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C4382

Carbamoylcholine chloride

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

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:
51-83-2
Molecular Weight:
182.65
EC Number:
200-127-3
NACRES:
NA.77
PubChem Substance ID:
24277829
UNSPSC Code:
12352200
MDL number:
MFCD00012011
Beilstein/REAXYS Number:
3917459
Assay:
≥98% (titration)
Form:
crystalline
Quality level:
100
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Product Name

Carbamoylcholine chloride, ≥98% (titration), crystalline

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)

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.

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pictograms

Skull and crossbones
GHS06

signalword

Danger

hcodes

H300

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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG5823
BCCG5821
BCCD7226
BCCC2414
BCBZ9113

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BMP4-BMPR1A signaling in beta cells is required for and augments glucose-stimulated insulin secretion
Goulley J, et al.
Cell Metabolism, 5(3), 207-219 (2007)
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)
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
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Global Trade Item Number

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