Skip to Content
MilliporeSigma
All Photos(1)

Documents

C4382

Sigma-Aldrich

Carbamoylcholine chloride

≥98% (titration), crystalline

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

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

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)

Looking for similar products? Visit Product Comparison Guide

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.

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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 6

1 of 6

(±)-Muscarine chloride hydrate ≥98% (HPLC)

Sigma-Aldrich

M104

(±)-Muscarine chloride hydrate

Tubocurarine hydrochloride pentahydrate ≥97%

Sigma-Aldrich

T2379

Tubocurarine hydrochloride pentahydrate

Ceftiofur VETRANAL®, analytical standard

Supelco

34001

Ceftiofur

Oxotremorine M solid

Sigma-Aldrich

O100

Oxotremorine M

Atropine sulfate salt monohydrate ≥97% (TLC), crystalline

Sigma-Aldrich

A0257

Atropine sulfate salt monohydrate

4-DAMP ≥98% (HPLC)

Sigma-Aldrich

SML0255

4-DAMP

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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service