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C4382

Sigma-Aldrich

Carbamoylcholine chloride

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

≥98% (titration), crystalline

Synonym(s):

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

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$276.00
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$747.00
25 G
$1,340.00

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1 G
$276.00
10 G
$747.00
25 G
$1,340.00

About This Item

Linear Formula:
NH2COOCH2CH2N(Cl)(CH3)3
CAS Number:
51-83-2
Molecular Weight:
182.65
Beilstein:
3917459
EC Number:
200-127-3
MDL number:
MFCD00012011
UNSPSC Code:
12352200
PubChem Substance ID:
24277829
NACRES:
NA.77

$276.00

Please contact Customer Service for Availability
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Quality Level

100

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

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)

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Application

Carbamoylcholine chloride has been used:
  • to stimulate insulin secretion in transgenic mice[1]
  • to induce contraction of undifferentiated and differentiated human adipose-derived stem cells (hASCs)[2]
  • to mediate constriction of iris in pupillary light reflex studies in mice[3]

Biochem/physiol Actions

Carbachol elicits tear fluid secretion by interacting with muscarinic receptors.[4] 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.[5] It stimulates insulin vesicles transport to the secretory site to increase insulin secretion.[1]
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
GHS06

Signal Word

Danger

Hazard Statements

H300

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0644
BCCH5511
BCCJ5652
BCCG5823
BCCG5821

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Proteomic profiling of tissue-engineered blood vessel walls constructed by adipose-derived stem cells
Wang C, et al.
Tissue Engineering: Part A, 19(3-4), 415-425 (2012)
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)
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
Targeted mutation of the calbindin D28k gene selectively alters nonvisual photosensitivity
Butler MP, et al.
The European Journal of Neuroscience, 33(12), 2299-2307 (2011)
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2 Reviews This action will navigate to reviews.

Questions

1–3 of 3 Questions  

  1. 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?

  2. 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?

  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

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

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 MilliporeSigma:

      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

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