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C4382 Sigma-Aldrich

Carbamoylcholine chloride

≥98% (titration), crystalline

Synonym: (2-Hydroxyethyl)trimethylammonium chloride carbamate, Carbachol, Carbamylcholine chloride

  • CAS Number 51-83-2

  • Linear Formula NH2COOCH2CH2N(Cl)(CH3)3

  • Molecular Weight 182.65

  •  Beilstein/REAXYS Number 3917459

  •  EC Number 200-127-3

  •  MDL number MFCD00012011

  •  PubChem Substance ID 24277829

  •  NACRES NA.77

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Properties

Related Categories Agonists, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, C-CH, Cell Biology,
InChI Key   AIXAANGOTKPUOY-UHFFFAOYSA-N
assay   ≥98% (titration)
form   crystalline
color   white
mp   210 °C (dec.) (lit.)
solubility   H2O: 1 g/mL
  ethanol: 20 mg/mL
Gene Information   human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133), CHRNA2(1135)
mouse ... Chrm1(12669)
rat ... Chrm1(25229), Chrm2(81645), Chrm3(24260), Chrna2(170945), Chrna3(25101), Chrna4(25590)

Description

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

Packaging

1 g in poly tube

10, 25 g in poly bottle

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 also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGII
WGK Germany 
3
RTECS 
GA0875000

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Frequently Asked Questions

Which document(s) contains shelf-life or expiration date information for a given product?
If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.
How do I get lot-specific information or a Certificate of Analysis?
The lot specific COA document can be found by entering the lot number above under the "Documents" section.
What is the difference between Carbamoylcholine chloride Products C4382 and C2409?
C4382 (98%) and C2409 (99%) are the same chemical with slightly different purity specifications. Product No. C2409 is no longer available.
How should Carbamoylcholine chloride, Product C4382, be dissolved?
This product is soluble in water (1000 mg/mL), in ethanol (20 mg/mL), and in methanol (100 mg/mL).
How do I find price and availability?
There are several ways to find pricing and availability for our products.Once you log onto our website, you will find the price and availability displayed on the product detail page.You can contact any of our Customer Sales and Service offices to receive a quote. USA customers: 1-800-325-3010 orview local office numbers.
What is the Department of Transportation shipping information for this product?
Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.
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Protocols & Articles
Peer-Reviewed Papers
15

References

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