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C4382

Carbamoylcholine chloride

≥98% (titration), Non-selective cholinergic agonist, crystalline

Carbamoylcholine chloride
1 of 2 reviewers received a sample product or took part in a promotion

Synonym(s):

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

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About This Item

Linear Formula:
NH2COOCH2CH2N(Cl)(CH3)3
CAS Number:
Molecular Weight:
182.65
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
200-127-3
MDL number:
Beilstein/REAXYS Number:
3917459
Assay:
≥98% (titration)
Form:
crystalline
Quality level:
Pricing and availability is not currently available.
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Product Name

Carbamoylcholine chloride, ≥98% (titration), crystalline

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

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

Non-selective cholinergic agonist that is resistant to the action of cholinesterases; inhibits apoptotic death of cultured neurons, and may induce apoptosis in thymocytes.
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.

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.

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This Item
A22512697826978
form

crystalline

form

powder

form

powder or crystals

form

powder or crystals

assay

≥98% (titration)

assay

≥98% (TLC)

assay

≥99.0% (AT)

assay

≥99.0% (AT)

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

200

solubility

H2O: 1 g/mL, ethanol: 20 mg/mL

solubility

H2O: 50 mg/mL (solutions undergo rapid, pH-dependent decomposition at pH > 6.)

solubility

H2O: 1 M, clear, colorless

solubility

H2O: 1 M, clear, colorless

color

white

color

-

color

colorless to white

color

colorless to white

mp

210 °C (dec.) (lit.)

mp

171-173 °C (lit.)

mp

302-305 °C (dec.) (lit.)

mp

302-305 °C (dec.) (lit.)


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pictograms

Skull and crossbones

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges



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Certificates of Analysis (COA)

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Role of the non-neuronal cholinergic system in the eye: a review
Duncan G and Collison DJ
Life Sciences, 72(18-19), 2013-2019 (2003)
Anne Cathrine Nøhr et al.
Scientific reports, 9(1), 3802-3802 (2019-03-09)
GPR139 is an orphan G protein-coupled receptor (GPCR) that is primarily expressed in the brain in regions known to regulate motor control and metabolism. Here, we screened a diverse 4,000 compound library in order to identify GPR139 agonists. We identified
Carbachol and nitric oxide inhibition of Na, K-ATPase activity in bovine ciliary processes
Ellis DZ, et al.
Investigative Ophthalmology & Visual Science, 42(11), 2625-2631 (2001)



Global Trade Item Number

SKUGTIN
C4382-25G04061832089799
C4382-1G04061835259595
C4382-10G04061833492048

Questions

1–3 of 3 Questions  
  1. What is the difference between Carbamoylcholine chloride Products C4382 and C2409?

    1 answer
    1. C4382 (98%) and C2409 (99%) are the same chemical with slightly different purity specifications. Product No. C2409 is no longer available.

      Helpful?

  2. How should Carbamoylcholine chloride, Product C4382, be dissolved?

    1 answer
    1. This product is soluble in water (1000 mg/mL), in ethanol (20 mg/mL), and in methanol (100 mg/mL).

      Helpful?

  3. What is the Department of Transportation shipping information for this product?

    1 answer
    1. 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.

      Helpful?

Reviews

Active Filters

  1. Pondicherry
    • Review 1
    • Votes 0
    3 out of 5 stars.

    SELF LIFE ?

    Kindly mention the Expiration date in your COA or SDS

    Helpful?

    1. Response from Merck KGaA:

      We do not issue an expiration date or shelf life to product C4382, this is common for many of our lab grade chemicals. We have determined the product is stable and could be good for years to come as long as it is stored properly. We warranty the product for one year from the date of shipment. See our product dating policy at the link below under Additional Useful Documents

      https://www.sigmaaldrich.com/US/en/life-science/quality-and-regulatory-management/quality-services

  2. 1 Ratings-only review