C4382

Carbamoylcholine chloride

≥98% (titration), crystalline

• Synonym(s): (2-Hydroxyethyl)trimethylammonium chloride carbamate, Carbachol, Carbamylcholine chloride
• 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

Properties

• 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

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.

Safety Information

• 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_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges