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C4382

Carbamoylcholine chloride

Name: Carbamoylcholine chloride
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24277829

UNSPSC Code:

12352200

EC Number:

200-127-3

MDL number:

MFCD00012011

Beilstein/REAXYS Number:

3917459

Assay:

≥98% (titration)

Form:

crystalline

Quality level:

100

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Properties

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)

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

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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pictograms

GHS06

signalword

Danger

hcodes

H300

pcodes

P264 - P270 - P301 + P310 - P405 - P501

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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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)

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)

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