Pharmacol. Exp. Ther., 58, 337 (1936)