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C4382

Sigma-Aldrich

Carbamoylcholine chloride

≥98% (titration), crystalline

Synonym(s):
(2-Hydroxyethyl)trimethylammonium chloride carbamate, Carbachol, Carbamylcholine chloride
Linear Formula:
NH2COOCH2CH2N(Cl)(CH3)3
CAS Number:
Molecular Weight:
182.65
Beilstein:
3917459
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (titration)

form

crystalline

color

white

mp

210 °C (dec.) (lit.)

solubility

H2O: 1 g/mL
ethanol: 20 mg/mL

SMILES string

[Cl-].C[N+](C)(C)CCOC(N)=O

InChI

1S/C6H14N2O2.ClH/c1-8(2,3)4-5-10-6(7)9;/h4-5H2,1-3H3,(H-,7,9);1H

InChI key

AIXAANGOTKPUOY-UHFFFAOYSA-N

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Sigma-Aldrich

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assay

≥98% (titration)

assay

≥99% (TLC)

assay

≥98%

assay

≥95% (TLC)

form

crystalline

form

powder

form

crystals

form

powder

color

white

color

-

color

white

color

yellow to orange

solubility

H2O: 1 g/mL, ethanol: 20 mg/mL

solubility

water: 100 mg/mL, clear to slightly hazy, colorless

solubility

H2O: 50 mg/mL

solubility

DMSO: 2 mg/mL

Quality Level

100

Quality Level

200

Quality Level

300

Quality Level

100

mp

210 °C (dec.) (lit.)

mp

-

mp

302-305 °C (dec.) (lit.)

mp

213.0-214.0  °C

Application

Carbamoylcholine chloride has been used:
  • to stimulate insulin secretion in transgenic mice
  • to induce contraction of undifferentiated and differentiated human adipose-derived stem cells (hASCs)
  • to mediate constriction of iris in pupillary light reflex studies in mice

Biochem/physiol Actions

Carbachol elicits tear fluid secretion by interacting with muscarinic receptors. It is an analog of acetylcholine and an antiglaucoma drug. In ciliary processes, carbachol along with nitric oxide (NO) regulates Na+ and K+-ATPase activity. It stimulates insulin vesicles transport to the secretory site to increase insulin secretion.
Non-selective cholinergic agonist that is resistant to the action of cholinesterases; inhibits apoptotic death of cultured neurons, and may induce apoptosis in thymocytes.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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