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C4382

Sigma-Aldrich

Carbamoylcholine chloride

≥98% (titration), crystalline

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Synonym(s):
(2-Hydroxyethyl)trimethylammonium chloride carbamate, Carbachol, Carbamylcholine chloride
Linear Formula:
NH2COOCH2CH2N(Cl)(CH3)3
CAS Number:
Molecular Weight:
182.65
Beilstein/REAXYS Number:
3917459
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

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

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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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 2 Oral

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’.

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4-DAMP ≥98% (HPLC)

Sigma-Aldrich

SML0255

4-DAMP

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)
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)
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)
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)

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